Synthesis and biological evaluation of some undecanone derivatives

MEDICINAL

CHEMISTRY

RESEARCH

Med Chem Res

DOI 10.1007/s00044-017-2006-7

ORIGINAL RESEARCH

Synthesis and biological evaluation of some undecanone

derivatives

1

Suryachandra Rao Ravada¹Harikrishna Kancharla¹

●

Bharani Meka

Trimurtulu Golakoti¹

Received: 8 July 2015 / Accepted: 27 July 2017

Abstract The total synthesis of Ardisinone E [15, 1-(2,4,6-

trihydroxy phenyl)-11-(2-hydroxyphenyl)-undecan-1-one],

a natural diarylundecanone, isolated from Ardisia arbor-

escens, was accomplished along with 16 new diarylunde-

canone analogs (18a–p), by modiﬁed Wittig reaction. The

structures of the compounds were conﬁrmed by ¹H, ¹³C and

mass spectral data. Compound 15 showed potent cytotoxic

activity with an ED₅₀of 4.19 µg/mL in brine shrimp leth-

ality assay model. Compounds 18c, 18e, 18j, 18k, 18l, and

18m exhibited strong anti-oxidant activity with IC₅₀values

of 18.75, 12.28, 18.35, 11.04, 12.05, and 11.32 µg/mL,

respectively, in NBT free radical assay. Compounds 18e,

18k, and 18m also showed signiﬁcant 5-lipoxyganase

enzyme inhibitory potential with IC₅₀values of 12.8, 15.23,

and 15.23 µg/mL, respectively.

Introduction

The plants of myristicaceae family are rich source of diaryl-

alkanones which include diarylpropanoids (Isogai et al.

1973; Forrest et al. 1970; Forrest et al. 1974), diarylpenta-

noids (Knerachelin A & D) (Zahir et al. 1993), diarylno-

nanoids (Malabaricones A-D) (Purushothaman et al. 1977;

Orabi et al. 1991; Cooray et al. 1987; Kumar et al. 1988;

Zahir et al. 1993; Pinto et al. 1988) and diarylundecanoids

(Lopes et al. 1982). Myristica fragrans and Myristica

malabarica have been used in several Asian countries as the

folk medicine (Jayaweera 1982) and as exotic spice in

various Indian cuisines. The genus Ardisia of myristicaceae

family includes more than 200 species. Plants of Ardisia are

used in Chinese traditional medicine to cure pulmonary

tuberculosis, hepatitis, chronic bronchitis and menstrual

problems. Ardisinone E [15, 1-(2,4,6-trihydroxy phenyl)-

11-(2-hydroxyphenyl)-undecan-1-one], a natural metabolite

belonging to the class of compounds known as diary-

lundecanones, were isolated from Ardisia arborescens

(Ying Zheng et al. 2004).

●

Keywords Ardisinone Diarylundecanone Ardisia

●

arborescens 5-lipoxyganase Brine shrimp

Natural occurrence of diarylundecanones is relatively

less known and their biological effects have not been

explored. Diarylnonanones possess wide range of biological

activities and due to the close structural similarity of dia-

rylundecanones with diarylnonanones the former are pre-

sumed to exhibit similar biological activities. This has

prompted us to attempt the total synthesis of ardisinone E

(15), a diarylundecanone derivative and evaluate its biolo-

gical potential. In this process, we have also synthesized

sixteen new diarylundecanones (18a–p) and screened them

for their anti-oxidant, anti-inﬂammatory, and cytotoxicity

potential.

Electronic supplementary material The online version of this article

(doi:10.1007/s00044-017-2006-7) contains supplementary material,

which is available to authorized users.

* Bharani Meka

bharanimeka81@gmail.com

1

Laila Impex R & D Centre, Unit-I, Phase-III, Jawahar autonagar,

Vijayawada 520 007 Andhra Pradesh, India

Med Chem Res

OH

O

R₁

R₄

O

R₈

R₆

R₂

R₃

15

18a-p

R₅

R₇

HO

OH

O

R₈

OH

R₁

OH

R₂

R₃

COOH

CHO

17a-p

4

R₅

R₇

12a

HO

OH

R₄

R₆

OH

O

R₈

R₆

R₁

R₄

CHO

R₂

R₃

CHO

3

2

10a

6a

10 b-e

R₅

R₇

O

CHO

Scheme 2 Retrosynthetic analysis of undecanones (18a–18p)

OH

H₃CO

CHO

O

3

O

approach as summarized in Scheme 2 was envisaged for

compounds of general diarylundecanone skeleton and the

synthesis of derivatives 18a–p was accomplished by

adopting the synthetic scheme depicted in Scheme 5.

The sequential disconnection Scheme 2 reveals that the

enone intermediate (17a–p) could be the most advanced

precursor for substituted diarylundecanone compounds.

Further disconnection of this precursor between the α and β

oleﬁnic carbons of enone moiety leads to 9-(substituted

phenyl)-nonanal (10) and commercially available sub-

stituted acetophenone as the advanced precursors. Further

disconnection analysis revealed that aryl substituted 9-(2-

hydroxyphenyl)-nonanal analogs (10b–e) can be produced

from ε-caprolactone based on the same retrosynthetic

strategy as described in Scheme 1.

Scheme 1 Retrosynthetic analysis of ardisinone E

Results and discussion

The total synthesis of ardisinone E was envisaged based on

the retro synthetic analysis of diarylundecanone skeleton as

depicted in Scheme 1. The disconnection approach revealed

that phloroglucinol and 11(2-hydroxyphenyl)-undecanoic

acid (12a) are the immediate precursors of ardisinone E. In

addition, 9(2-hydroxyphenyl)-nonanal (10a) and 7(2-

hydroxyphenyl)-heptanal (6a) are identiﬁed as other key

intermediates in retro synthesis. Salicylaldehyde and methyl

6-al-hexanoate (3) are in turn the appropriate precursors for

7(2-hydroxyphenyl)-heptanal (6a). Finally ε-caprolactone

can be the earliest precursor in the synthetic process of

ardisinone E. Based on this retro synthetic analysis, the

synthetic process as summarized in Schemes 3 and 4 was

successfully adopted to prepare ardisinone E (15).

To explore the biological potential of compounds having

diarylundecanone skeleton, the synthesis of several new

diaryl undecanone derivatives, containing differently sub-

stituted aryl group in place of phloroglucinol and sub-

stituted phenyl group in place of 2-hydroxyphenyl group of

ardisinone E was attempted, based on the retrosynthtic

analysis adopted for ardisionone E.

Synthesis

Based on the disconnection approach summarized in

Schemes 1 and 2, the key intermediate 10 of ardisinone and

other diarylundecanones synthesis was prepared adopting

the Scheme 3. The intermediate methyl 6-al-hexanoate (3)

was obtained by cleaving the macrolactone ring of com-

mercially available ε-caprolactone in presence of H₂SO₄in

methanol. The aldehyde 3 was then reacted with suitably

substituted benzyltriphenylphosponium salts in presence of

strong base to get methyl 7-(substituted phenyl)hept-6-en-1-

oates (4a–e), which upon reduction with lithium aluminum

hydride followed by mild oxidation of the

reaction product with IBX yielded the aldehyde compounds

7-(substituted phenyl)heptan-1-al (6a–e, 65–72%). The

aldehyde compounds 6a–e were treated with

However, the terminal reaction intermediates, viz. dif-

ferently substituted arylundecanoic acid and phloroglucinol

substitute did not undergo Friedel Craft′s acylation as

expected probably because of the reduced electrophilicity of

phloroglucinol variant. Hence, a modiﬁed retro synthetic

Med Chem Res

Scheme 3 Synthesis of main

intermediate 10a–e. Reagents

and conditions: (i) H₂SO₄,

methanol; (ii) Jones reagent,

silicagel, dichloromethane; (iii)

Sodium hydride, Wittig salt,

THF; (iv) LAH, THF; (v) IBX,

DMSO; (vi)

O

i

O

ii

HO

O

2

3

O

1

R₁

iii

R₂

R₃

HO

iv

R₁

R₄

R₂

R₃

O

Triphenylcarbethoxy-

methylenephosphorane, THF;

(vii) Pd/CaCO₃, ethyl acetate

R₄

5a: R₁= OCH₃, R₂= R₃= R₄= H

5b: R₁= H, R₂= R₃= R₄= OCH₃

5c: R₁= R₂= H, R₃= R₄= OCH₃

5d: R₁= R₂= R₄= H, R₃= OCH₃

5e: R₁= R₂= R₃= R₄= H

4a: R₁= OCH₃, R₂= R₃= R₄= H

4b: R₁= H, R₂= R₃= R₄= OCH₃

4c: R₁= R₂= H, R₃= R₄= OCH₃

4d: R₁= R₂= R₄= H, R₃= OCH₃

4e: R₁= R₂= R₃= R₄= H

v

R₁

O

R₁

R₂

R₃

R₁

O

vi

R₂

R₃

EtO

6a-e

7a-e

R₄

R₁

R₂

R₃

vii

HO

O

iv

R₂

R₃

EtO

9a-e

R₄

8a-e

R₄

v

R₁

R₂

R₃

O

10a-e

R₄

triphenylcarbethoxymethylenephosphorane under modiﬁed

Wittig reaction conditions to obtain compounds 7a–e in

good yields (65–74%). Triphenylcarbethoxymethylenepho-

sphorane was prepared by adopting general methodology

reported by Denney et.al. (Denney and Ross 1962).

yield diarylundecanone 14 in 83% yield. Finally, the com-

pound 14 on vigorous demethylation using pyridinium

chloride afforded ardisinone E (15) in 35% yield.

For the synthesis of other diarylundecanones, the 9-

(substituted phenyl)-nonan-al compounds (10b–e) were

treated with substituted acetophenonephosphoranes 16a–d

via modiﬁed Wittig reaction to obtain 11-(substituted phe-

nyl)-1-(substituted phenyl)-undec-2-ene-1-ones (17a–p)

with yields in the range of 45–53%, which on catalytic

hydrogenation with 5% Pd/CaCO₃yielded the corre-

sponding 11-(substituted phenyl)-1-(substituted phenyl)-

undecan-1-one compounds 18a–p in 75–87% yields as

summarized Scheme 5.

The compounds 7a–e were subjected to catalytic reduc-

tion under hydrogen atmosphere with 5% Pd/CaCO₃to

obtain ethyl 9-(substituted phenyl)-nonanoates (8a–e) with

yields in the range of 85–90%, which on reduction with

LAH yielded 9-(substituted phenyl)nonan-ol compounds

(9a–e) in 80–85% yield. The compounds 9a–e were treated

with IBX in dichloromethane to obtain 9-(substituted phe-

nyl)nonan-al (10a–e) again in good yields (76–82%).

For the synthesis of ardisinone, the compound 10a was

treated with triphenylcarbethoxymethylenephosphorane

under modiﬁed Wittig reaction conditions as depicted in

Scheme 4, followed by base hydrolysis of the reaction

product to give 11-(2-methoxy-phenyl) undec-2-en-1-oic

acid (12) in 56% yield. The compound 12 was then treated

with tri-O-methyl phloroglucinol in presence of aluminum

chloride in dichloromethane at 0–5 °C to yield 11-(2-

methoxy-phenyl)-1-(2,4,6-trimethoxy phenyl)undec-2-en-1-

one (13, 65%). Compound 13 was subjected to catalytic

reduction with Pd/CaCO₃under hydrogen atmosphere to

Biological activities

All the compounds were tested to evaluate their potential

as antioxidant and to inhibit 5-lipoxygenase enzyme

and growth of brine shrimp. Ardisinone (15, 1-(2, 4, 6-

trihydroxyphenyl)-11-(2-hydroxyphenyl)-undecane-1-one,)

showed potent brine shrimp lethality with ED₅₀of 4.19 µg/mL.

The other diarylundecanone compounds 18c, 18e, 18f, 18j,

18k, 18l, 18m, 18o, and 18p showed moderate brine shrimp

lethality with ED₅₀values of 50.51, 63.14, 85.64, 70.38,

Med Chem Res

Scheme 4 Synthesis of

OCH₃

O

ardisinone E (15): Reagents and

conditions: (i) Triphenylcarbe-

thoxymethylenephosphorane,

THF; (ii) NaOH, MeOH; (iii)

SOCl₂, AlCl₃, dichloromethane,

tri-O-methylphloroglucinol;

(iv) Pd/CaCO₃, ethyl acetate;

(v) Pyridinium chloride

i

OEt

O

11

10a

13

ii

OCH₃

O

OCH₃

O

OCH₃

iii

OH

12

H₃CO

OCH₃

iv

OH

O

OH

OCH₃

O

OCH₃

v

15

HO

OH

14

H₃CO

OCH₃

44.67, 44.32, 60.09, 70.15, and 65.53 µg/mL respectively.

Podophyllotoxin (ED₅₀: 1.92 µg/mL) was used as positive

control.

Ardisinone E (15) showed moderate anti-oxidant activity

(IC₅₀: 56.64 µg/mL) in in vitro NBT anti-oxidant model. The

diarylundecanone analogs 18c, 18e, 18f, 18j, 18k, 18l, 18m,

and 18p showed relatively superior anti-oxidant activity

with IC₅₀values of 18.75, 12.28, 50.04, 18.35, 11.04, 12.05,

11.32, and 28.12 µg/mL, respectively. The positive control

gallic acid showed an IC₅₀value of 2.34 µg/mL.

methanol reagent followed by heating at 110 °C. Nitro blue

tetrazolium (NBT) was obtained from Sigma Chemicals

(USA). Brine shrimp (Artemiasalina Cysts) eggs were

obtained from Argent Chemical Laboratories, Redmond

(USA). The solvents and other chemicals used were of AR

grade and were procured from Qualigens Fine Chemicals,

Mumbai (India).

Methyl 6-hydroxyhexanoate (2)

The anti-inﬂammatory potential of ardisinone E (15) and

the diarylundecanone analogs 18a-p were evaluated in 5-

lipoxygenase enzyme inhibitory model. Compounds 18e,

18k, and 18m strongly inhibited 5-lipoxygenase with IC₅₀

values of 12.80, 15.23, and 15.23 µg/mL, respectively. The

compounds 18c, 18f, 18j, 18l, 18o, and 18p showed mod-

erate inhibitory activity with IC₅₀values of 62.10, 32.03,

35.54, 24.60, 43.35, and 53.51 µg/mL respectively. How-

ever, 15 showed inferior 5-lipoxygenase inhibition activity

with IC₅₀> 100 µg/mL. In comparison, the positive control

pure curcumin showed an IC₅₀value of 8.98 µg/mL.

ε-Caprolactone (30 g, 0.2631 mol) was dissolved in dry

methanol (150 mL), treated with 10 drops of conc.H₂SO₄,

and the reaction mixture was stirred for 2 h. After comple-

tion of reaction, the reaction mixture was poured into water

(500 mL) and extracted with chloroform (2 × 250 mL). The

combined organic layer was washed with brine solution,

dried over Na₂SO₄and concentrated under vacuum to yield

methyl 6-hydroxyhexanoate (32 g, 88%). ¹H NMR (CDCl₃,

400 MHz): δ 3.72 (3H, s, OCH₃), 3.53 (2H, t, J = 7.2 Hz,

H-6), 2.26 (2H, t, J = 7.6 Hz, H-2), 1.71–1.66 (2H, m, H-3),

1.54–1.49 (2H, m, H-5), 1.28–1.22 (2H, m, H-4); ¹³C NMR

(CDCl₃,100 MHz): δ 171.4 (C-1), 64.1 (C-6), 52.3 (OCH₃),

33.6 (C-2), 32.4 (C-5), 25.3 (C-4), 25.1 (C-3).

Experimental

The ¹H NMR spectra were recorded on Bruker Avance AV

400 MHz NMR spectrometer and ¹³C NMR spectra were

recorded on Bruker Avance AV 100 MHz NMR spectro-

meter. Mass studies were performed on LC-MS system

equipped with Agilent 1100 series LC/ MSD detector and

1100 series Agilent HPLC pump. Normal phase silica gel

(ACME, 100–200 mesh) was used for column chromato-

graphy. Silica gel pre-coated plates (AlugramSil G/UV254)

were used for thin layer chromatography. The plates were

eluted with a solvent system containing hexane/ethyl acetate

(9:1) and visualized by immersing the plate in sulfuric acid/

Methyl hex-6-al-1-oate (3)

Methyl 6-hydroxyhexanoate (2, 16 g, 0.1095 mol) was

dissolved in dichloromethane (450 mL) and treated with

Jones reagent (80 mL) adsorbed on silica gel (160 g) in

small portions under vigorous stirring. The reaction mixture

was then stirred for 3 h., the reaction mixture was ﬁltered

and the ﬁltrate was concentrated under vacuum. The crude

substance was puriﬁed further by column chromatography

(silica gel 100–200#, eluent: 15% ethyl acetate /hexane

mixtures) to yield methyl 6-al-hexanoate (11.9 g, 76%).

Med Chem Res

Scheme 5 Synthesis of

undecanone analogs (18a–p).

Reagents and conditions: (i)

THF; (ii) H₂-Pd/CaCO₃, ethyl

acetate

R₁

R₄

R₈

R₆

O

R₂

R₃

P(Ph)₃

O

R₇

R₅

10 b-e

16a-d

10b: R₁= H, R₂= R₃= R₄= OCH₃

10c: R₁= R₂= H, R₃= R₄= OCH₃

10d: R₁= R₂= R₄= H, R₃= OCH₃

10e: R₁= R₂= R₃= R₄= H

16a: R₅= R₆= R₇= R₈= H

16b: R₆= R₈= H, R₅= R₇= OCH₃

16c: R₅= R₈= H, R₆= R₇= OCH₃

16d: R₅= R₇= H, R₆= R₈= OCH₃

i

R₁

O

R₈

R₂

R₃

17a-p

ii

R₅

R₇

R₄

R₁

R₆

O

R₈

R₂

R₃

18a-p

R₅

R₇

R₄

R₆

18a: R₁= R₅= R₆= R₇= R₈= H; R₂= R₃= R₄= OCH₃

18b: R₁= R₂= R₅= R₆= R₇= R₈= H; R₃= R₄= OCH₃

18c: R₁= R₂= R₄= R₅= R₆= R₇= R₈= H; R₃= OCH₃

18d: R₁= R₂= R₃= R₄= R₅= R₆= R₇= R₈= H

18e: R₁= R₆= R₈= H; R₅= OH; R₂= R₃= R₄= R₇= OCH₃

18f: R₁= R₂= R₆= R₈= H; R₅= OH; R₃= R₄= R₇= OCH₃

18g: R₁= R₂= R₄= R₆= R₈= H; R₅= OH; R₃= R₇= OCH₃

18h: R₁= R₂= R₃= R₄= R₆= R₈= H; R₅= OH; R₇= OCH₃

18i: R₁= R₅= R₈= H; R₂= R₃= R₄= R₆= R₇= OCH₃

18j: R₁= R₂= R₅= R₈= H; R₃= R₄= R₆= R₇= OCH₃

18k: R₁= R₂= R₄= R₅= R₈= H; R₃= R₆= R₇= OCH₃

18l: R₁= R₂= R₃= R₄= R₅= R₈= H; R₆= R₇= OCH₃

18m:R₁= R₅= R₇= H; R₂= R₃= R₄= R₆= R₈= OCH₃

18n: R₁= R₂= R₅= R₇= H; R₃= R₄= R₆= R₈= OCH₃

18o: R₁= R₂= R₄= R₅= R₇= H; R₃= R₆= R₈= OCH₃

18p: R₁= R₂= R₃= R₄= R₅= R₇= H; R₆= R₈= OCH₃

¹H NMR (CDCl₃, 400 MHz): δ 9.72 (1H, t, J = 6.8 Hz,

H-6), 3.72 (3H, s, OCH₃), 2.43 (2H, t, J = 7.2 Hz, H-5),

2.24 (2H, t, J = 7.2 Hz, H-2), 1.72–1.69 (2H, m, H-3),

1.62–1.60 (2H, m, H-4); ¹³C NMR (CDCl₃, 100 MHz): δ

201.2 (C-6), 176.2 (C-1), 52.4 (OCH₃), 44.2 (C-5), 33.3 (C-

2), 24.8 (C-3), 22.3 (C-4).

with suitably substituted benzyltriphenyl-phosphonium

bromide (0.0765 mol) in small portions for 40 min. After

completion of the addition, the reaction mixture was stirred

for 30 min. Then Methyl hex-6-al-1-oate (3, 9.8 g, 0.06849

mol) dissolved in tetrahydrofuran (50 mL) was slowly

added dropwise to the reaction mixture. After completion of

addition, the reaction mixture was stirred for 3 h at room

temperature. After completion of reaction, the reaction

mixture was poured into ice cold water (800 mL) and the

mixture was acidiﬁed with 2N HCl and extracted with ethyl

acetate (2 × 300 mL). The combined organic layer was

washed with brine solution, dried over Na₂SO₄and

General procedure for 7-(substituted phenyl)-hept-6-enoic

acid methyl ester (4a–e)

NaH (6 g, 0.248 mol) was suspended in dry tetrahydrofuran

(250 mL). The mixture was cooled to 5 °C, and then treated

Med Chem Res

concentrated under vacuum. The crude mixture of the

reaction was puriﬁed by column chromatography (silica gel

100–200#, eluent: 5% ethyl acetate/hexane) to yield the

corresponding 7-(substituted phenyl)-hept-6-enoic acid

methyl ester (4a–e, 60–75%).

Hz, H-5), 1.66–1.62 (2H, m, H-3), 1.32–1.29 (2H, m, H-4);

¹³C NMR (CDCl₃, 100 MHz): δ 171.2 (C-1), 159.2 (C-4′),

128.8 (C-6), 127.3 (C-1′), 127.1 (C-2′,6′), 125.4 (C-7),

113.8 (C-3′, 5′), 55.1 (OCH₃), 51.8 (OCH₃), 33.2 (C-2),

33.0 (C-5), 29.4 (C-4), 25.4 (C-3); LC-MS: m/z 249.3 (M +

H)⁺, 271.2 (M + Na)⁺.

7-(2-methoxy-phenyl)-hept-6-enoic acid methyl ester (4a)

Oily substance, (11.38 g, 67%); ¹H NMR (CDCl₃, 400

MHz): δ 7.18 (1H, dd, J = 3.2, 8.4 Hz, H-6′), 7.06 (1H, td,

J = 3.2, 8.4 Hz, H-4′), 6.87 (1H, td, J = 3.6, 8.8 Hz, H-5′),

6.71 (1H, dd, J = 3.6, 8.4 Hz, H-3′), 6.62 (1H, d, J = 16.8

Hz, H-7), 5.82 (1H, td, J = 16.8, 7.2 Hz, H-6), 3.74 (3H, s,

OCH₃), 3.68 (3H, s, OCH₃), 2.21 (2H, t, J = 7.2 Hz, H-2),

1.93 (2H, t, J = 7.2 Hz, H-5), 1.68–1.65 (2H, m, H-3),

1.36–1.34 (2H, m, H-4); ¹³C NMR (CDCl₃, 100 MHz): δ

172.6 (C-1), 158.9 (C-2′), 128.6 (C-4′), 128.2 (C-6′), 126.9

(C-1′), 126.3 (C-7), 121.6 (C-6), 120.5 (C-5′), 115.2 (C-3′),

56.3 (OCH₃), 50.6 (OCH₃), 50.1 (C-5), 33.4 (C-2), 32.8 (C-

3), 25.6 (C-4); LC-MS: m/z 249.3 (M + H)⁺, 271.3 (M +

Na)⁺.

7-(Phenyl)-hept-6-enoic acid methyl ester (4e) Oily com-

pound, (10.15 g, 68%); ¹H NMR (CDCl₃, 400 MHz): δ 7.32

(2H, d, J = 8.4 Hz, H-2′, 6′), 7.25 (2H, t, J = 7.2 Hz, H-3′,

5′), 7.18 (1H, t, J = 7.6 Hz, H-4′), 6.38 (1H, d, J = 16.4 Hz,

H-7), 6.01 (1H, td, J = 16.4, 7.2 Hz, H-6), 3.63 (3H, s,

OCH₃), 2.22 (2H, t, J = 7.6 Hz, H-2), 1.92 (2H, t, J = 7.6

Hz, H-5), 1.68–1.62 (2H, m, H-3), 1.30–1.28 (2H, m, H-4);

¹³C NMR (CDCl₃, 100 MHz): δ 171.2 (C-1), 135.1 (C-1′),

128.8 (C-6), 128.5 (C-3′, 5′), 128.1 (C-4′), 126.2 (C-7),

125.6 (C-2′, 6′), 51.9 (OCH₃), 33.7 (C-2), 33.1 (C-5), 29.3

(C-4), 25.0 (C-3); LC-MS: m/z 217.4 (M−H)⁻.

General procedure for 7-(substituted phenyl)-heptan-1-ol

(5a–e)

7-(3,4,5-Trimethoxyphenyl)-hept-6-enoic acid methyl ester

(4b) Oily substance, (15.2 g, 72%); ¹H NMR (CDCl₃, 400

MHz): δ 6.88 (1H, d, J = 16.0 Hz, H-7), 6.21 (2H, s, H-2′,

6′), 6.01 (1H, td, J = 15.6, 6.4 Hz, H-6), 3.53 (3H, s,

OCH₃), 2.21 (2H, t, J = 7.6 Hz, H-2), 1.92 (2H, t, J = 7.6

Hz, H-5), 1.62–1.58 (2H, m, H-3), 1.31–1.29 (2H, m, H-4);

¹³C NMR (CDCl₃, 100 MHz): δ 171.2 (C-1), 150.5 (C-3′,

5′), 137.9 (C-4′), 129.4 (C-6), 129.1 (C-1′), 125.4 (C-7),

103.6 (C-2′, 6′), 56.2 (OCH₃), 56.1 (OCH₃), 51.6 (OCH₃),

33.5 (C-2), 33.1 (C-5), 29.5 (C-4), 25.3 (C-3); LC-MS: m/z

309.3 (M + H)⁺, 331.3 (M + Na)⁺.

Lithium aluminum hydride (3 g, 0.08108 mol) was sus-

pended in dry THF(100 mL), and then the mixture was

treated with a solution containing suitable methyl 7-(sub-

stituted phenyl)-hept-6-enoic acid methyl esters (4a–e,

0.0325 mol) dissolved in 25 ml dry THF drop wise with

stirring. After completion of reaction, mixture was poured

in to cold water (250 mL), acidiﬁed with 2N HCL and

extracted with chloroform (2 × 250 mL).The combined

organic layer was washed with brine solution, dried over

Na₂SO₄and concentrated under vacuum. The crude residue

was puriﬁed by column chromatography (eluent: 15–20%

ethyl acetate/hexane) to yield corresponding 7-(substituted

phenyl)-heptan-1-ol (5a–e, 75–87%).

7-(3,4-Dimethoxyphenyl)-hept-6-enoic acid methyl ester

(4c) Oily substance, (14.2 g, 75%); ¹H NMR (CDCl₃,

400 MHz): δ 6.72 (1H, dd, J = 8.0, 3.2 Hz, H-6′), 6.69 (1H,

d, J = 3.2 Hz, H-2′), 6.58 (1H, d, J = 8 Hz, H-5′), 6.39 (1H,

d, J = 16.4 Hz, H-7), 6.01 (1H, td, J = 15.6, 6.4 Hz, H-6),

3.52 (6H, s, OCH₃), 3.41 (3H, s, OCH₃), 2.22 (2H, t, J =

7.6 Hz, H-2), 1.90 (2H, t, J = 7.6 Hz, H-5), 1.62–1.56 (2H,

m, H-3), 1.30–1.28 (2H, m, H-4); ¹³C NMR (CDCl₃, 100

MHz): δ 171.2 (C-1), 149.1 (C-3′), 148.8 (C-4′), 128.8 (C-

6), 128.1 (C-1′), 125.4 (C-7), 119.3 (C-6′), 115.1 (C-5′),

111.2 (C-2′), 56.1 (OCH₃), 51.6 (OCH₃), 33.4 (C-2), 33.1

(C-5), 29.3 (C-4), 25.4 (C-3); LC-MS: m/z 279.2 (M + H)⁺,

301.3 (M + Na)⁺.

7-(2-Methoxyphenyl)-heptan-1-ol (5a) Oily compound.

(6.2 g, 87%); H NMR (CDCl₃, 400 MHz): δ 7.18 (1H, dd,

1

J = 3.2, 8.4 Hz, H-6′), 7.06 (1H, td, J = 3.2, 8.4 Hz, H-4′),

6.87 (1H, td, J = 3.6, 8.8 Hz, H-5′), 6.71 (1H, dd, J = 3.6,

8.4 Hz, H-3′), 3.74 (3H, s, OCH₃), 3.48 (2H, t, J = 6.8 Hz,

H-1), 2.49 (2H, t, J = 7.2 Hz, H-7), 2.02 (2H, t, J = 7.2 Hz,

H-2), 1.91 (2H, t, J = 7.2 Hz, H-5), 1.68–1.65 (4H, m, H-3,

6), 1.36–1.34 (2H, m, H-4); ¹³C NMR (CDCl₃, 100 MHz):

δ 158.4 (C-2′), 128.5 (C-4′), 128.2 (C-6′), 126.9 (C-1′),

126.3 (C-7), 121.6 (C-6), 120.5 (C-5′), 115.2 (C-3′), 64.3

(C-1), 56.3 (OCH₃), 50.1 (C-5), 33.4 (C-2), 32.8 (C-3), 25.6

(C-4); LC-MS: m/z 223.3 (M + H)⁺, 245.3 (M + Na)⁺.

7-(4-Methoxyphenyl)-hept-6-enoic acid methyl ester (4d)

Oily compound, (10.2 g, 60%); ¹H NMR (CDCl₃, 400

MHz): δ 7.09 (2 H, d, J = 7.6 Hz, H-2′, 6′), 6.65 (2H, d, J =

7.2 Hz, H-3′, 5′), 6.38 (1H, d, J = 16.4 Hz, H-7), 6.01 (1H,

td, J = 16.0, 6.4 Hz, H-6), 3.63 (3H, s, OCH₃), 3.58 (3H, s,

OCH₃), 2.21 (2H, t, J = 7.6 Hz, H-2), 1.91 (2H, t, J = 7.6

7-(3,4,5-Trimethoxyphenyl)-heptan-1-ol (5b) Oily com-

pound, (7.1 g, 7.8%); H NMR (CDCl₃, 400 MHz): δ 6.03

(2H, s, H-2′, 6′), 3.71 (9H, s, OCH₃), 3.53 (2H, t, J = 7.6

1

Med Chem Res

Hz, H-1), 2.46 (2H, t, J = 7.2 Hz, H-7), 2.0 (1H, s, OH),

1.61–1.59 (2H, m, H-6), 1.46–1.42 (2H, m, H-2), 1.28–1.22

(6H, m, H-3, 4, 5); ¹³C NMR (CDCl₃, 100 MHz): δ 149.2

(C-3′), 148.4 (C-5′), 140.6 (C-1′), 131.2 (C-4′), 108.3 (C-2′,

6′), 63.6 (C-1), 56.2 (OCH₃), 36.2 (C-7), 33.4 (C-2), 32.3

(C-6), 30.1 (C-4), 29.8 (C-5), 26.8 (C-3); LC-MS: m/z 283.3

(M + H)⁺, 305.3 (M + Na)⁺.

into water (200 mL).The mixture was ﬁltered, the ﬁlter bed

was washed with chloroform (200 mL). The ﬁltrate was

taken in to a separating funnel, separated the organic layer

and the aqueous layer was extracted with chloroform (200

mL). The combined organic layer was washed with water,

brine solution, dried over Na₂SO₄and concentrated under

vacuum. The crude residue was puriﬁed by column chro-

matography on silica gel (15% ethyl acetate/hexane) to get

corresponding 7-(substituted phenyl)-heptan-1-al (6a–e,

82–88%).

7-(3,4-Dimethoxyphenyl)-heptan-1-ol (5c) Oily com-

1

pound, (6.7 g, 82%); H NMR (CDCl₃, 400 MHz): δ 6.58

(1H, dd, J = 8.4, 3.6 Hz, H-6′), 6.51 (1H, d, J = 3.6 Hz, H-

2′), 6.48 (1H, d, J = 8.4 Hz, H-5′), 3.73 (6H, s, OCH₃), 3.53

(2H, t, J = 6.8 Hz, H-1), 2.45 (2H, t, J = 7.2 Hz, H-7), 2.06

(1H, s, OH), 1.63–1.61 (2H, m, H-6), 1.46–1.42 (2H, m, H-

2), 1.29–1.26 (6H, m, H-3, 4, 5); ¹³C NMR (CDCl₃, 100

MHz): δ 148.4 (C-3′), 144.8 (C-4′), 133.7 (C-1′), 122.4 (C-

6′), 116.9 (C-2′, 5′), 63.6 (C-1), 56.3 (OCH₃), 36.2 (C-7),

33.3 (C-2), 32.6 (C-6), 30.1 (C-4), 29.9 (C-5), 26.4 (C-3);

LC-MS: m/z 253.3 (M + H)⁺, 275.3 (M + Na)⁺, 291.4 (M

+ K)⁺.

7-(2-Methoxyphenyl)-heptan-1-al (6a) Oily compound,

(4.9 g, 83%.); ¹H NMR (CDCl₃, 400 MHz): δ 9.72 (1H, t, J

= 6.8 Hz, H-1), 7.02 (1H, dd, J = 3.6, 8.8 Hz, H-6′), 6.95

(1H, td, J = 3.2, 8.4 Hz, H-4′), 6.72 (1H, td, J = 3.6, 8.8 Hz,

H-5′), 6.68 (1H, dd, J = 3.2, 8.4 Hz, H-3′), 3.73 (3H, s,

OCH₃), 2.52 (2H, t, J = 7.2 Hz, H-2), 2.41 (2H, t, J = 7.2

Hz, H-7), 1.66–1.62(4H, m, H-3, 6), 1.28–1.22 (4H, m, H-

4, 5); ¹³C NMR (CDCl₃,100 MHz): δ 200.8 (C-1), 162.1

(C-2′), 129.6 (C-4′), 126.1 (C-6′), 125.3 (C-1′), 121.8 (C-

5′), 116.6 (C-2′), 56.3 (OCH₃), 43.8 (C-7), 32.8 (C-2), 29.9

(C-3), 29.7 (C-6), 25.6 (C-5), 22.8 (C-4); LC-MS: m/z 221.4

(M + H)⁺, 243.2 (M + Na)⁺.

7-(4-Methoxyphenyl)-heptan-1-ol (5d) Oily substance,

(5.4 g, 75%); ¹H NMR (CDCl₃, 400 MHz): δ 7.09 (2H, d, J

= 7.6 Hz, H-2′, 6′), 6.82 (2H, d, J = 7.2 Hz, H-3′, 5′), 3.73

(3H, s, OCH₃), 3.52 (2H, t, J = 7.2 Hz, H-1), 2.46 (2H, t, J

= 7.2 Hz, H-7), 2.1 (1H, s, OH), 1.63–1.61 (2H, m, H-6),

1.46–1.42 (2H, m, H-2), 1.29–1.26 (6H, m, H-3, 4, 5); ¹³C

NMR (CDCl₃, 100 MHz): δ 159.6 (C-4′), 132.7 (C-1′),

129.6 (C-2′, 6′), 114.8 (C-3′, 5′), 63.6 (C-1), 56.2 (OCH₃),

36.1 (C-7), 33.4 (C-2), 32.6 (C-6), 30.2 (C-4), 29.9 (C-5),

26.2 (C-3); LC-MS: m/z 223.3 (M + H)⁺, 245.4 (M +

Na)⁺, 261.4 (M + K)⁺.

7-(3,4,5-Trimethoxyphenyl)-heptan-1-al (6b) Oily com-

1

pound, (6.2 g, 82%); H NMR (CDCl₃, 400 MHz): δ 9.71

(1H, t, J = 7.2 Hz, H-1), 6.08 (2H, s, H-2′, 6′), 3.73 (9H, s,

OCH₃), 2.52 (2H, t, J = 7.2 Hz, H-7), 2.41 (2H, t, J = 7.2

Hz, H-2), 1.69–1.64 (4H, m, H-3, 6), 1.32–1.28 (4H, m, H-

4, 5); ¹³C NMR (CDCl₃, 100 MHz): δ 200.6 (C-1), 148.6

(C-3′, 5′), 134.6 (C-1′), 130.2 (C-4′), 106.3 (C-2′, 6′), 44.6

(C-2), 36.4 (C-7), 32.5 (C-6), 29.6 (C-4, 5), 22.5 (C-3); LC-

MS: m/z 281.3 (M + H)⁺, 303.4 (M + Na)⁺, 319.3

(M + K)⁺.

7-(Phenyl)-heptan-1-ol (5e) Oily compound, (5.0 g, 80 %);

¹H NMR (CDCl₃, 400 MHz): δ 7.24 (2H, d, J = 8.4 Hz, H-

3′, 5′), 7.14 (2 H, t, J = 7.2 Hz, H-2′, 6′), 7.09 (1H, t, J = 7.2

Hz, H-4′), 3.53 (2H, t, J = 7.2 Hz, H-1), 2.46 (2H, t, J = 7.2

Hz, H-7), 1.62–1.59 (2H, m, H-6), 1.46–1.42 (2H, m, H-2),

1.29–1.26 (6H, m, H-3, 4, 5); ¹³C NMR (CDCl₃, 100 MHz):

δ 139.2 (C-1′), 129.2 (C-2′, 3′, 5′, 6′) 126.2 (C-4′), 63.6 (C-

1), 36.0 (C-7), 33.4 (C-2), 32.6 (C-6), 30.3 (C-4), 29.9 (C-5),

26.3 (C-3); LC-MS: m/z 193.5 (M + H)⁺.

7-(3,4-Dimethoxyphenyl)-heptan-1-al (6c) Oily com-

1

pound, (6.0 g, 88%); H NMR (CDCl₃, 400 MHz): δ 9.72

(1H, t, J = 7.2 Hz, H-1), 6.58 (1H, td, J = 7.6, 3.2 Hz, H-6′),

6.52 (1H, d, J = 3.2 Hz, H-2′), 6.36 (1H, d, J = 7.6 Hz, H-

5′), 3.73 (6H, s, OCH₃), 2.52 (2H, t, J = 7.2 Hz, H-7), 2.42

(2H, t, J = 7.2 Hz, H-2), 1.69–1.64 (4H, m, H-3, 6),

1.32–1.29 (4H, m, H-4, 5); ¹³C NMR (CDCl₃, 100 MHz): δ

200.6 (C-1), 148.1 (C-3′), 145.6 (C-4′), 133.9 (C-1′), 122.6

(C-6′), 115.6 (C-2′, 5′), 56.2 (OCH₃), 44.6 (C-2), 36.4 (C-

7), 32.5 (C-6), 29.8 (C-4), 29.6 (C-5), 22.4 (C-3);

LC-MS: m/z 251.3 (M + H)⁺, 273.4 (M + Na)⁺, 289.3

(M + K)⁺.

General procedure for 7-(substituted phenyl)-hepan-1-al

(6a–e)

Suitable 7-(substituted phenyl)-heptan-1-ol (5a–e, 0.02727

mol) compound was dissolved in DMSO (60 mL) and to the

mixture was added IBX (7.1 g, 0.02727 mol) portion wise

for 20 min. After completion of addition, the reaction

mixture was stirred for 2 h. at room temperature. After

completion of reaction, the reaction mixture was poured

7-(4-Methoxyphenyl)-heptan-1-al (6d) Oily compound

(5.0 g, 85%); ¹H NMR (CDCl₃, 400 MHz): δ 9.72 (1H, t, J

= 7.2 Hz, H-1), 7.09 (2H, d, J = 7.2 Hz, H-2′, 6′), 6.82 (2H,

d, J = 7.2 Hz, H-3′, 5′), 3.72 (3H, s, OCH₃), 2.52 (2 H, t, J

= 7.2 Hz, H-7), 2.42 (2H, t, J = 7.2 Hz, H-2), 1.69–1.62

Med Chem Res

(4H, m, H-3, 6), 1.32–1.29 (4H, m, H-4, 5); ¹³C NMR

(CDCl₃, 100 MHz): δ 200.6 (C-1), 158.3 (C-4′), 132.6 (C-

1′), 129.6 (C-2′, 6′), 114.8 (C-3′, 5′), 54.6 (OCH₃), 44.6

(C-2), 36.4 (C-7), 32.5 (C-6), 29.8 (C-4), 29.6 (C-5), 22.4

(C-3); LC-MS: m/z 219.4 (M−H)⁻.

166 (C-1), 150.4 (C-3′, 5′), 149.3 (C-3), 136.1 (C-1′), 133.0

(C-4′), 121.2 (C-2), 105.8 (C-2′, 6′), 61.2 (OCH₂), 56.4

(OCH₃), 36.1 (C-9), 33.1 (C-4), 31.5 (C-8), 29.8 (C-6), 29.7

(C-7), 29.5 (C-5), 14.3 (CH₂CH₃); LC-MS: m/z 351.3 (M

+ H)⁺, 373.4 (M + Na)⁺.

7-(Phenyl)-heptane-1-al (6e) Oily substance (4.5 g, 87%);

¹H NMR (CDCl₃, 400 MHz): δ 9.74 (1H, s, H-1), 7.24 (2H,

d, J = 8.4 Hz, H-3′, 5′), 7.14 (2H, t, J = 7.6 Hz, H-2′, 6′),

7.06 (1H, t, J = 7.6 Hz, H-4′), 2.52 (2H, t, J = 7.2 Hz, H-7),

2.42 (2H, t, J = 7.2 Hz, H-2), 1.69–1.63 (4 H, m, H-3, 6),

1.32–1.28 (4 H, m, H-4, 5); ¹³C NMR (CDCl₃, 100 MHz): δ

200.6 (C-1), 140.2 (C-1′), 127.2 (C-2′, 3′, 5′, 6′), 126.8 (C-

4′), 44.6 (C-2), 36.4 (C-7), 32.9 (C-6), 29.9 (C-4), 29.6 (C-

5), 22.6 (C-3); LC-MS: m/z 191.3 (M + H)⁺.

9-(3,4-Dimethoxyphenyl)-nona-2-enoic acid ethyl ester

(7c) Oily substance, (4.8 g, 74%); ¹H NMR (CDCl₃,

400 MHz): δ 6.82 (1H, td, J = 16.8, 7.6 Hz, H-3), 6.60 (1H,

dd, J = 8.0, 3.2 Hz, H-5′), 6.53 (1H, d, J = 3.2 Hz, H-2′),

6.51 (1H, d, J = 8.0 Hz, H-6′), 5.81 (1H, t, J = 16.8 Hz, H-

2), 4.12 (2H, q, J = 6.4 Hz, OCH₂), 3.61 (6 H, s, OCH₃),

2.50 (2H, t, J = 7.6 Hz, H-9), 1.92 (2H, t, J = 7.6 Hz, H-4),

1.65–1.62 (2H, m, H-8), 1.34–1.32 (2H, m, H-5), 1.30 (3H,

t, J = 7.2 Hz, OCH₂CH₃), 1.29 (4H, s, H-6, 7); ¹³C NMR

(CDCl₃, 100 MHz): δ 166.1 (C-1), 149.5 (C-3), 149.4 (C-

3′), 147.1 (C-4′), 132.3 (C-1′), 121.8 (C-2), 115.3 (C-2′, 5′),

61.4 (OCH₂), 56.2 (OCH₃), 36.4 (C-9), 33.2 (C-4), 31.3 (C-

8), 29.8 (C-5), 29.7 (C-6), 29.3 (C-7), 14.5 (CH₂CH₃); LC-

MS: m/z 321.3 (M + H)⁺, 343.4 (M + Na)⁺.

General procedure for 9-(Substituted phenyl)-nona-2-enoic

acid ethyl ester (7a–e)

A mixture of suitable7-(substituted phenyl)-heptan-1-al

(6a–6e, 0.02045 mol), dry THF (50 mL) and ethyl triphe-

nylphosphorane (7.1 g, 0.02045 mol) was reﬂuxed for 4–5

h. After completion of reaction, the reaction mixture was

concentrated under vacuum. The crude mixture was puriﬁed

by column chromatography on silica gel (5–10% ethyl

acetate/hexane) to yield the corresponding 9-(substituted

phenyl)-nona-2-enoic acid ethyl ester (7a–7e, 65–74%).

9-(3-Methoxyphenyl)-nona-2-enoic acid ethyl ester (7d)

Oily substance (4.2 g, 72%); ¹H NMR (CDCl₃, 400 MHz): δ

7.05 (2H, d, J = 7.2 Hz, H-2′, 6′), 6.82 (1H, td, J = 16.8,

7.6 Hz, H-3), 6.74 (2H, d, J = 7.2 Hz, H-3′, 5′), 5.81 (1H, t,

J = 16.8 Hz, H-2), 4.19 (2H, q, J = 6.8 Hz, OCH₂), 3.71

(3H, s, OCH₃), 2.51 (2H, t, J = 8.0 Hz, H-9), 1.93 (2H, t, J

= 7.6 Hz, H-4), 1.64–1.62 (2H, m, H-8), 1.35–1.33 (2H, m,

H-5), 1.30 (3H, t, J = 7.2 Hz, CH₂CH₃), 1.29–1.27 (4H, m,

H-6, 7); ¹³C NMR (CDCl₃, 100 MHz): δ 166.1 (C-1), 157.9

(C-4′), 149.6 (C-3), 131.3 (C-1′), 129.2 (C-2′, 6′), 121.3 (C-

2), 114.6 (C-3′, 5′), 61.4 (OCH₂), 55.8 (OCH₃), 36.2 (C-9),

33.3 (C-4), 31.4 (C-8), 29.8 (C-6), 29.7 (C-5), 29.3 (C-7),

14.2 (CH₂–CH₃); LC-MS: m/z 291.3 (M + H)⁺, 313.4

(M + Na)⁺.

9-(2-MethoxyPhenyl)-nona-2-enoic acid ethyl ester (7a)

1

Oily substance, (4.1 g, 69%); H NMR (CDCl₃, 400 MHz):

δ 7.04 (1H, dd, J = 3.6, 8.8 Hz, H-6′), 6.89 (1H, td, J =

17.2, 7.6 Hz, H-3), 6.85 (1H, td, J = 3.2, 8.4 Hz, H-4′), 6.71

(1H, td, J = 3.6, 8.8 Hz, H-5′), 6.66 (1H, dd, J = 3.2, 8.4

Hz, H-3′), 5.81 (1H, t, J = 17.2 Hz, H-2), 4.12 (2H, q, J =

6.8 Hz, OCH₂), 3.73 (3H, s, OCH₃), 2.52 (2H, t, J = 7.6 Hz,

H-9), 1.93 (2H, t, J = 7.2 Hz, H-4), 1.68–1.64 (2H, m, H-8),

1.35–1.32 (2H, m, H-5), 1.31 (3H, t, J = 6.4 Hz, CH₂–

CH₃), 1.29–1.22 (4H, m, H-6, 7); ¹³C NMR (CDCl₃, 100

MHz): δ 165.3 (C-1), 161.6 (C-2′), 129.4 (C-4′), 126.8 (C-

6′), 126.1 (C-3), 121.1 (C-1′), 120.8 (C-2), 118.3 (C-5′),

114.6 (C-3′), 59.6 (OCH₂), 56.2 (OCH₃), 32.8 (C-9), 30.5

(C-4), 30.1 (C-8), 25.6 (C-5, 6, 7), 13.8 (CH₂–CH₃); LC-

MS: m/z 291.3 (M + H)⁺, 313.4 (M + Na)⁺.

9-(Phenyl)-nona-2-enoic acid ethyl ester (7e) Oily com-

1

pound, (3.9 g, 73%); H NMR (CDCl₃, 400 MHz): δ 7.21

(2H, d, J = 8.4 Hz, H-3′, 5′), 7.16 (2H, t, J = 8.0 Hz, H-2′,

6′), 7.06 (1H, t, J = 7.6 Hz, H-4′), 6.82 (1H, td, J = 16.8,

7.6 Hz, H-3), 5.81 (1H, t, J = 16.8 Hz, H-2), 4.19 (2H, q, J

= 7.2 Hz, OCH₂), 2.55 (2H, t, J = 7.6 Hz, H-9), 1.95 (2H, t,

J = 7.6 Hz, H-4), 1.66–1.62 (2H, m, H-8), 1.35–1.33 (2H,

m, H-5), 1.30 (3H, q, J = 7.2 Hz, CH₂CH₃), 1.29–1.26 (4H,

m, H-6, 7); ¹³C NMR (CDCl₃, 100 MHz): δ 166.1 (C-1),

149.7 (C-3), 138.6 (C-1′), 128.6 (C-2′, 6′), 128.2 (C-3′, 5′),

126.3 (C-4′), 121.9 (C-2), 61.4 (CH₂), 36.2 (C-9), 33.3 (C-

4), 31.4 (C-8), 29.8 (C-6), 29.6 (C-5), 29.4 (C-7), 14.2

(CH₂–CH₃); LC-MS: m/z 261.3 (M + H)⁺, 283.5 (M +

Na)⁺.

9-(3,4,5-Trimethoxyphenyl)-nona-2-enoic acid ethyl ester

1

(7b) Oily substance, (4.6 g, 65%); H NMR (CDCl₃, 400

MHz): δ 6.82 (1H, td, J = 16.8, 7.6 Hz, H-3), 6.02 (2H, s,

H-2′, 6′), 5.81 (1H, t, J = 16.8 Hz, H-2), 4.12 (2H, q, J =

6.4 Hz, OCH₂), 3.65 (9H, s, OCH₃), 2.51 (2H, t, J = 7.2 Hz,

H-9), 1.92 (2H, t, J = 7.6 Hz, H-4), 1.62–1.66 (2H, m, H-8),

1.35v1.32 (2H, m, H-5), 1.30 (3H, t, J = 7.2 Hz, CH₂CH₃),

1.29–1.27 (4H, m, H-6, 7); ¹³C NMR (CDCl₃, 100 MHz): δ

Med Chem Res

General procedure for 9-(substituted phenyl)-nonanoic acid

ethyl ester (8a–e)

61.4 (OCH₂), 56.3 (OCH₃), 36.2 (C-9), 33.3 (C-2), 31.9 (C-

8), 29.7 (C-6), 29.4 (C-5), 29.3 (C-7), 29.1 (C-4), 25.3 (C-

3), 14.2 (OCH₂CH₃); LC-MS: m/z 323.3 (M + H)⁺, 345.4

(M + Na)⁺.

A mixture of suitable 9-(substituted phenyl)-nona-2-enoic

acid ethyl esters (7a–e, 0.01 mol), ethyl acetate (40 mL) and

5% palladium on CaCO₃(10 mg) was taken in a RB ﬂask

and contents were vigorously stirred under H₂atmosphere

for 2 h. After completion of reaction, the reaction mixture

was ﬁltered on celite, washed with ethyl acetate and the

ﬁltrate was concentrated under vacuum to obtain the cor-

responding 9-(substituted phenyl)-nonanoic acid ethyl ester

(8a–e, 85–90%).

9-(4-Methoxyphenyl)-nonanoic acid ethyl ester (8d) Oily

1

compound, (2.5 g, 85%); H NMR (CDCl₃, 400 MHz): δ

7.05 (2H, d, J = 7.6 Hz, H-2′, 6′), 6.72 (2H, d, J = 7.2 Hz,

H-3′, 5′), 4.12 (2H, q, J = 6.8 Hz, OCH₂), 3.63 (3H, s,

OCH₃), 2.55 (2H, t, J = 6.8 Hz, H-9), 2.26 (2H, t, J = 7.2

Hz, H-2), 1.71–1.68 (2H, m, H-3), 1.65–1.62 (2H, m, H-8),

1.30 (3H, t, J = 6.8 Hz, OCH₂CH₃), 1.29–1.26 (8H, m, H-4,

5, 6, 7); ¹³C NMR (CDCl₃, 100 MHz): δ 173.2 (C-1), 157.8

(C-4′), 131.9 (C-1′), 129.1 (C-2′, 6′), 114.2 (C-3′, 5′), 61.4

(OCH₂), 55.8 (OCH₃), 36.0 (C-9), 33.3 (C-2), 31.7 (C-8),

29.9 (C-6), 29.7 (C-5), 29.4 (C-7), 29.1 (C-4), 25.1 (C-3),

14.2 (OCH₂CH₃); LC-MS: m/z 293.4 (M + H)⁺, 315.3

(M + Na)⁺.

9-(2-Methoxyphenyl)-nonanoic acid ethyl ester (8a) Oily

1

substance, (3.6 g, 90%); H NMR (CDCl₃, 400 MHz): δ

7.04 (1H, dd, J = 3.6, 8.8 Hz, H-6′), 6.85 (1H, td, J = 3.2,

8.4 Hz, H-4′), 6.71 (1H, td, J = 3.6, 8.8 Hz, H-5′), 6.66 (1H,

dd, J = 3.2, 8.4 Hz, H-3′), 4.18 (2H, q, J = 6.8 Hz, OCH₂),

3.82 (3H, s, OCH₃), 3.73 (3H, s, OCH₃), 2.51 (2H, t, J =

7.6 Hz, H-9), 2.22 (2H, t, J = 7.2 Hz, H-2), 1.68–1.66 (2H,

m, H-3), 1.63–1.61 (2H, m, H-8), 1.31 (3H, t, J = 6.8 Hz,

OCH₂CH₃), 1.29–1.23 (8H, m, H-4, 5, 6, 7); ¹³C NMR

(CDCl₃, 100 MHz): δ 172.1 (C-1), 162.1 (C-2′), 130.3 (C-

6′), 127.6 (C-4′), 125.1 (C-1′), 121.6 (C-5′), 114.2 (C-3′),

59.6 (OCH₂), 56.1 (OCH₃), 33.8 (C-2), 32.8 (C-8), 30.4 (C-

6), 29.9 (C-7), 29.7 (C-4), 25.6 (C-9), 25.4 (C-3), 13.8

(OCH₂CH₃); LC-MS: m/z 293.3 (M + H)⁺, 315.3 (M +

Na)⁺.

9-(Phenyl)-nonanoic acid ethyl ester (8e) Oily substance,

(2.3 g, 87%); ¹H NMR (CDCl₃, 400 MHz): δ 7.21 (2H, d, J

= 7.6 Hz, H-3′, 5′), 7.12 (2H, t, J = 7.2 Hz, H-2′, 6′), 7.01

(1H, t, J = 7.6 Hz, H-4′), 4.12 (2H, q, J = 6.8 Hz, CH₂),

2.55 (2H, t, J = 6.8 Hz, H-9), 2.25 (2H, t, J = 7.2 Hz, H-2),

1.72–1.68 (2H, m, H-3), 1.66–162 (2H, m, H-8), 1.29–1.24

(8H, m, H-4, 5, 6, 7); ¹³C NMR (CDCl₃, 100 MHz): δ 173.2

(C-1), 138.6 (C-1′), 128.7 (C-2′, 6′), 128.0 (C-3′, 5′), 126.2

(C-4′), 61.4 (OCH₂), 36.3 (C-9), 33.3 (C-2), 31.9 (C-8),

29.9 (C-6), 29.4 (C-5), 29.3 (C-7), 29.1 (C-4), 25.5 (C-3),

14.2 (OCH₂–CH₃); LC-MS: m/z 263.3 (M + H)⁺, 285.3

(M + Na)⁺.

9-(3,4,5-Trimethoxyphenyl)-nonanoic acid ethyl ester

1

(8b) Oily compound, (3.0 g, 90%); H NMR (d₆-DMSO,

400 MHz): δ 6.08 (2H, s, H-2′, 6′), 4.10 (2H, q, J = 6.8 Hz,

OCH₂), 3.63 (9H, s, OCH₃), 2.55 (2H, t, J = 6.8 Hz, H-9),

2.25 (2H, t, J = 7.2 Hz, H-2), 1.72–1.68 (2H, m, H-3),

1.65–1.62 (2H, m, H-8), 1.30 (3H, t, J = 6.8 Hz,

OCH₂CH₃), 1.29–1.28 (8H, m, H-4, 5, 6, 7); ¹³C NMR (d₆-

DMSO, 100 MHz): δ 173.2 (C-1), 150.4 (C-3′, 5′), 136.4

(C-1′), 133.5 (C-4′), 105.9 (C-2′, 6′), 61.4 (OCH₂), 58.4

(OCH₃), 55.2 (OCH₃), 36.9 (C-9), 33.7 (C-8), 31.3 (C-2),

29.9 (C-6), 29.7 (C-5), 29.4 (C-4), 29.1 (C-7), 25.2 (C-3),

14.1 (OCH₂–CH3); LC-MS: m/z 353.3 (M + H)⁺, 375.3

(M + Na)⁺, 391.4 (M + K)⁺.

General procedure for 9-(substituted phenyl)-nonane-1-ol

(9a–e)

Lithium aluminum hydride (1.1 g, 0.0299 mol) was sus-

pended in dry THF (20 mL) and treated with a solution of

suitable 9-(substituted phenyl)-nonanoic acid ethyl esters

(8a–e 0.01198 mol) in THF (5 mL) was added slowly drop

wise for 15 min. Then the reaction mixture was stirred for

2 h. After completion of reaction, the reaction mixture was

poured into water (100 mL), acidiﬁed with 2N HCl and

extracted with chloroform (2 × 250 mL). The combined

organic layer was washed with brine solution, dried over

Na₂SO₄and concentrated under vacuum. The crude residue

was puriﬁed by column chromatography on silica gel (20 %

ethyl acetate/hexane) to yield the corresponding 9-(sub-

stituted phenyl)-nonan-1-ol (9a–e, 80–85%).

9-(3,4-Dimethoxyphenyl)-nonanoic acid ethyl ester (8c)

Oily compound, (2.8 g, 89%); ¹H NMR (CDCl₃, 400 MHz):

δ 6.61 (1H, dd, J = 8.4, 3.6 Hz, H-6′), 6.55 (1H, d, J = 3.6

Hz, H-2′), 6.51 (1H, d, J = 8.4 Hz, H-5′), 4.12 (2H, q, J =

6.8 Hz, OCH₂), 3.63 (6H, s, OCH₃), 2.55 (2H, t, J = 6.8 Hz,

H-9), 2.25 (2H, t, J = 7.2 Hz, H-2), 1.72–1.69 (2H, m, H-3),

1.65–1.62 (2H, m, H-8), 1.30 (3H, t, J = 7.2 Hz,

OCH₂CH₃), 1.29–1.25 (8H, m, H-4, 5, 6, 7); ¹³C NMR

(CDCl₃, 100 MHz): δ 173.2 (C-1), 149.6 (C-3′), 147.2 (C-

4′), 132.6 (C-1′), 121.1 (C-6′), 115.5 (C-2′), 113.3 (C-5′),

9-(2-Methoxyphenyl)-nonan-1-ol (9a) Oily compound,

(2.51 g, 83%); ¹H NMR (CDCl₃, 400 MHz): δ 7.04 (1H, dd,

J = 3.6, 8.8 Hz, H-6′), 6.85 (1H, td, J = 3.2, 8.4 Hz, H-4′),

Med Chem Res

6.71 (1H, td, J = 3.6, 8.8 Hz, H-5′), 6.66 (1H, dd, J = 3.2,

8.4 Hz, H-3′), 3.73 (3H, s, OCH₃), 3.52 (2H, t, J = 7.2 Hz,

H-1), 2.51 (2H, t, J = 7.6 Hz, H-9), 1.68–1.63 (2H, m, H-8),

1.46–1.42 (2H, m, H-2), 1.26–1.21 (10H, m, H-3, 4, 5, 6,

7); ¹³C NMR (CDCl₃, 100 MHz): δ 162.1 (C-2′), 130.4 (C-

6′), 127.3 (C-4′), 126.1 (C-1′), 121.8 (C-5′), 114.6 (C-3′),

64.2 (C-1), 56.3 (OCH₃), 33.4 (C-2), 32.8 (C-8), 30.4 (C-4,

5, 6), 29.8 (C-7), 26.4 (C-3), 25.9 (C-9); LC-MS: m/z 241.4

(M−H)⁻.

9), 32.3 (C-2), 30.6 (C-8), 29.7 (C-4, 5, 6), 29.3 (C-7), 25.7

(C-3); LC-MS: m/z 221.3 (M + H)⁺, 243.4 (M + Na)⁺.

General procedure for 9-(substituted phenyl)-nonane-1-al

(10a–e)

To a mixture of 9-(substituted phenyl)-nonan-1-ol com-

pounds (9a–e, 0.01 mol) in DMSO (20 mL) in a 100 mL R.

B ﬂask was added IBX (0.01 mol) slowly portion wise and

the reaction mixture was then stirred for 3 h. After com-

pletion of reaction, the reaction mixture was poured into

water (100 mL) and chloroform (100 mL).The mixture was

kept under stirring for 10 min and then ﬁltered, and the ﬁlter

bed washed with chloroform (100 mL). The organic layer

was separated. The aqueous layer was extracted with

chloroform (100 mL) and the combined the organic layer

was washed with water, brine solution, dried over Na₂SO₄

and concentrated under vacuum. The crude residue was

puriﬁed by column chromatography (15% ethyl acetate/

hexane eluent) to obtain the corresponding 9-(substituted

phenyl)-nonan-1-al (10a–10e, 76–82%).

9-(3,4,5-Trimethoxyphenyl)-nonan-1-ol (9b) Oily com-

1

pound, (3.2 g, 85%); H NMR (CDCl₃, 400 MHz): δ 6.06

(2H, s, H-2′, 6′), 3.63 (9H, s, OCH₃), 3.52 (2H, d, J = 7.2

Hz, H-1), 2.55 (2H, t, J = 6.8 Hz, H-9), 2.06 (1H, t, J = 4.8

Hz, OH), 1.65–1.62 (2H, m, H-8), 1.48–1.45 (2H, m, H-2),

1.29–1.26 (10H, m, H-3, 4, 5, 6, 7); ¹³C NMR (CDCl₃, 100

MHz): δ 150.6 (C-3′, 5′), 136.0 (C-1′), 133.4 (C-4′), 105.9

(C-2′, 6′), 62.5 (C-1), 58.5 (OCH₃), 58.2 (OCH₃), 36.3 (C-

9), 32.3 (C-8), 31.6 (C-2), 29.7 (C-4, 5, 6), 29.4 (C-7), 25.6

(C-9); LC-MS: m/z 311.3 (M + H)⁺, 333.4 (M + Na)⁺.

9-(3,4-Dimethoxyphenyl)-nonan-1-ol (9c) Oily substance,

1

(2.7 g, 80%); H NMR (CDCl₃, 400 MHz): δ 6.61 (1H, dd,

9-(2-Methoxyphenyl)-nonan-1-al (10a) Oily substance,

(2.0 g, 81%); H NMR (CDCl₃, 400 MHz): δ 9.72 (1H, s,

J = 8.4, 3.6 Hz, H-6′), 6.55 (1H, d, J = 3.2 Hz, H-2′), 6.51

(1H, d, J = 8.4 Hz, H-5′), 3.73 (6H, s, OCH₃), 3.52 (2H, t, J

= 6.8 Hz, H-1), 2.55 (2H, t, J = 7.2 Hz, H-9), 2.1 (1H, t, J

= 6.8 Hz, OH), 1.65–1.62 (2H, m, H-8), 1.46–1.42 (2H, m,

H-2), 1.29–1.26 (10H, m, H-3, 4, 5, 6, 7); ¹³C NMR

(CDCl₃, 100 MHz): δ 149.6 (C-3′), 147.6 (C-4′), 132.5 (C-

1′), 121.0 (C-6′), 115.2 (C-2′), 113.9 (C-5′), 62.5 (C-1), 58.5

(OCH₃), 36.3 (C-9), 32.3 (C-2), 31.6 (C-8), 29.7 (C-4, 5, 6),

29.3 (C-7), 25.7 (C-3); LC-MS: m/z 281.3 (M + H)⁺, 303.4

(M + Na)⁺.

1

H-1) 7.04 (1H, dd, J = 3.6, 8.8 Hz, H-6′), 6.85 (1H, td, J =

3.2, 8.4 Hz, H-4′), 6.71 (1H, td, J = 3.6, 8.8 Hz, H-5′), 6.66

(1H, dd, J = 3.2, 8.4 Hz, H-3′), 3.73 (3H, s, OCH₃), 2.51

(2H, t, J = 7.2 Hz, H-9), 2.46 (2H, t, J = 7.6 Hz, H-2),

1.68–1.66 (4H, m, H-3, 8), 1.29–1.23 (8H, m, H-4, 5, 6, 7);

¹³C NMR (CDCl₃, 100 MHz): δ 201.6 (C-1), 162.6 (C-2′),

130.2 (C-6′), 126.7 (C-4′), 125.6 (C-1′), 121.1 (C-5′), 114.6

(C-3′), 56.4 (OCH₃), 44.2 (C-2), 32.8 (C-8), 30.4 (C-6),

30.0 (C-5), 29.9 (C-7), 29.8 (C-4), 25.9 (C-9), 22.6 (C-3);

LC-MS: m/z 249.2 (M + H)⁺, 271.3 (M + Na)⁺.

9-(4-Methoxyphenyl)-nonan-1-ol (9d) Oily substance,

(2.4 g, 81%); ¹H NMR (CDCl₃, 400 MHz): δ 7.05 (2H, d, J

= 8.4 Hz, H-2′, 6′), 6.72 (2H, d, J = 7.6 Hz, H-3′, 5′), 3.73

(3H, s, OCH₃), 5.52 (2H, t, J = 7.2 Hz), 2.51 (2H, t, J = 6.8

Hz, H-9), 2.1 (1H, t, J = 6.4 Hz, OH), 1.65–1.63 (2H, m, H-

8), 1.46–1.42 (2H, m, H-2), 1.29–1.22 (10H, m, H-3, 4, 5,

6, 7); ¹³C NMR (d₆-DMSO, 100 MHz): δ 157.8 (C-4′),

131.9 (C-1′), 129.0 (C-2′, 6′), 114.9 (C-3′, 5′), 62.5 (C-1),

58.5 (OCH₃), 36.3 (C-9), 32.3 (C-8), 31.2 (C-2), 29.7 (C-4,

5, 6), 29.3 (C-7), 25.6 (C-3); LC-MS: m/z 249.5 (M−H)⁻.

9-(3,4,5-Trimethoxyphenyl)-nonan-1-al (10b) Oily com-

1

pound, (2.3 g, 76%); H NMR (CDCl₃, 400 MHz): δ 9.71

(1H, s, H-1), 6.06 (2H, s, H-2′, 6′), 3.65 (9H, s, OCH₃), 2.55

(2H, t, J = 7.6 Hz, H-9), 2.40 (2H, t, J = 7.2 Hz, H-2),

1.66–1.62 (4H, m, H-3, 8), 1.29–1.22 (8H, m, H-4, 5, 6, 7);

¹³C NMR (CDCl₃, 100 MHz): δ 202.6 (C-1), 150.1 (C-3′,

5′), 136.6 (C-1′), 133.5 (C-4′), 105.5 (C-2′, 6′), 58.5

(OCH₃), 58.3 (OCH₃), 43.6 (C-2), 36.5 (C-9), 31.4 (C-8),

29.6 (C-5), 29.4 (C-6), 29.3 (C-4), 22.2 (C-3); LC-MS: m/z

309.3 (M + H)⁺, 331.4 (M + Na)⁺.

9-(Phenyl)-nonan-1-ol (9e) Oily compound, (2.2 g, 84 %);

¹H NMR (CDCl₃, 400 MHz): δ 7.21 (2H, d, J = 7.6 Hz, H-

2′, 6′), 7.12 (2H, t, J = 7.6 Hz, H-3′, 5′), 7.08 (1H, t, J = 7.2

Hz, H-4′), 3.52 (2H, t, J = 8.4 Hz, H-1), 2.55 (2H, t, J = 8.0

Hz, H-9), 2.02 (1H, t, J = 5.2 Hz, OH), 1.65–1.62 (2H, m,

H-8), 1.48–1.44 (2H, m, H-2), 1.29–1.21 (10H, m, H-3, 4,

5, 6, 7); ¹³C NMR (CDCl₃, 100 MHz): δ 138.6 (C-1′), 128.7

(C-2′, 6′), 128.2 (C-3′, 5′), 126.0 (C-4′), 62.5 (C-1), 36.3 (C-

9-(3,4-Dimethoxyphenyl)-nonan-1-al (10c) Oily com-

1

pound, (2.3 g, 82 %); H NMR (CDCl₃, 400 MHz): δ 9.71

(1H, s, H-1), 6.64 (1H, dd, J = 8.0, 3.6 Hz, H-6′), 6.59 (1H,

d, J = 3.6 Hz, H-2′), 6.51 (1H, d, J = 8.0 Hz, H-5′), 3.63

(6H, s, OCH₃), 2.55 (2H, t, J = 6.8 Hz, H-9), 2.40 (2H, t,

J = 7.2 Hz, H-2), 1.66–1.61 (4H, m, H-3, 8), 1.29–1.23

Med Chem Res

(8H, m, H-4, 5, 6, 7); ¹³C NMR (d₆-DMSO, 100 MHz): δ

202.6 (C-1), 149.6 (C-3′), 147.6 (C-4′), 132.5 (C-1′), 121.0

(C-6′), 115.2 (C-5′), 113.1 (C-2′), 58.3 (OCH₃), 43.6 (C-2),

36.5 (C-9), 31.3 (C-8), 29.7 (C-5, 6), 29.3 (C-7), 29.2 (C-4),

22.3 (C-3); LC-MS: m/z 279.3 (M + H)⁺, 301.4 (M + Na)⁺,

317.4 (M + K)⁺.

25.6 (C-11); LC-MS: m/z 319.3 (M + H)⁺, 341.3 (M +

Na)⁺.

11-(2-Methoxyphenyl)-undec-2-enoic acid (12)

A solution of 11-(2-methoxy-Phenyl)-undec-2-enoic acid

ethyl ester (11, 2 g, 0.006289 mol) in methanol (10 mL) was

treated with 8 N KOH solution (5 mL) slowly and drop wise

for 10 min. Then, the reaction mixture was stirred at room

temperature for 1 h. After completion of reaction, the

reaction mixture was poured into water (50 mL), acidiﬁed

with 2N HCl and extracted with ethyl acetate (2 × 200 mL).

The organic layer was washed with brine solution, dried

over Na₂SO₄and concentrated. The residue was puriﬁed by

column chromatography on silica gel (10 % ethyl acetate/

hexane) to obtain 11-(2-methoxy Phenyl)-undec-2-enoic

acid (12, 1.51 g, 82 %). ¹H NMR (CDCl₃, 400 MHz): δ 11.2

(1H, s, OH), 7.16 (1H, t, J = 17.2 Hz, H-3), 7.04 (1H, dd, J

= 3.2, 7.6 Hz, H-6′), 6.97 (1H, td, J = 8.0, 3.6 Hz, H-4′),

6.79 (1H, td, J = 8.4, 3.6 Hz, H-5′), 6.74 (1H, dd, J = 7.6,

3.2 Hz, H-3′), 6.02 (1H, d, J = 17.2 Hz, H-2), 3.72 (3H, s,

OCH₃), 2.52 (2H, t, J = 7.2 Hz, H-11), 1.93 (2H, t, J = 7.2

Hz, H-4), 1.66–1.64 (2H, m, H-10), 1.36–1.32 (2H, m, H-

5), 1.29–1.23 (8H, m, H-6, 7, 8, 9); ¹³C NMR (CDCl₃, 100

MHz): δ 171.2 (C-1), 159.2 (C-2′), 154.6 (C-3), 129.3 (C-

6′), 127.2 (C-4′), 125.2 (C-1′), 120.9 (C-5′), 120.1 (C-2),

116.1 (C-3′), 33.2 (C-4,10), 31.8 (C-6,7,8), 29.8 (C-5), 29.7

(C-9), 26.2 (C-11); LC-MS: m/z 305.4 (M−H)⁻.

9-(4-Methoxyphenyl)-nonan-1-al (10d) Oily substance,

1

(1.9 g, 78 %); H NMR (CDCl₃, 400 MHz): δ 9.71 (1H, s,

H-1), 7.01 (2H, d, J = 8.0 Hz, H-2′, 6′), 6.69 (2H, d, J = 7.6

Hz, H-3′, 5′), 3.63 (3H, s, OCH₃), 2.55 (2H, t, J = 7.2 Hz,

H-9), 2.40 (2H, t, J = 7.2 Hz, H-2), 1.66–1.59 (4H, m, H-3,

8), 1.28–1.24 (8H, m, H-4, 5, 6, 7); ¹³C NMR (CDCl₃, 100

MHz): δ 202.6 (C-1), 157.6 (C-4′), 131.9 (C-1′), 129.1 (C-

2′, 6′), 114.2 (C-3′, 5′), 58.5 (OCH₃), 43.6 (C-2), 36.3 (C-9),

31.0 (C-8), 29.7 (C-5, 6), 29.4 (C-7), 29.3 (C-4), 22.4 (C-3);

LC-MS: m/z 249.2 (M + H)⁺, 271.4 (M + Na)⁺.

9-(Phenyl)-nonan-1-al (10e) Oily compound, (1.7 g, 80 %);

¹H NMR (CDCl₃, 400 MHz): δ 9.72 (1H, s, H-1), 7.21 (2H,

d, J = 7.6 Hz, H-2′, 6′), 7.12 (2H, t, J = 7.2 Hz, H-3′, 5′), 7.01

(1H, t, J = 7.6 Hz, H-4′), 2.55 (2H, t, J = 6.8 Hz, H-9), 2.42

(2H, t, J = 7.2 Hz, H-2), 1.67–1.62 (4H, m, H-3, 8),

1.26–1.22 (8H, m, H-4, 5, 6, 7); ¹³C NMR (CDCl₃, 100

MHz): δ 202.6 (C-1), 138.1 (C-1′), 128.7 (C-2′, 6′), 128.4 (C-

3′, 5′), 126.2 (C-4′), 43.6 (C-2), 36.3 (C-9), 31.3 (C-8), 29.7

(C-5,6), 29.3 (C-7), 29.2 (C-4), 22.4 (C-3); LC-MS: m/z 217.5

(M−H)⁻.

11-(2-Methoxyphenyl)-1-(2,4,6-trimethoxyphenyl)-undec-2-

11-(2-Methoxyphenyl)-undec-2-en-1-oic acid ethyl ester

en-1-one (13)

(11)

A mixture of 11-(2- methoxyphenyl)-undec-2-enoic acid

(12, 600 mg, 2.089 mmol) and thionyl chloride (0.5 mL,

4.137 mmol) was reﬂuxed for 1 h. Then, excess of thionyl

chloride was removed by heating under high vacuum to

obtain the acid chloride. A mixture of aluminum chloride

(340 mg, 2.55 mmol) and dichloromethane (5 mL) was

cooled to 0-5 °C, and then treated with a solution of tri-

methoxyphloroglucinol in methylenedichloride (5 mL) drop

wise. After completion of addition, the reaction mixture was

stirred for 30 min, and then treated drop wise with a solution

of previously prepared dried acid chloride in MDC (10 mL)

for 20 min. After completion of addition, the reaction

mixture was stirred for 3 h at 20 °C. After completion of

reaction, the reaction mixture was poured into water

(50 mL), extracted with ethyl acetate (2 × 250 mL) and the

combined organic layer was washed with brine solution,

dried over Na₂SO₄and concentrated under vacuum. The

crude residue was puriﬁed by column chromatography on

silica gel (10% ethyl acetate/hexane) to obtain 11-(2-

methoxyphenyl)-1-(2,4,6-trimethoxyphenyl)-undec-2en-1-

A mixture of 9-(2-methoxyphenyl)-nonan-1-al (10a, 1 g,

4.032 mmol), dry THF (20 mL) and ethyl triphenylpho-

sphorane (1.4 g, 4.032 mmol) in a RB ﬂask was reﬂuxed for

3 h. After completion of reaction, the reaction mixture was

concentrated under vacuum. The crude compound was

puriﬁed by column chromatography on silica gel (5% ethyl

acetate/hexane) to obtain 11-(2-methoxyphenyl)-undec-2-

enoic acid ethyl ester (11, 0.318 g, 68%,). ¹H NMR (CDCl₃,

400 MHz): δ 7.04 (1H, dd, J = 3.6, 8.8 Hz, H-6′), 6.88 (1H,

td, J = 17.2, 7.2 Hz, H-4′), 6.85 (1H, td, J = 3.2, 8.4 Hz, H-

3), 6.71 (1H, td, J = 3.6, 8.8 Hz, H-5′), 6.66 (1H, dd, J =

3.2, 8.4 Hz, H-3′), 5.81 (1H, d, J = 17.2 Hz, H-2), 4.21(2H,

m, OCH₂), 3.72 (3H, s, OCH₃), 2.52 (2H, t, J = 6.8 Hz, H-

11), 1.89 (2H, t, J = 6.8 Hz, H-4), 1.66–1.61 (2H, m, H-10),

1.34–1.32 (2H, m, H-5), 1.30 (3H, t, J = 6.8 Hz,

OCH₂CH₃), 1.28–1.21(8H, m, H-6, 7, 8, 9); ¹³C NMR

(CDCl₃, 100 MHz): δ 166.1 (C-1), 162.1 (C-2′), 147.6 (C-

3), 129.8 (C-6′), 127.6 (C-4′), 126.1 (C-1′), 122.6 (C-5′),

119.6 (C-2), 114.8 (C-3′), 59.2 (OCH₂), 56.4 (OCH₃), 32.8

(C-4, 10), 30.5 (C-6, 7), 30.3 (C-8), 30.0 (C-5), 29.8 (C-9),

1

one (13, 580 mg, 65 %). H NMR (CDCl₃, 400 MHz): δ

Med Chem Res

7.15 (1H, td, J = 7.6, 2.4 Hz, H-4′), 7.12 (1H, dd, J = 8.0,

2.4 Hz, H-6′), 6.99 (1H, d, J = 17.2 Hz, H-2), 6.96 (1H, td,

J = 7.6,17.2 Hz, H-3), 6.86 (1H, t, J = 7.6 Hz, H-5′), 6.82

(1H, d, J = 8.0 Hz, H-3′), 6.08 (2H, s, H-3′′, 5′′), 3.85 (9H,

s, OCH₃), 3.73 (3H, s, OCH₃), 2.52 (2H, t, J = 7.6 Hz, H-

11), 1.89 (2H, t, J = 7.6 Hz, H-4), 1.66–1.62 (2H, m, H-10),

1.35–1.33 (2H, m, H-5), 1.29–1.22 (8H, m,H-6, 7, 8, 9);

¹³C NMR (CDCl₃, 100 MHz): δ 188.2 (C-1), 162.8 (C-2′′,

6′′), 161.3 (C-4′′), 156.5 (C-2′), 147.6 (C-3), 129.4 (C-6′),

126.7 (C-4′), 125.3 (C-2), 125.1 (C-1′), 118.7 (C-5′), 113.9

(C-3′), 103.6 (C-1′′), 94.3 (C-3′′, 5′′), 58.4 (OCH₃), 56.1

(OCH₃), 32.8 (C-11), 32.6 (C-4), 30.4 (C-10), 30.3 (C-5),

30.0 (C-9), 29.9 (C-6), 25.8 (C-7, 8); LC-MS: m/z 457.3 (M

+ H)⁺, 479.3 (M + Na)⁺.

washed with brine solution, dried over Na₂SO₄and con-

centrated under vacuum. The residue was puriﬁed by col-

umn chromatography on silica gel (30–40% ethyl acetate/

hexane) to get 11-(2-hydroxyphenyl)-1-(2,4,6-trihydrox-

ylphenyl)-undecan-1-one (15, 268 mg, 35%). mp 58–60 °C;

¹H NMR (d₆-DMSO, 400 MHz): δ 12.21 (2H, s, OH), 10.29

(1H, s, OH), 9.11 (1H, s, OH), 7.01 (1H, d, J = 7.6 Hz, H-

6′), 6.96 (1H, t, J = 7.6 Hz, H-4′), 6.75 (1H, d, J = 7.6 Hz,

H-3′), 6.68 (1H, t, J = 7.6 Hz, H-5′), 5.79 (2H, d, J = 0.8

Hz, H-3′′, 5′′), 2.96 (2H, t, J = 7.2 Hz, H-2), 2.47 (2H, t, J

= 7.2 Hz, H-11), 1.58–1.48 (6H, m, H-3, 4, 10), 1.27 (10H,

m, H-5, 6, 7, 8, 9); ¹³C NMR (d₆-DMSO, 100 MHz): δ

205.2 (C-1), 164.4 (C-4′′), 164.1 (C-2′′, 6′′), 154.9 (C-2′),

129.6 (C-6′), 128.5 (C-4′), 126.4 (C-1′), 118.7 (C-5′), 114.8

(C-3′), 103.8 (C-1′′), 94.9 (C-3′′, 5′′), 43.0 (C-2), 29.5 (C-

10), 29.3 (C-9), 29.0 (C-8), 28.9 (C-4, 5, 6, 7), 24.4 (C-3,

11); LC-MS: m/z 385.2 (M-H)⁻; Q-Tof: m/z 387.2168 (M

+ H)⁺(387.2171 calculated for C₂₃H₃₁O₅).

11-(2-Methoxyphenyl)-1-(2,4,6-trimethoxyphenyl)-undecan-

1-one (14)

A mixture of 11-(2-methoxyphenyl)-1-(2,4,6-trimethox-

yphenyl)-undec-2-en-1-one (13, 400 mg, 0.909 mmol),

ethyl acetate (20 mL) and catalytic amount of 10% palla-

dium on CaCO₃reagent was stirred under H₂atmosphere

for 3 h at rt. After completion of reaction, the reaction

mixture was ﬁltered on celite, washed the celite bed with

ethyl acetate (100 mL) and the ﬁltrate was concentrated

under vacuum. The residue was puriﬁed by column chro-

matography on silica gel (5% ethyl acetate/hexane) to get

11-(2-methoxyphenyl)-1-(2,4,6-trimethoxyphenyl)-unde-

can-1-one (14, 333 mg, 83%). ¹H NMR (CDCl₃, 400 MHz):

δ 7.16 (1H, td, J = 7.6, 2.0 Hz, H-4′), 7.12 (1H, dd, J = 8.0,

2.0 Hz, H-6′), 6.86 (1H, t, J = 7.6 Hz, H-5′), 6.83 (1H, d, J

= 8.0 Hz, H-3′), 6.09 (2H, s, H-3′′, 5′′), 3.81 (6H, s, OCH₃),

3.76 (6H, s, OCH₃), 2.71 (2H, t, J = 7.6 Hz, H-2), 2.59 (2H,

t, J = 8.0 Hz, H-11), 1.65–1.59 (2H, m, H-3), 1.55–1.53

(2H, m, H-10), 1.30 (12H, s, H-4, 5, 6, 7, 8, 9); ¹³C NMR

(CDCl₃, 100 MHz): δ 204.2 (C-1), 162.1 (C-2′′, 6′′), 158.1

(C-4′′), 157.5 (C-2′), 131.5 (C-6′), 129.7 (C-4′), 126.2 (C-

1′), 120.3 (C-5′), 114.2 (C-3′), 110.4 (C-1′′), 90.8 (C-3′′, 5′

′), 55.8 (OCH₃), 55.4 (OCH₃), 55.3 (OCH₃), 45.0 (C-11),

30.1 (C-4), 29.9 (C-10), 29.7 (C-5), 29.6 (C-9), 29.5 (C-6),

23.9 (C-7, 8); LC-MS: m/z 459.3 (M + H)⁺, 481.3 (M +

Na)⁺.

General procedure for 11-(substituted phenyl)-1-

(substituted phenyl)-undec-2-en-1-one (17a–p)

A mixture of suitable 9-(substituted phenyl)-nonan-1-al

(10b–e, 0.0016 mol) and 1-(substituted phenyl)-2-(triphe-

nylphosphonyllidiene)-ethanone (16a–d, 0.0016 mol) and

dry THF (20 mL) was reﬂuxed for 4 h. After completion of

reaction, the reaction mixture was concentrated under

vacuum. The crude residue was puriﬁed by column chro-

matography on silica gel (5% ethyl acetate/hexane) to get

the corresponding 11-(substituted phenyl)-1-(substituted

phenyl)-undec-2en-1-one compound (17a–p) with yields in

the range of 45–53%.

11-(3,4,5-Trimethoxyphenyl)-1-(phenyl)-undec-2-en-1-one

1

(17a) Solid (300 mg, 47%); H NMR (CDCl₃, 400 MHz):

δ 7.85 (2H, d, J = 7.6 Hz, H-2′′, 6′′), 7.52 (1H, t, J = 7.2 Hz,

H-4′′), 7.43 (2H, t, J = 7.6 Hz, H-3′′, 5′′), 6.98 (1H, t, J =

16.4, 7.2 Hz, H-2), 6.97 (1H, d, J = 16.4 Hz, H-3), 6.08

(2H, s, H-2′, 6′), 3.72 (9H, s, OCH₃), 2.55 (2H, t, J = 7.2

Hz, H-11), 1.96 (2H, t, J = 6.8 Hz, H-4), 1.62–1.59, (2H, m,

H-10), 1.35–1.31 (2H, m, H-5), 1.26–1.22 (8H, m, H-6, 7,

8, 9); ¹³C NMR (CDCl₃, 100 MHz): δ 189.8 (C-1), 150.7

(C-3′, 5′), 149.6 (C-3), 137.2 (C-1′′), 136.4 (C-4′′), 134.0

(C-1′), 133.6 (C-4′), 131.9 (C-2′′, 6′′), 129.8 (C-3′′, 5′′),

129.3 (C-2), 105.4 (C-2′, 6′), 58.4 (OCH₃), 58.2 (OCH₃),

36.2 (C-11), 33.6 (C-4), 31.3 (C-10), 29.7 (C-6, 7), 29.6 (C-

8), 29.3 (C-5), 29.1 (C-9); LC-MS: m/z 411.3 (M + H)⁺,

433.4 (M + Na)⁺, 449.2 (M + K)⁺.

11-(2-Hydroxyphenyl)-1-(2,4,6-trihydroxylphenyl)-

undecan-1-one (15)

A mixture of 11-(2-methoxyphenyl)-1-(2,4,6-trimethox-

yphenyl)-undecan-1-one (14, 910 mg, 2.058 mmol), freshly

prepared pyridinium chloride (3 g, 26.08 mmol) was heated

at 170–180 °C for 1 h. After completion of reaction, which

was monitored by TLC (chloroform: acetone [7:3]), the

reaction mixture was poured into water (100 mL), extracted

with ethyl acetate (3 × 300 mL). The organic layer was

11-(3,4-Dimethoxyphenyl)-1-(phenyl)-undec-2-en-1-one

1

(17b) Solid (315 mg, 52%); H NMR (CDCl₃, 400 MHz):

δ 7.85 (2H, d, J = 7.2 Hz, H-2′′, 6′′), 7.51 (1H, t, J = 7.2 Hz,

H-4′′), 7.43 (2H, t, J = 7.6 Hz, H-3′′, 5′′), 6.98 (1H, td, J =

Med Chem Res

6.8, 16.4 Hz, H-3), 6.97 (1H, d, J = 16.8 Hz, H-2), 6.61

(1H, dd, J = 8.0, 3.6 Hz, H-5′), 6.59 (1H, d, J = 3.6 Hz, H-

6′), 6.51 (1H, d, J = 8.4 Hz, H-2′), 3.64 (6H, s, OCH₃), 2.56

(2H, t, J = 7.2 Hz, H-11), 1.96 (2H, t, J = 7.2 Hz, H-4),

1.61–1.59 (2H, m, H-10), 1.35–1.32 (2H, m, H-5),

1.28–1.22 (8H, m, H-6, 7, 8, 9); ¹³C NMR (CDCl₃, 100

MHz): δ 189.8 (C-1), 149.7 (C-3), 149.6 (C-3′), 147.6

(C-4′), 137.6 (C-1′), 134.9 (C-4′′), 132.1 (C-1′), 131.8 (C-2′

′, 6′′), 129.6 (C-3′′, 5′′), 129.3 (C-2), 121.5 (C-6′), 115.2

(C-2′), 113.6 (C-5′), 58.5 (OCH₃), 36.3 (C-11), 33.2 (C-4),

31.3 (C-10), 29.8 (C-6, 7), 29.7 (C-8), 29.6 (C-5), 29.3

(C-9); LC-MS: m/z 381.3 (M + H)⁺, 403.4 (M + Na)⁺.

H-6, 7, 8, 9); ¹³C NMR (CDCl₃, 100 MHz): δ 189.8 (C-1),

167.8 (C-4′′), 162.9 (C-2′′), 150.7 (C-3′, 5′), 149.6 (C-3),

136.0 (C-1′), 133.3 (C-6′′), 132.5 (C-4′), 131.2 (C-2), 115.1

(C-1′′), 107.6 (C-2′, 6′), 106.5 (C-5′′), 103.2 (C-3′′), 36.3

(C-11), 33.2 (C-4), 31.6 (C-10), 29.8 (C-6,7), 29.7 (C-8),

29.4 (C-5), 29.1 (C-9); LC-MS: m/z 457.2 (M + H)⁺, 479.4

(M + Na)⁺.

11-(3,4-Dimethoxyphenyl)-1-(2-hydroxy-4-methoxyphe-

nyl)-undec-2-en-1-one (17f) Solid (300 mg, 45%); ¹H

NMR (CDCl₃, 400 MHz): δ 7.51(1H, d, J = 9.2 Hz, H-6′′),

6.98 (1H, td, J = 7.2, 16.8 Hz, H-3), 6.97 (1H, d, J = 16.8

Hz, H-2), 6.72 (1H, d, J = 8.8 Hz, H-5′), 6.69–6.65 (2H, m,

H-2′, 6′), 6.46–6.41 (2H, m, H-3′′, 5′′), 5.08 (1H, s, OH),

3.71 (3H, s, OCH₃), 2.55 (2H, t, J = 7.6 Hz, H-11), 1.93

(2H, t, J = 7.2 Hz, H-4), 1.69–1.62 (2H, m, H-10),

1.35–1.32 (2H, m, H-5), 1.26–1.21 (8H, m, H-6, 7, 8, 9);

¹³C NMR (CDCl₃, 100 MHz): δ 189.8 (C-1), 167.9 (C-4′′),

162.6 (C-2′′), 150.1 (C-3), 149.7 (C-3′), 147.8 (C-4′), 132.2

(C-1′), 132.1 (C-6′′), 131.8 (C-2), 121.6 (C-6′), 115.3 (C-1′

′), 114.9 (C-2′), 113.2 (C-5′), 108.2 (C-5′′), 103.2 (C-3′′),

36.4 (C-11), 33.3 (C-4), 31.2 (C-10), 30.8 (C-6, 7), 29.8 (C-

8), 29.7 (C-5), 29.3 (C-9); LC-MS: m/z 427.3 (M + H)⁺,

333.4 (M + Na)⁺.

11-(4-Methoxyphenyl)-1-(phenyl)-undec-2-en-1-one

(17c) Solid (280 mg, 50%); ¹H NMR (d₆-DMSO, 400

MHz): δ 7.95 (2H, t, J = 7.6 Hz, H-2′′, 6′′), 7.51 (1H, t, J =

7.6 Hz, H-4′′), 7.45 (2H, t, J = 7.6 Hz, H-3′′, 5′′), 7.08 (2H,

d, J = 8.0 Hz, H-2′, 6′), 6.98 (1H, td, J = 7.6, 16.4 Hz, H-3),

6.97 (1H, d, J = 16.4 Hz, H-2), 6.81 (2H, d, J = 8.0 Hz, H-

3′, 5′), 3.78 (3H, s, OCH₃), 2.53 (2H, t, J = 6.8 Hz, H-11),

1.95 (2H, t, J = 7.2 Hz, H-4), 1.66–1.62 (2H, m, H-10),

1.38–1.34 (2H, m, H-5), 1.29–1.21 (8H, m, H-6, 7, 8, 9);

¹³C NMR (d₆-DMSO, 100 MHz): δ 189.8 (C-1), 157.6 (C-

4′), 149.7 (C-3), 137.8 (C-1′′), 134.6 (C-4′′), 131.2 (C-1′′),

129.8 (C-2′′, 6′′), 129.3 (C-2′), 129.2 (C-2′), 114.2 (C-3′,

5′), 55.9 (OCH₃), 36.0 (C-11), 33.3 (C-4), 31.2 (C-10), 30.6

(C-6, 7), 29.8 (C-8), 29.7 (C-5), 29.3 (C-9); LC-MS: m/z

351.3 (M + H)⁺.

11-(4-Methoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)-

1

undec-2-en-1-one (17g) Solid (310 mg, 49%); H NMR

(CDCl₃, 400 MHz): δ 7.62 (1H, d, J = 9.6 Hz, H-6′′), 7.02

(2H, d, J = 8.4 Hz, H-2′, 6′), 6.98 (1H, td, J = 7.2, 16.8 Hz,

H-3), 6.97 (1H, d, J = 16.8 Hz, H-2), 6.86 (2H, d, J = 8.4

Hz, H-3′, 5′), 6.42–6.39 (2H, m, H-3′′, 5′′), 3.81 (3H, s,

OCH₃), 3.78 (3H, s, OCH₃), 2.55 (2H, t, J = 7.6 Hz, H-11),

1.91 (2H, t, J = 7.6 Hz, H-4), 1.69–1.65 (2H, m, H-10),

1.33–1.30 (2H, m, H-5), 1.27–1.22 (8H, m, H-6, 7, 8, 9);

¹³C NMR (CDCl₃, 100 MHz): δ 189.8 (C-1), 167.8 (C-4′′),

162.8 (C-2′′), 157.9 (C-4′), 149.5 (C-3), 132.0 (C-6′′), 131.3

(C-1′), 129.5 (C-2′, 6′), 126.1 (C-2), 115.2 (C-1′′), 114.8 (C-

3′, 5′), 108.5 (C-5′′), 103.5 (C-3′′), 36.2 (C-11), 33.1 (C-4),

31.2 (C-10), 30.8 (C-6, 7), 29.8 (C-8), 29.7 (C-5), 29.3 (C-

9); LC-MS: m/z 397.3 (M + H)⁺, 419.4 (M + Na)⁺.

11-(phenyl)-1-(phenyl)-undec-2-en-1-one

(17d) Oily

compound, (270 mg, 53%); ¹H NMR (CDCl₃, 400 MHz): δ

7.82 (2H, d, J = 7.2 Hz, H-2′′, 6′′), 7.54 (1H, t, J = 7.6 Hz,

H-4′′), 7.42 (2H, t, J = 7.2 Hz, H-3′′, 5′′), 7.21 (2H, t, J =

8.8 Hz, H-3′, 5′), 7.12 (2H, d, J = 7.6 Hz, H-2′, 6′), 7.10

(1H, t, J = 7.6 Hz, H-4′), 6.98 (1H, td, J = 7.2, 16.8 Hz, H-

3), 6.97 (1H, d, J = 16.8 Hz, H-2), 2.55 (2H, t, J = 6.8 Hz,

H-11), 1.92 (2H, t, J = 7.2 Hz, H-4), 1.66–1.61 (2H, m, H-

10), 1.38–1.33 (2H, m, H-5), 1.29–1.22 (8H, m, H-6, 7, 8,

9); ¹³C NMR (CDCl₃, 100 MHz): δ 189.8 (C-1), 149.8 (C-

3), 138.9 (C-1′), 137.9 (C-1′′), 134.5 (C-4′′), 131.6 (C-2′′, 6′

′), 129.8 (C-3′′, 5′′), 129.2 (C-2′, 6′), 128.6 (C-3′, 5′), 128.2

(C-4′), 126.0 (C-2), 36.2 (C-11), 33.2 (C-4), 31.2 (C-10),

30.6 (C-6, 7), 29.8 (C-8), 29.7 (C-5), 29.3 (C-9); LC-MS:

m/z 321.3 (M + H)⁺, 343.4 (M + Na)⁺.

11-(Phenyl)-1-(2-hydroxy-4-methoxyphenyl)-undec-2-en-

1

1-one (17h) Solid (300 mg, 52%); H NMR (d₆-DMSO,

400 MHz): δ 7.62 (1H, d, J = 9.6 Hz, H-6′′), 7.21 (2H, t, J

= 7.6 Hz, H-3′, 5′), 7.16 (2H, d, J = 7.2 Hz, H-2′, 6′), 7.11

(1H, d, J = 7.2 Hz, H-4′), 6.98 (1H, td, J = 7.2, 16.8 Hz, H-

3), 6.97 (1H, d, J = 16.8 Hz, H-2), 6.41 (1H, dd, J = 7.2,

2.4 Hz, H-5′′), 6.39 (1H, d, J = 2.4 Hz, H-3′′), 5.01 (1H, s,

OH), 3.71 (3H, s, OCH₃), 2.55 (2H, t, J = 7.2 Hz, H-11),

1.92 (2H, t, J = 7.2 Hz, H-4), 1.68–1.62 (2H, m, H-10),

1.39–1.35 (2H, m, H-5), 1.28–1.22 (8H, m, H-6, 7, 8, 9);

¹³C NMR (d₆-DMSO, 100 MHz): δ 189.8 (C-1), 167.9 (C-

4′′), 162.9 (C-2′′), 149.7 (C-3), 138.9 (C-1′), 132.9 (C-6′′),

11-(3,4,5-Trimethoxyphenyl)-1-(2-hydroxy-4-methoxy-

phenyl)-undec-2-en-1-one (17e) Solid (340 mg, 47%); H

1

NMR (CDCl₃, 400 MHz): δ 7.53 (1H, d, J = 8.4 Hz, H-6′′),

6.98 (1H, td, J = 7.2, 16.8 Hz, H-3), 6.97 (1H, d, J = 16.8

Hz, H-2), 6.52–6.47 (2H, m, H-3′′, 5′′), 6.08 (2H, s, H-2′,

6′), 3.86 (3H, s, OCH₃), 3.84 (9H, s OCH₃), 2.55 (2H, t, J

= 6.8 Hz, H-11), 1.94 (2H, t, J = 7.6 Hz, H-4), 1.63–1.60

(2H, m, H-10), 1.33–1.29 (2H, m, H-5), 1.26–1.22 (8H, m,

Med Chem Res

129.8 (C-2′, 3′, 4′, 5′), 129.6 (C-4′), 126.8 (C-2), 116.1 (C-

1′′), 108.4 (C-5′′), 103.5 (C-3′′), 36.2 (C-11), 33.3 (C-4),

31.2 (C-10), 30.8 (C-6, 7), 29.8 (C-8), 29.7 (C-5), 29.3 (C-

9); LC-MS: m/z 365.3 (M−H)⁻.

(C-2′′), 115.8 (C-5′′), 115.1 (C-3′, 5′), 56.4 (OCH₃), 36.2

(C-11), 33.2 (C-4), 31.3 (C-10), 29.8 (C-6, 7), 29.7 (C-8),

29.2 (C-5), 29.3 (C-9); LC-MS: m/z 411.3 (M + H)⁺, 433.4

(M + Na)⁺.

11-(3,4,5-Trimethoxyphenyl)-1-(3,4-dimethoxyphenyl)-

undec-2-en-1-one (17i) Oily compound, (370 mg, 49%);

¹H NMR (CDCl_3,400 MHz): δ 7.68 (1H, dd, J = 1.6,8 Hz,

H-6′′), 7.54 (1H, d, J = 1.6 Hz, H-2′′), 6.98 (1H, td, J = 6.8,

17.2 Hz, H-3), 6.97 (1H, d, J = 17.2 Hz, H-2), 6.88 (1H, d,

J = 8.4 Hz, H-5′′), 6.19 (2H, s, H-2′, 6′), 3.94 (3H, s,

OCH₃), 3.93 (3H, s, OCH₃), 3.84 (3H, s, OCH₃), 3.82

(6H, s, OCH₃), 2.62 (2H, t, J = 7.6 Hz, H-11), 2.11 (2H, t,

J = 8.0 Hz, H-4), 1.69–1.63 (2H, m, H-10), 1.60–1.57 (2H,

m, H-5), 1.33–1.27 (8H, m, H-6, 7, 8, 9); ¹³C NMR (CDCl₃,

100MHz): δ 199.2 (C-1), 156.2 (C-4′′), 152.1 (C-3′, 5′),

149.7 (C-3′′), 147.9 (C-3), 136.7 (C-1′), 136.2 (C-4′),

131.7 (C-1′′), 123.8 (C-2), 122.1 (C-6′′), 111.6 (C-2′′),

110.1 (C-5′′), 103.3 (C-2′, 6′), 56.9 (OCH₃), 56.6 (OCH₃),

56.4 (OCH₃), 56.1 (OCH₃), 38.6 (C-11), 36.3 (C-4), 31.5

(C-10), 29.6 (C-6, 7), 29.4 (C-8), 29.2 (C-5), 29.1 (C-9);

LC-MS: m/z 471.4 (M + H) + , 493.4 (M + Na)⁺, 508.3

(M + k)⁺.

11-(Phenyl)-1-(3,4-dimethoxyphenyl)-undec-2-en-1-one

(17l) White solid (290 mg, 48 %); H NMR (CDCl₃, 400

1

MHz): δ 7.56 (1H, dd, J = 1.6, 8.4 Hz, H-6′′), 7.51 (1H, d,

J = 1.6 Hz, H-2′′), 7.24 (2H, t, J = 8.0 Hz, H-3′, 5′), 7.12

(2H, d, J = 7.2 Hz, H-2′, 6′), 7.06 (1H, t, J = 7.2 Hz, H-4′),

6.98 (1H, td, J = 7.2, 16.8 Hz, H-3), 6.94 (1H, d, J = 16.8

Hz, H-2), 6.81 (1H, d, J = 8.4 Hz, H-5′′), 3.73 (6H, s,

OCH₃), 2.55 (2H, t, J = 7.6 Hz, H-11), 1.93 (2H, t, J = 7.2

Hz, H-4), 1.68–1.62 (2H, m, H-10), 1.36–1.33 (2 H, m, H-

5), 1.29–1.25 (8H, m, H-6, 7, 8, 9); ¹³C NMR (CDCl₃, 100

MHz): δ 189.8 (C-1), 156.8 (C-4′′), 151.3 (C-3′′), 150.7 (C-

3), 138.7 (C-1′), 132.2 (C-1′′), 131.0 (C-2′, 6′), 128.7 (C-3′,

5′), 128.3 (C-4′), 126.2 (C-2), 123.5 (C-6′′), 116.1 (C-2′′),

115.8 (C-5′′), 36.3 (C-11), 33.2 (C-4), 31.3 (C-10), 29.8 (C-

6, 7), 29.7 (C-8), 29.3 (C-5), 29.1 (C-9); LC-MS: m/z 381.3

(M + H)⁺, 403.4 (M + Na)⁺, 419.3 (M + K)⁺.

11-(3,4,5-Trimethoxyphenyl)-1-(2,5-dimethoxyphenyl)-

undec-2-en-1-one (17m) Oily compound, (390 mg, 50%);

¹H NMR (CDCl₃, 400 MHz): δ 7.21 (1H, d, J = 3.2 Hz, H-

6′′), 7.02 (1H, dd, J = 3.2, 8.8 Hz, H-4′′), 6.98 (1H, td, J =

7.2, 16.8 Hz, H-3), 6.97 (1H, d, J = 16.8 Hz, H-2), 6.88

(1H, d, J = 8.4 Hz, H-3′′), 6.12 (2H, s, H-2′, 6′), 3.86 (9H, s,

OCH₃), 3.83 (3H, s, OCH₃), 3.78 (3H, s, OCH₃), 2.55 (2H,

t, J = 7.2 Hz, H-11), 1.94 (2H, t, J = 7.2 Hz, H-4),

1.66–1.62 (2H, m, H-10), 1.39–1.36 (2H, m, H-5),

1.29–1.22 (8H, m, H-6, 7, 8, 9); ¹³C NMR (CDCl₃, 100

MHz): δ 189.8 (C-1), 153.6 (C-2′′), 150.6 (C-5′′), 149.8 (C-

3′, 5′), 146.1 (C-3), 137.2 (C-1′), 134.2 (C-4′), 133.0 (C-2),

122.2 (C-1′′), 121.9 (C-4′′), 116.8 (C-6′′), 115.8 (C-3′′),

106.5 (C-2′, 6′), 36.4 (C-11), 33.3 (C-4), 31.2 (C-10), 30.4

(C-6, 7), 29.8 (C-8), 29.7 (C-5), 29.3 (C-9); LC-MS: m/z

471.3 (M + H)⁺, 493.4 (M + Na)⁺.

11-(3,

4-Dimethoxyphenyl)-1-(3,4-dimethoxyphenyl)-

1

undec-2-en-1-one (17j) White solid (370 mg 52 %); H

NMR (CDCl₃, 400 MHz): δ 7.24 (1H, d, J = 3.2 Hz, H-6′′),

6.98 (1H, td, J = 7.2, 16.8 Hz, H-3), 6.97 (1H, d, J = 16.8

Hz, H-2), 6.96 (1H, dd, J = 3.3, 8.4 Hz, H-5′′), 6.82 (1H, d,

J = 8.8 Hz, H-5′′), 6.76 (1H, d, J = 8.4 Hz, H-5′), 6.71–6.68

(2H, m, H-2′, 6′), 3.72 (6H, s, OCH₃), 3.69 (6H, s, OCH₃),

2.55 (2H, t, J = 7.6 Hz, H-11), 1.92 (2H, t, J = 7.2 Hz, H-

4), 1.69–1.63 (2H, m, H-10), 1.36–1.34 (2H, m, H-5),

1.28–1.23 (8H, m, H-6, 7, 8, 9); ¹³C NMR (CDCl₃, 100

MHz): δ 189.8 (C-1), 155.2 (C-4′′), 151.9 (C-3′′), 149.6 (C-

3), 149.3 (C-3′), 147.9 (C-4′), 132.3 (C-1′), 132.0 (C-1′′),

131.8 (C-2), 123.4 (C-6′′), 121.8 (C-6′), 116.8 (C-2′′), 115.6

(C-5′′), 114.2 (C-2′, 5′), 58.2 (OCH₃), 36.3 (C-11), 33.2 (C-

4), 31.3 (C-10), 29.8 (C-6, 7), 29.7 (C-8), 29.3 (C-5), 29.1

(C-9); LC-MS: m/z 341.3 (M + H)⁺, 363.4 (M + Na)⁺.

11-(3,4-Dimethoxyphenyl)-1-(2,5-dimethoxyphenyl)-

undec-2-en-1-one (17n) White solid (350 mg, 50%); H

1

11-(4-Methoxyphenyl)-1-(3,4-dimethoxyphenyl)-undec-2-

en-1-one (17k) Solid (300 mg, 46%); H NMR (CDCl₃,

NMR (CDCl₃, 400 MHz): δ 7.52 (1H, dd, J = 1.6, 8.4 Hz,

H-6′′), 7.51 (1H, d, J = 1.6 Hz, H-4′′), 6.98 (1H, td, J = 7.2,

16.8 Hz, H-3), 6.97 (1H, d, J = 16.8 Hz, H-2), 6.89 (1H, d,

J = 8.4 Hz, H-3′′), 6.68 (1H, d, J = 7.6 Hz, H-5′), 6.64 (2H,

m, H-2′, 6′), 3.74 (6H, s, OCH₃), 3.69 (6H, s, OCH₃), 2.55

(2H, t, J = 7.3 Hz, H-11), 1.92 (2H, t, J = 7.2 Hz, H-4),

1.66–1.64 (2H, m, H-10), 1.32–1.30 (2H, m, H-5),

1.28–1.22 (8H, m, H-6, 7, 8, 9); ¹³C NMR (CDCl₃, 100

MHz): δ 189.8 (C-1), 155.8 (C-5′′), 153.5 (C-2′′), 149.6 (C-

3), 149.4 (C-3′), 147.0 (C-4′), 132.2 (C-1′), 131.9 (C-2),

122.2 (C-1′′), 121.8 (C-6′), 121.6 (C-4′′), 116.8 (C-6′′),

115.8 (C-3′′), 114.2 (C-2′, 5′), 36.3 (C-11), 33.2 (C-4), 31.3

1

400 MHz): δ 7.68 (1H, dd, J = 1.6, 8.4 Hz, H-6′′), 7.55 (1H,

d, J = 1.6 Hz, H-2′′), 7.09 (2H, d, J = 8.4 Hz, H-2′, 6′), 6.98

(1H, td, J = 7.2, 16.8 Hz, H-3), 6.92 (1H, d, J = 16.8 Hz, H-

2), 6.86 (1H, d, J = 8.4 Hz, H-5′′), 6.83 (2H, d, J = 8.8 Hz,

H-3′, 5′), 3.72 (9H, s, OCH₃), 2.55 (2H, t, J = 7.2 Hz, H-

11), 1.93 (2H, t, J = 7.2 Hz, H-4), 1.69–1.63 (2H, m, H-10),

1.36–1.31 (2H, m, H-5), 1.28–1.22 (8H, m, H-6, 7, 8, 9);

¹³C NMR (CDCl₃, 100 MHz): δ 189.8 (C-1), 157.6 (C-4′),

156.5 (C-4′′), 151.3 (C-3′′), 149.7 (C-3), 132.8 (C-1′), 131.2

(C-1′′), 129.6 (C-2′, 6′), 125.7 (C-2), 122.9 (C-6′′), 116.1

Med Chem Res

(C-10), 30.6 (C-6, 7), 29.8 (C-8), 29.6 (C-5), 29.3 (C-9);

LC-MS: m/z 441.3 (M + H)⁺, 463.4 (M + Na)⁺, 479.2 (M

+ K)⁺.

11-(3,4,5-Trimethoxyphenyl)-1-(phenyl)-undecan-1-one

(18a) White waxy compound, (370 mg, 82%); H NMR

1

(CDCl_3,400 MHz): δ 7.95 (2H, d, J = 8 Hz, H-2′′, 6′′), 7.54

(1H, t, J = 6.8 Hz, H-4′′), 7.44 (2H, t, J = 8.0, H-3′′, 5′′),

6.39 (2H, s, H-2′, 6′), 3.84 (6H, s, OCH₃), 3.82 (3H, s,

OCH₃), 2.95 (2H, t, J = 7.2 Hz, H-2), 2.54 (2H, t, J = 8.0

Hz, H-11), 1.77–1.69 (2H, m, H-3), 1.63–1.56 (2H, m, H-

10), 1.34–1.25 (12H, m, H- 4, 5, 6, 7, 8, 9); ¹³C NMR

(CDCl₃, 100 MHz): δ 200.5 (C-1), 153.1 (C-3′, 5′), 138.7

(C-1′′), 137.2 (C-1′), 136.2 (C-4′′), 132.8 (C-4′), 128.6 (C-2′

′, 6′′), 128.1 (C-3′′, 5′′), 105.5 (C-2′, 6′), 60.8 (OCH₃), 56.1

(OCH₃), 38.6 (C-2), 36.4 (C-11), 31.6 (C-10), 29.6 (C-6, 7,

8), 29.5 (C-5), 29.4 (C-4, 9), 24.4 (C-3); LC-MS: m/z 413.4

(M + H)⁺, 435.4 (M + Na)⁺, 451.3 (M + K)⁺; Q-Tof: m/z

413.2697 (M + H)⁺(413.2692 calculated for C₂₆H₃₇O₄).

11-(4-Methoxyphenyl)-1-(2,5-dimethoxyphenyl)-undec-2-

en-1-one (17o) White solid (330 mg, 51%); ¹H NMR

(CDCl₃, 400 MHz): δ 7.22 (1H, d, J = 3.2 Hz, H-6′′), 7.06

(2H, d, J = 8.8 Hz, H-2′, 6′), 6.98 (1H, td, J = 7.2, 16.8 Hz,

H-3), 6.97 (1H, d, J = 16.8 Hz, H-2), 6.92 (1H, dd, J = 3.2,

8.8 Hz, H-4′′), 6.86 (1H, d, J = 8.8 Hz, H-3′′), 6.81 (2H, d,

J = 8.8 Hz, H-3′, 5′), 3.82 (2H, s, OCH₃), 3.81 (3H, s,

OCH₃), 3.78 (3H, s, OCH₃), 2.55 (2H, t, J = 7.2 Hz, H-11),

1.94 (2H, t, J = 7.2 Hz, H-4), 1.62–159 (2H, m, H-10),

1.37–1.34 (2H, m, H-5), 1.28–1.22 (8H, m, H-6, 7, 8, 9);

¹³C NMR (CDCl₃, 100 MHz): δ 189.8 (C-1), 158.8 (C-4′),

153.6 (C-2′′), 152.9 (C-5′′), 149.8 (C-3), 132.8 (C-1′), 131.2

(C-2′, 6′), 130.1 (C-2), 129.2 (C-1′′), 124.2 (C-4′′), 116.8

(C-6′′), 116.2 (C-3′′), 115.2 (C-3′, 5′), 36.3 (C-11), 33.3 (C-

4), 31.4 (C-10), 29.8 (C-6, 7), 29.7 (C-8), 29.5 (C-5), 29.3

(C-9); LC-MS: m/z 411.3 (M + H)⁺, 433.4 (M + Na)⁺.

11-(3,4-Dimethoxyphenyl)-1-(phenyl)-undecan-1-one

(18b) White solid (365 mg, 87%); mp 44–46 °C; ¹H NMR

(CDCl₃, 400 MHz): δ 7.95 (2H, d, J = 7.2 Hz, H-2′′, 6′′),

7.55 (1H, t, J = 7.2 Hz, H-4′′), 7.45 (2H, t, J = 7.2 Hz, H-3′′,

5′′), 6.78 (1H, d, J = 8.8 Hz, H-5′), 6.72–6.70 (2H, m, H-2′,

6′), 3.87 (3H, s, OCH₃), 3.85 (3H, s, OCH₃), 2.96 (2H, t, J

= 7.6 Hz, H-2), 2.54 (2H, t, J = 7.6 Hz, H-11), 1.76–1.69

(2H, m, H-10), 1.59–1.54 (2H, m, H-3), 1.29 (12H, brs, H-

4, 5, 6, 7, 8, 9); ¹³C NMR (CDCl₃, 100 MHz): δ 200.5 (C-

1), 148.8 (C-3′), 147.1 (C-4′), 137.2 (C-1′′), 135.7 (C-4′′),

132.8 (C-1′), 128.5 (C-2′′, 6′′), 128.0 (C-3′′, 5′′), 120.2 (C-

6′), 111.9 (C-2′), 111.5 (C-5′), 55.9 (OCH₃), 55.8 (OCH₃),

38.6 (C-2), 35.6 (C-11), 31.6 (C-10), 29.5 (C-6, 7, 8), 29.4

(C-5), 29.3 (C-9), 29.2 (C-4), 24.4 (C-3); LC-MS: m/z 383.4

(M + H)⁺, 405.4 (M + Na)⁺, 421.3 (M + K)⁺; Q-Tof: m/z

383.2593 (M + H)⁺(383.2586 calculated for C₂₅H₃₅O₃).

11-(Phenyl)-1-(2,5-dimethoxyphenyl)-undec-2-en-1-one

1

(17p) Oily substance, (285 mg, 47%) H NMR (CDCl₃,

400 MHz): δ 7.24 (2H, t, J = 8.0 Hz, H-3′, 5′), 7.20 (1H, d,

J = 3.2 Hz, H-6′′), 7.12 (2H, d, J = 7.2 Hz, H-2′, 6′), 7.08

(1H, t, J = 7.2 Hz, H-4′), 6.98 (1H, td, J = 7.2, 16.8 Hz, H-

2), 6.97 (1H, d, J = 16.8 Hz, H-3), 6.81 (1H, dd, J = 2.8,

8.8 Hz, H-4′′), 6.76 (1H, d, J = 9.2 Hz, H-3′′), 3.73 (6H, s,

OCH₃), 2.55 (2H, t, J = 7.6 Hz, H-11), 1.94 (2H, t, J = 7.2

Hz, H-4), 1.66–1.62 (2H, m, H-10), 1.35–1.32 (2H, m, H-

5), 1.28–1.22 (8H, m, H-6, 7, 8, 9); ¹³C NMR (CDCl₃, 100

MHz): δ 189.8 (C-1), 154.5 (C-2′′), 150.7 (C-5′′), 147.9 (C-

3), 139.7 (C-1′), 132.2 (C-2′, 3′, 5′, 6′), 129.6 (C-2), 127.0

(C-4′), 126.1 (C-1′′), 121.2 (C-4′′), 116.8 (C-6′′), 116.1 (C-

3′′), 36.0(C-11), 33.3 (C-4), 31.3 (C-10), 29.8 (C-6, 7), 29.7

(C-8), 29.3 (C-5), 29.2 (C-9); LC-MS: m/z 381.3 (M + H)⁺,

403.4 (M + Na)⁺, 419.2 (M + K)⁺.

11-(4-Methoxyphenyl)-1-(phenyl)-undecan-1-one (18c)

white solid (300 mg, 78%); mp 50–52 °C; ¹H NMR

(CDCl₃, 400 MHz): δ 7.96 (2H, d, J = 7.6 Hz, H-2′′, 6′′),

7.55 (1H, t, J = 7.6 Hz, H-4′′), 7.45 (2H, t, J = 7.6 Hz,

H-3′′, 5′′), 7.08 (2H, d, J = 8.0 Hz, H-2′, 6′), 6.81 (2H, d, J

= 8.4 Hz, H-3′, 5′), 3.78 (3H, s, OCH₃), 2.95 (2H, t, J = 7.6

Hz, H-2), 2.53 (2H, t, J = 8.0 Hz, H-11), 1.76–1.69 (2H, m,

H-10),1.55 (2H, brs, H-3), 1.29 (12H, brs, H-4, 5, 6, 7, 8,

9); ¹³C NMR (CDCl₃, 100 MHz): δ 200.6 (C-1), 157.7 (C-

4′), 137.3 (C-1′′), 135.1 (C-4′′), 132.8 (C-1′), 129.3 (C-2′,

6′), 128.6 (C-2′′, 6′′), 128.1 (C-3′′, 5′′), 113.7 (C-3′, 5′), 55.3

(OCH₃), 38.7 (C-2), 35.1 (C-11), 31.7 (C-10), 29.5 (C-6, 7,

8), 29.49 (C-5), 29.4 (C-9), 29.2 (C-4), 24.4 (C-3); LC-MS:

m/z 353.3 (M + H)⁺, 375.3 (M + Na)⁺, 391.2 (M + K)⁺;

Q-Tof: m/z 353.2489 (M + H)⁺(353.2481 calculated for

C₂₄H₃₃O₂).

General procedure for 11-(substituted phenyl)-1-

(substituted phenyl)-undecan-1-one (18a–p)

A mixture of 11-(substituted phenyl)-1-(substituted phenyl)-

undec-2-en-1-one (17a–p, 1.1 mmol), ethyl acetate (20 mL),

catalytic amount of 5 % palladium on CaCO₃was stirred

under hydrogen atmosphere for 2 h at room temperature.

After completion of reaction, the reaction mixture was ﬁl-

tered on super cell and washed with ethyl acetate. The

combined ﬁltrate was concentrated under vacuum and the

residue was puriﬁed by column chromatography on silica

gel (5% ethyl acetate/hexane) to obtain the corresponding

11-(substituted phenyl)-1-(substituted phenyl)-l-undecan-1-

one (18a–p) with yields in the range of 75–87%.

11-(Phenyl)-1-(phenyl)-undecan-1-one (18d) Oily com-

pound, (270 mg, 76%); ¹H NMR (CDCl₃, 400 MHz): δ 7.95

(2H, d, J = 7.2 Hz, H-2′′, 6′′), 7.54 (1H, t, J = 7.2 Hz, H-4′′),

Med Chem Res

7.44 (2H, t, J = 7.6 Hz, H-3′′, 5′′), 7.26 (2H, t, J = 8.8 Hz,

H-3′, 5′), 7.17 (2H, d, J = 7.6 Hz, H-2′, 6′), 7.15 (1H, t, J =

7.6 Hz, H-4′), 2.95 (2H, t, J = 7.6 Hz, H-2), 2.59 (2H, t, J =

8.0 Hz, H-11), 1.76–1.69 (2H, m, H-10), 1.64–1.56 (2H, m,

H-3), 1.38–1.28 (12H, m, H-4, 5, 6, 7, 8, 9); ¹³C NMR

(CDCl₃, 100 MHz): δ 200.5 (C-1), 142.9 (C-1′), 137.2

(C-1′′), 132.8 (C-4′′), 128.5 (C-2′′, 6′′), 128.4 (C-3′′, 5′′),

128.2 (C-2′, 6′), 128.0 (C-3′, 5′), 125.5 (C-4′), 38.6 (C-2),

35.9 (C-11), 31.9 (C-10), 31.4 (C-6, 7), 29.5 (C-8), 29.4 (C-

5), 29.3 (C-9), 29.2 (C-4), 24.4 (C-3); LC-MS: m/z 323.3

(M + H) + , 345.3 (M + Na)+; Q-Tof: m/z 323.2373 (M +

H)⁺(323.2375 calculated for C₂₃H₃₁O).

1.73–1.67 (2H, m, H-10), 1.63–1.55 (2H, m, H-3), 1.30

(12H, brs, H-4, 5, 6, 7, 8, 9); ¹³C NMR (CDCl₃, 100 MHz):

δ 202.8 (C-1), 165.9 (C-4′′), 165.5 (C-2′′), 157.7 (C-4′),

134.9 (C-6′′), 131.6 (C-1′), 129.2 (C-2′, 6′), 113.7 (C-3′, 5′),

107.5 (C-5′′), 101.0 (C-3′′), 55.5 (OCH₃), 55.3 (OCH₃),

43.9 (C-2), 38.0 (C-11), 35.0 (C-10), 31.7 (C-6, 7), 29.5 (C-

8), 29.4 (C-5), 29.3 (C-9), 29.2 (C-4), 24.9 (C-3); LC-MS:

m/z 397 (M-H)⁻; Q-Tof: m/z 399.2523 (M + H)⁺

(399.2535 calculated for C₂₅H₃₅O₄).

11-(Phenyl)-1-(2-hydroxy-4-methoxyphenyl)-undecan-1-

one (18h) White waxy compound (335 mg, 83%); ¹H

NMR (CDCl₃, 400 MHz): δ 12.91 (1H, s, OH), 7.64 (1H, d,

J = 9.6 Hz, H-6′′), 7.26 (2H, t, J = 7.2 Hz, H-3′, 5′), 7.17

(2H, d, J = 7.2 Hz, H-2′, 6′), 7.15 (1H, t, J = 7.2 Hz, H-4′),

6.42 (1H, dd, J = 7.2, 2.4 Hz, H-5′′), 6.41 (1H, d, J = 2.4

Hz, H-3′′), 3.81 (3H, s, OCH₃), 2.87 (2H, t, J = 7.6 Hz, H-

2), 2.59 (2H, t, J = 7.6 Hz, H-11), 1.74–1.67 (2H, m, H-10),

1.62–1.58 (2H, m, H-3), 1.30 (12H, s, H-4, 5, 6, 7, 8, 9);

¹³C NMR (CDCl₃, 100 MHz): δ 202.7 (C-1), 165.9 (C-4′′),

165.9 (C-2′′), 142.9 (C-1′), 142.8 (C-6′′), 131.6 (C-2′, 6′),

128.4 (C-3′, 5′), 125.6 (C-5′), 113.6 (C-1′′), 107.5 (C-5′′),

101.0 (C-3′′), 55.5 (OCH₃), 43.9 (C-2), 38.0 (C-11), 35.9

(C-10), 31.4 (C-6), 29.5 (C-7), 29.4 (C-8), 29.3 (C-5), 29.2

(C-9), 29.1 (C-4), 24.9 (C-3); LC-MS: m/z 367.3 (M-H)⁻;

Q-Tof: m/z 369.2421 (M + H)⁺(369.2430 calculated for

C₂₄H₃₃O₃).

11-(3,4,5-Trimethoxyphenyl)-1-(2-hydroxy-4-methoxyphe-

nyl)-undecan-1-one (18e) White waxy compound (410

1

mg, 81%); H NMR (CDCl_3,400 MHz): δ 12.89 (1H,s,

OH), 7.65 (1H, d, J = 8.8 Hz, H-6′′), 6.44–6.42 (2H, m, H-

3′′, 5′′), 6.39 (2H, s, H-2′, 6′), 3.84 (6H, s, OCH₃), 3.82 (6H,

s, OCH₃), 2.88 (2H, t, J = 7.6 Hz, H-2), 2.54 (2H, t, J = 8.0

Hz, H-11), 1.76–1.68 (4H, m, H-3, 10), 1.32 (12H, m, H-4,

5, 6, 7, 8, 9); ¹³C NMR (CDCl₃, 100 MHz): δ 205.1 (C-1),

165.9 (C-4′′), 165.4 (C-2′′), 153.0 (C-3′, 5′), 138.6 (C-1′),

138.5 (C-6′′), 136.1 (C-4′), 113.5 (C-1′′), 107.4 (C-2′, 6′),

105.4 (C-5′′), 100.9 (C-3′′), 60.7 (OCH₃), 56.0 (OCH₃),

55.4 (OCH₃), 43.8 (C-2), 36.3 (C-11), 31.5 (C-10), 29.5 (C-

6, 7, 8), 29.4 (C-5), 29.3 (C-9), 29.2 (C-4), 24.8 (C-3); LC-

MS: m/z 457.4 (M−H)⁻.

11-(3,4-Dimethoxyphenyl)-1-(2-hydroxy-4-methoxyphe-

nyl)-undecan-1-one (18f) waxy solid (350 mg, 75%); H

11-(3,4,5-Trimethoxyphenyl)-1-(3,4-dimethoxyphenyl)-

undecan-1-one (18i) Oily compound (450 mg, 86%); H

1

NMR (CDCl₃, 400 MHz): δ 12.89 (1H, s, OH), 7.65 (1H, d,

J = 9.6 Hz, H-6′′), 6.78 (1H, d, J = 8.8 Hz, H-5′), 6.71–6.70

(2H, m, H-2′, 6′), 6.44–6.42 (2H, m, H-3′′, 5′′), 3.87 (3H, s,

OCH₃), 3.85 (3H, s, OCH₃), 3.83 (3H, s, OCH₃), 2.88 (2H,

t, J = 7.2 Hz, H-2), 2.54 (2H, t, J = 7.6 Hz, H-11),

1.76–1.68 (2H, m, H-10), 1.64–1.55 (2H, m, H-3),

1.35–1.26 (12H, m, H-4, 5, 6, 7, 8, 9); ¹³C NMR (CDCl₃,

100 MHz): δ 202.7 (C-1), 165.9 (C-4′′), 148.8 (C-2′′), 147.1

(C-3′), 135.6 (C-4′), 131.5 (C-1′), 120.2 (C-6′′), 113.5

(C-6′), 111.9 (C-1′′), 111.4 (C-2′, 5′), 107.5 (C-5′′), 101.0

(C-3′′), 55.9 (OCH₃), 55.8 (OCH₃), 55.5 (OCH₃), 43.8

(C-2), 37.9 (C-11), 35.5 (C-10), 31.6 (C-6, 7), 29.5 (C-8),

29.4 (C-5), 29.3 (C-9), 29.2 (C-4), 24.9 (C-3); LC-MS: m/z

429.4 (M + H)⁺, 451.4 (M + Na)⁺; Q-Tof: m/z 429.2703

(M + H)⁺(429.2700 calculated for C₂₆H₃₇O₅).

NMR (CDCl_3,400 MHz): δ 7.58 (1H, dd, J = 1.6,8.0 Hz,

H-6′′), 7.53 (1H, d, J = 1.6 Hz, H-2′′), 6.85 (1H, d, J = 8.4,

H-5′′), 6.39 (2H, s, H-2′, 6′), 3.94 (3H, s, OCH₃), 3.93 (3H,

s, OCH₃), 3.84 (3H, s, OCH₃), 3.82 (3H, s, OCH₃), 2.91

(2H, t, J = 7.6 Hz, H-2), 2.54 (2H, t, J = 8.0 Hz, H-11),

1.76–1.69 (2H, m, H-10), 1.60–1.56 (2H, m, H-3),

1.34–1.25 (12H, m, H-4, 5, 6, 7, 8, 9); ¹³C NMR (CDCl₃,

100 MHz): δ 199.2 (C-1), 153.2 (C-4′′), 153.1 (C-3′, 5′),

149.1 (C-3′′), 138.7 (C-1′), 136.2 (C-1′′), 130.5 (C-4′),

122.6 (C-6′′), 110.4 (C-2′′), 110.1 (C-5′′), 105.5 (C-2′, 6′),

60.8 (OCH₃), 56.1 (OCH₃), 56.0 (OCH₃), 55.9 (OCH₃),

38.1 (C-2), 36.4 (C-11), 31.5 (C-10), 29.5 (C-6, 7, 8), 29.4

(C-5), 29.3 (C-9), 29.2 (C-4), 24.7 (C-3); LC-MS: m/z 473.4

(M + H)+, 495.4 (M + Na)⁺, 511.3 (M + k)⁺; Q-Tof: m/z

473.2908 (M + H)⁺(473.2903 calculated for C₂₈H₄₁O₆).

11-(4-Methoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)-

undecan-1-one (18g) White solid (370 mg, 85%); mp

48–50 °C; ¹H NMR (CDCl₃, 400 MHz): δ 12.9 (1H, s, OH),

7.65 (1H, d, J = 9.2 Hz, H-6′′), 7.08 (2H, d, J = 8.4 Hz, H-

2′, 6′), 6.81 (2H, d, J = 8.4 Hz, H-3′, 5′), 6.44–6.42 (2H, m,

H-3′′, 5′′), 3.83 (3H, s, OCH₃), 3.78 (3H, s, OCH₃), 2.88

(2H, t, J = 7.6 Hz, H-2), 2.53 (2H, t, J = 7.6 Hz, H-11),

11-(3,4-Dimethoxyphenyl)-1-(3,4-dimethoxyphenyl)-unde-

can-1-one (18j) White solid (410 mg, 84 %); mp 74–76 °C;

¹H NMR (CDCl₃, 400 MHz): δ 7.20 (1H, d, J = 3.2 Hz,

H-6′′), 6.99 (1H, dd, J = 3.2, 8.8 Hz, H-2′′), 6.89 (1H, d, J =

8.8 Hz, H-5′′), 6.78 (1H, d, J = 8.4 Hz, H-5′), 6.72–6.70

(2H, m, H-2′, 6′), 3.87 (3H, s, OCH₃), 3.85 (3H, s, OCH₃),

3.84 (3H, s, OCH₃), 3.78 (3H, s, OCH₃), 2.95 (2H,

Med Chem Res

t, J = 7.6 Hz, H-2), 2.54 (2H, t, J = 7.6 Hz, H-11),

1.69–1.62 (2H, m, H-10), 1.59–1.52 (2H, m, H-3),

1.30–1.25 (12H, m, H-4, 5, 6, 7, 8, 9); ¹³C NMR (CDCl₃,

100 MHz): δ 202.8 (C-1), 153.6 (C-4′′), 152.8 (C-3′′), 148.8

(C-3′), 147.1 (C-4′), 135.7 (C-1′), 129.2 (C-1′′), 120.2

(C-6′′), 119.4 (C-6′), 113.2 (C-2′′), 111.9 (C-5′′), 111.4

(C-2′, 5′), 56.1 (OCH₃), 55.9 (OCH₃), 55.84 (OCH₃), 55.8

(OCH₃), 43.7 (C-2), 35.6 (C-11), 31.6 (C-10), 29.5 (C-6, 7,

8), 29.4 (C-5), 29.3 (C-9), 29.2 (C-4), 24.4 (C-3); LC-MS:

m/z 443.4 (M + H)⁺, 465.3 (M + Na)⁺, 481.3 (M + K)⁺;

Q-Tof: m/z 443.2805 (M + H)⁺(443.2797 calculated for

C₂₇H₃₉O₅).

Hz, H-3′′), 6.39 (2H, s, H-2′, 6′), 3.86 (9H, s, OCH₃), 3.82

(3H, s, OCH₃), 3.78 (3H, s, OCH₃), 2.95 (2H, t, J = 7.2 Hz,

H-2), 2.54 (2H, t, J = 8.0 Hz, H-11), 1.66–1.60 (6H, m, H-

3, 4, 10), 1.31–1.29 (10H, m, H-5, 6, 7, 8, 9); ¹³C NMR

(CDCl₃, 100 MHz): δ 202.8 (C-1), 153.6 (C-2′′), 153.1

(C-5′′), 152.8 (C-3′, 5′), 138.7 (C-1′), 136.2 (C-4′), 129.2

(C-1′′), 119.4 (C-4′′), 114.1 (C-6′′), 113.2 (C-3′′), 105.5

(C-2′, 6′), 60.6 (OCH₃), 56.1 (OCH₃), 55.8 (OCH₃), 43.7

(C-2), 36.4 (C-11), 31.5 (C-10), 29.5 (C-6, 7, 8), 29.4 (C-5),

29.3 (C-9), 29.2 (C-4), 24.4 (C-3); LC-MS: m/z 473.4 (M +

H)+, 495.4 (M + Na)⁺; Q-Tof: m/z 473.2917 (M + H)⁺

(473.2903 calculated for C₂₈H₄₁O₆).

11-(4-Methoxyphenyl)-1-(3,4-dimethoxyphenyl)-undecan-

1-one (18k) Oily compound (360 mg, 80%); ¹H NMR

(CDCl₃, 400 MHz): δ 7.58 (1H, dd, J = 1.6, 8.4 Hz, H-6′′),

7.53 (1H, d, J = 1.6 Hz, H-2′′), 7.08 (2H, d, J = 8.4 Hz, H-

2′, 6′), 6.87 (1H, d, J = 8.4 Hz, H-5′′), 6.81 (2H, d, J = 8.8

Hz, H-3′, 5′), 3.94 (3H, s, OCH₃), 3.93 (3H, s, OCH₃), 3.78

(3H, s, OCH₃), 2.91 (2H, t, J = 7.2 Hz, H-2), 2.53 (2H, t, J

= 7.6 Hz, H-11), 1.74–1.68 (2H, m, H-10), 1.58–1.55 (2H,

m, H-3), 1.38–1.28 (12H, m, H-4, 5, 6, 7, 8, 9); ¹³C NMR

(CDCl₃, 100 MHz): δ 199.2 (C-1), 157.7 (C-4′), 153.2 (C-4′′),

149.1 (C-3′′), 135.1 (C-1′), 130.5 (C-1′′), 129.2 (C-2′, 6′),

122.7 (C-6′′), 113.7 (C-2′′), 110.4 (C-5′′), 110.1 (C-3′, 5′),

56.1 (OCH₃), 56.0 (OCH₃), 55.3 (OCH₃), 38.2 (C-2), 35.1

(C-11), 31.7 (C-10), 29.6 (C-6, 7, 8), 29.5 (C-5), 29.4 (C-9),

29.3 (C-4), 24.8 (C-3); LC-MS: m/z 413.3 (M + H)⁺, 435.2

(M + Na)⁺, 451.2 (M + K)⁺; Q-Tof: m/z 413.2704 (M +

H)⁺(413.2692 calculated for C₂₆H₃₇O₄).

11-(3,4-Dimethoxyphenyl)-1-(2,5-dimethoxyphenyl)-unde-

can-1-one (18n) Waxy compound (405 mg, 83%); ¹H

NMR (CDCl₃, 400 MHz): δ 7.58 (1H, dd, J = 1.6, 8.4 Hz,

H-6′′), 7.53 (1H, d, J = 1.6 Hz, H-4′′), 6.88 (1H, d, J = 8.4

Hz, H-3′′), 6.78 (1H, d, J = 7.6 Hz, H-5′), 6.71–6.70 (2H,

m, H-2′, 6′), 3.94 (3H, s, OCH₃), 3.93 (3H, s, OCH₃), 3.87

(3H, s, OCH₃), 3.85 (3H, s, OCH₃), 2.91 (2H, t, J = 7.6 Hz,

H-2), 2.54 (2H, t, J = 7.6 Hz, H-11), 1.75–1.68 (2H, m, H-

10), 1.59–1.54 (2H, m, H-3), 1.299 (12H, brs, H-4, 5, 6, 7,

8, 9); ¹³C NMR (CDCl₃, 100 MHz): δ 199.2 (C-1), 153.2

(C-2′′), 149.1 (C-5′′), 148.8 (C-3′), 147.1 (C-4′), 135.7 (C-

1′), 130.5 (C-1′′), 122.6 (C-6′), 120.2 (C-4′′), 111.9 (C-6′′),

111.4 (C-3′′), 110.4 (C-2′), 110.1 (C-6′), 56.0 (OCH₃), 55.9

(OCH₃), 55.8 (OCH₃), 38.1 (C-2), 35.6 (C-11), 29.5 (C-10),

29.4 (C-5, 6, 7, 8), 29.3 (C-9), 29.2 (C-4), 24.8 (C-3); LC-

MS: m/z 443.4 (M + H)⁺, 465.4 (M + Na)⁺; Q-Tof: m/z

443.2792 (M + H)⁺(443.2797 calculated for C₂₇H₃₉O₅).

11-(Phenyl)-1-(3,4-dimethoxyphenyl)-undecan-1-one

11-(4-Methoxyphenyl)-1-(2,5-dimethoxyphenyl)-undecan-

1-one (18o) White solid (390 mg, 86%); mp 78–82 °C; ¹H

NMR (CDCl₃, 400 MHz): δ 7.21 (1H, d, J = 3.2 Hz, H-6′′),

7.08 (2H, d, J = 8.8 Hz, H-2′, 6′), 6.99 (1H, dd, J = 3.2, 8.8

Hz, H-4′′), 6.88 (1H, d, J = 8.8 Hz, H-3′′), 6.81 (2H, d, J =

8.8 Hz, H-3′, 5′), 3.84 (3H, s, OCH₃), 3.78 (3H, s, OCH₃),

3.77 (3H, s, OCH₃), 2.95 (2H, t, J = 7.2 Hz, H-2), 2.53 (2H,

t, J = 8.0 Hz, H-11), 1.67–1.54 (4H, m, H-3,10), 1.29–1.27

(12H, m, H-4, 5, 6, 7, 8, 9); ¹³C NMR (CDCl₃, 100 MHz): δ

202.8 (C-1), 157.7 (C-4′), 153.6 (C-2′′), 152.9 (C-5′′), 135.1

(C-1′), 129.2 (C-2′, 6′), 122.1 (C-1′′), 119.5 (C-4′′), 114.1

(C-6′′), 113.7 (C-3′′), 113.2 (C-3′, 5′), 56.2 (OCH₃), 55.8

(OCH₃), 55.3 (OCH₃), 43.8 (C-2), 35.1 (C-11), 31.7 (C-10),

29.6 (C-6, 7, 8), 29.5 (C-5), 29.4 (C-9), 29.3 (C-4), 24.5 (C-

3); LC-MS: m/z 413.3 (M + H)⁺, 435.3 (M + Na)⁺, 451.2

(M + K)⁺; Q-Tof: m/z 413.2690 (M + H)⁺(413.2692 cal-

culated for C₂₆H₃₇O₄).

(18l) white waxy compound (325 mg, 77%); ¹H NMR

(CDCl₃, 400 MHz): δ 7.58 (1H, dd, J = 1.6, 8.4 Hz, H-6′′),

7.53 (1H, d, J = 1.6 Hz, H-2′′), 7.26 (2H, t, J = 8.0 Hz, H-

3′, 5′), 7.17 (2H, d, J = 7.2 Hz, H-2′, 6′), 7.16 (1H, t, J =

7.2 Hz, H-4′), 6.87 (1H, d, J = 8.4 Hz, H-5′′), 3.94 (3H, s,

OCH₃), 3.93 (3H, s, OCH₃), 2.91 (2H, t, J = 7.2 Hz, H-2),

2.59 (2H, t, J = 7.6 Hz, H-11), 1.75–1.68 (2H, m, H-10),

1.62–1.57 (2H, m, H-3), 1.39–1.26 (12H, m, H-4, 5, 6, 7, 8,

9); ¹³C NMR (CDCl₃, 100 MHz): δ 199.2 (C-1), 153.2 (C-

4′′), 149.1 (C-3′′), 142.9 (C-1′), 130.5 (C-1′′), 128.4 (C-3′,

5′), 128.2 (C-2′, 6′), 125.5 (C-4′), 122.6 (C-6′′), 110.3 (C-2′′),

110.0 (C-5′′), 56.0 (OCH₃), 55.9 (OCH₃), 38.2 (C-2), 35.9

(C-11), 31.5 (C-10), 29.5 (C-6, 7, 8), 29.47 (C-5), 29.40 (C-

9), 29.3 (C-4), 24.8 (C-3); LC-MS: m/z 383.3 (M + H)⁺,

405.3 (M + Na)⁺, 421.3 (M + K)⁺; Q-Tof: m/z 383.2601

(M + H)⁺(383.2586 calculated for C₂₅H₃₅O₃).

11-(3,4,5-Trimethoxyphenyl)-1-(2,5-dimethoxyphenyl)-

undecan-1-one (18m) Oily compound, (420 mg, 81%); ¹H

NMR (CDCl₃, 400 MHz): δ 7.20 (1H, d, J = 3.2 Hz, H-6′′),

6.99 (1H, dd, J = 3.2, 8.8 Hz, H-4′′), 6.89 (1H, d, J = 8.0

11-(Phenyl)-1-(2,5-dimethoxyphenyl)-undecan-1-one

(18p) White solid, (340 mg, 81%); mp 68–70 °C; ¹H

NMR (CDCl₃, 400 MHz): δ 7.26 (2H, t, J = 8.0 Hz, H-6′′),

7.21 (1H, d, J = 3.2 Hz, H-4′′), 7.16 (2H, d, J = 7.2 Hz, H-

Med Chem Res

Table 1 Biological activities of ardisinone E (15) and diarylun-

decanones

3′, 5′), 7.15 (1H, t, J = 7.2 Hz, H-2′, 6′), 6.99 (1H, dd,

J = 2.8, 8.8 Hz, H-4′), 6.88 (1H, d, J = 9.2 Hz, H-3′′), 3.84

(3H, s, OCH₃), 3.78 (3H, s, OCH₃), 2.95 (2H, t, J = 7.6 Hz,

H-2), 2.59 (2H, t, J = 7.2 Hz, H-11), 1.67–1.58 (4H, m, H-

3, 10), 1.29–1.27 (12H, m, H-4, 5, 6, 7, 8, 9); ¹³C NMR

(CDCl₃, 100 MHz): δ 202.8 (C-1), 153.6 (C-2′′), 152.8 (C-

5′′), 142.9 (C-1′), 129.2 (C-2′, 6′), 128.4 (C-3′, 5′), 128.2

(C-4′), 125.5 (C-1′′), 119.4 (C-4′′), 114.1 (C-6′′), 113.2 (C-

3′′), 56.1 (OCH₃), 55.8 (OCH₃), 43.7 (C-2), 35.9 (C-11),

31.5 (C-10), 29.5 (C-6, 7, 8), 29.48 (C-5), 29.40 (C-9), 29.3

(C-4), 24.4 (C-3); LC-MS: m/z 383.3 (M + H)⁺, 405.3 (M

+ Na)⁺; Q-Tof: m/z 383.2588 (M + H)⁺(383.2586 calcu-

lated for C₂₅H₃₅O₃).

S.No Compound

5-LOX

IC₅₀

µg/mL

Anti-oxidant

NBT(IC₅₀

µg/mL)

Brine shrimp

ED₅₀µg/mL

1

15

>100

62.10

12.80

32.03

35.54

15.23

24.60

15.23

43.35

53.51

–

56.64

18.75

12.28

50.04

18.35

11.04

12.05

11.32

>100

28.12

2.34

4.19

50.51

63.14

85.64

70.38

44.67

44.32

60.09

70.15

65.53

–

2

18c

3

18e

4

18f

5

18J

6

18k

7

18l

8

18m

9

18o

10

11

12

13

18p

5-Lipoxygenase inhibitory activity

Gallic acid

Podophyllotoxin

Curcumin

–

1.92

–

5-Lipoxygenase enzyme inhibitory activity was measured

by Schewe et al. (Schewe et al. 1986) method, which was

modiﬁed by Reddanna et al. (Reddenna et al. 1990). The

assay mixture contained 80 μM linoleic acid and potato 5-

lipoxygenase in 50 mM phosphate buffer (pH 6.3). The

reaction was initiated by the addition of enzyme buffer mix

to linoleic acid and the enzyme activity was monitored as

the increase in absorbance at 234 nm. The reaction was

monitored for 120 sec and the inhibitory potential of the test

substances 15, 18a–p were measured by incubating various

concentrations of test substances for 2 min before the

addition of linoleic acid. All assays were performed in tri-

plicate. Percentage inhibition was calculated and the results

are summarized in Table 1.

8.98

–

was used as a positive control. The results are summarized

in Table 1.

Superoxide radical scavenging activity

Superoxide radical scavenging activity of compounds 15,

18a–p was determined spectrophotometrically (560 nm) by

adopting the nitro blue tetrazolium (NBT) photo reduction

method of McCord and Fridovich (Mc Cord and Fridovich

1969). The assay mixture contained EDTA (6.6 µM), NaCN

(3 µg), riboﬂavin (2 µM), NBT (50 µM), test substance and

phosphate buffer (58 mmol, pH 7.8) in a ﬁnal volume of 3

mL. Each mixture in a tube was shaken well, and the optical

density was measured at 560 nm. Each tube was then uni-

formly illuminated with an incandescent lamp for 15 min,

and the optical density was measured again at 560 nm. The

percentage inhibition of superoxide radical-generation was

measured by comparing the absorbance values of the con-

trol and that of the test substance. The IC₅₀values were

obtained from a plot drawn between concentrations (µM)

vs. the percentage inhibition. The super-oxide radical’s

inhibitions exhibited by compounds 15, 18a–p have been

summarized in Table 1.

Brine shrimp lethality bioassay

Brine shrimp (Artemiasalina) nauplii were hatched using

brine shrimp eggs (Meyer et al. 1982) in a conical shaped

vessel (1 L), ﬁlled with sterile artiﬁcial sea water (prepared

using sea salt 38 g/L and adjusted to pH 8.5 using 1N

NaOH) under constant aeration for 48 h. After hatching, 10

nauplii were drawn through a pipette and placed in each vial

containing 4.5 mL brine solution and treated with various

concentrations of test substances and the ﬁnal volume was

made up to 5 mL using brine solution and the cultures

maintained at 37 °C for 24 h under incandescent lamps. The

surviving larvae were counted. Each experiment was con-

ducted along with control (vehicle treated), at various

concentrations of the test substance with each set containing

6 tubes and averages of the results were noted in the table.

The percentage lethality was determined by comparing the

mean surviving larvae of test and control tubes. The IC₅₀

values were obtained from the plot drawn containing con-

centration (µM) verses percentage lethality. Podophyllotoxin

Conclusion

Ardisinone E (15) a naturally occurring diarylundecanone

derivative and 16 new undecanone analogs were prepared

successfully and were characterized by their spectral data.

Ardisinone E (15) showed potent cytotoxic activity in brine

shrimp lethality assay, which could be attributable to the

Med Chem Res

Isogai A, Murakoshi S, Akinoro S, Saburo T (1973) Structures of new

dimeric phenyl propanoides from Myristica fragrans Houtt. Agric

Biol Chem 37:1479–1486

Jayaweera DMA (1982) Medicinal plants (Indigenous and Exotic)

used in Ceylon; part 4. National science council of Srilanka,

Colombo

number of hydroxyl groups present in the molecule. The

compounds 18b, 18n, 18p with more number of methoxyl

goups showed good anti-inﬂammatory activity. The com-

pounds containing hydroxyl group adjacent to the keto

functional group and also compounds with few number of

methoxy groups exhibited reasonable anti-oxidant activity.

Kumar NS, Herath HMTB, Karunaratne V (1988) Arylalkanones from

Myristica dactyloides. Phytochemistry 27:465–468

Lopes LMX, Yoshida M, Gottlieb OR (1982) 1,11-diarylundecan-1-

one and 4-aryltetralone neolignans from Virola sebifera. Phy-

tochemistry 21:751–755

Acknowledgements The authors thank Sri G. Ganga Raju, Chair-

man, Mr. G. Rama Raju, Director and Mr. B. Kiran, CEO, Laila

Nutraceuticals for their encouragement, PDT in vitro division for the

bioactivity studies.

Mc Cord JM, Fridovich I (1969) Superoxide Dismutase: An enzymatic

function for erythrocuperin. J Biol Chem 244:6049–6055

Meyer BN, Ferrigni NR, Putnam JE, Jacobsen LB, Nicols DE,

McLaughlin JL (1982) Brine shrimp: a convenient general

bioassay for active plant constituents. Planta Medica 45:31–34

Orabi KY, Mossa JS, EI-Feraly FS (1991) Isolation and character-

ization of two anti-microbial agents from mace (Myristica fra-

grans). J Nat Prod 54:856–859

Compliance with ethical standards

Conﬂict of interest The authors declare that they have no competing

interests.

Pinto MMM, Kijjoa A, Tantisewiet B, Yoshida M, Gottlieb OR (1988)

Arylalkanones from Horsﬁeldia glabra. Phytochemistry

27:3988–3989

Purushothaman KK, Sarada A, Connoly JD (1977) Malabaricones A-

D, novel diarylnonanoids from Myristica malabarica Lam

(Myristicaceae). J Chem Soc Perkin Trans 1:587–588

Reddenna P, Whelan JKRM, Reddy CC (1990) Puriﬁcation of ara-

chidonate 5-lipoxygenase from potato tubers. Methods Enzymol

187:268–277

References

Cooray NF, Jansz ER, Wimalasena S, Wijesekera TP, Nair BM (1987)

Acylresorcinol from seed kernels of Myristica dactyloides.

Pytochemistry 26:3369–3371

Denney DB, Ross ST (1962) The Preparation and Reactions of Some

Halophosphoranes. J Org Chem 27:998–1000

Forrest JE, Heacock RA, Thomas P (1974) Diarylpropanoids from

nutmeg and mace (Myristica fragrans Houtt). J Chem Soc Perkin

Trans 1:205–209

Schewe T, Rapaport SM, Kuhn H (1986) Enzymology and physiology

of reticulocyte lipoxygenase: comparison with other lipox-

ygenases. Adv Enzymol Mol Biol 58:191–272

Zheng Ying, Deng Yun, Wu Feng-E (2004) Ardisinones A-E, novel

Forrest TP, Forrest JE, Heacick RA (1970) The isolation of some

diarylpropanoids from nutmeg. Naturwissenschaften 60:257

Isogai A, Akinoro S, Saburo T (1973) Structures of dimeric phenyl

propanoides from Myristica fragrans Houtt. Agric Biol Chem

37:193–194

diarylundecanones from Ardisia arboresens.

67:1617–1619

Zahir A, Josam A, Bodas (1993) Knerachelins A and B, antibacterial

J Nat Prod

phenylacylphenols from Knema furfuracea.

56:1634–16370

J Nat Prod

Article Doi

Synthesis and biological evaluation of some undecanone derivatives

DOI: 10.1007/s00044-017-2006-7

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Article abstract of DOI:10.1007/s00044-017-2006-7

Full text of DOI:10.1007/s00044-017-2006-7

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