Synthesis and antiproliferative activity of 6,7-aryl/hetaryl coumarins

Article abstract of DOI:10.1134/S1070363216010291

Two different series of novel analogs of 6,7-aryl/hetaryl coumarins 4a-4h and 8i-8l have been synthesized by using Suzuki-Miyara cross coupling reaction from 4-methyl-2-oxo-2H-chromen-7-yl trifluoro-methanesulfonate and 4-methyl-2-oxo-2H-chromen-6-yl trifluoromethanesulfonate in high yields (70-90%). All synthesized compounds were elucidated by means of IR, ¹H NMR, ¹³C NMR, and MS spectra. The synthesized compounds were tested for antiproliferative activity against different human cancer cell lines (SiHa, MDAMB-231, and PANC-1) and some of products demonstrated the distinctive effect.

Full text of DOI:10.1134/S1070363216010291

ISSN 1070-3632, Russian Journal of General Chemistry, 2016, Vol. 86, No. 1, pp. 184–189. © Pleiades Publishing, Ltd., 2016.
Synthesis and Antiproliferative Activity
of 6,7-Aryl/Hetaryl Coumarins1
Y. Jayaprakash Raoa,b, E. Yadaiah gouda, Y. Hemasric,
Nishant Jaind, and Srujana Gabriellad
a Department of Chemistry, Osmania University, Hyderabad, Telangana, 500007 India
b Department of Chemistry, Telangana University, Nizamabad, 503322 India
c Department of Chemistry, Nizam College, Osmania University, 500001 India
d Center for Chemical Biology, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007 India
e-mail: erukalayadaiahgoud@gmail.com
Received October 14, 2015
Abstract—Two different series of novel analogs of 6,7-aryl/hetaryl coumarins 4a–4h and 8i–8l have been
synthesized by using Suzuki–Miyara cross coupling reaction from 4-methyl-2-oxo-2H-chromen-7-yl trifluoro-
methanesulfonate and 4-methyl-2-oxo-2H-chromen-6-yl trifluoromethanesulfonate in high yields (70–90%).
1
All synthesized compounds were elucidated by means of IR, H NMR, 13C NMR, and MS spectra. The
synthesized compounds were tested for antiproliferative activity against different human cancer cell lines
(SiHa, MDAMB-231, and PANC-1) and some of products demonstrated the distinctive effect.
Keywords: Suzuki coupling, pseudo halides, heteryl/aryl boronic acids, and heteryl/aryl coumarins
DOI: 10.1134/S1070363216010291
INTRODUCTION
reactive than aryl chlorides, bromides and stable under
the action of moisture and air. 7-Halo coumarins are
difficult to prepare for which reason triflate was
chosen as a synthetic precursor in the present study.
The key intermediate coumarin triflates were prepared
by a conventional method which involved treatment of
the corresponding 7-hydroxy-4-methyl-coumarine (2,
4) with triflic anhydride in the presence of tri-
ethylamine. Jean-Thomas [14] reported the synthesis
of 4-substituted coumarins by palladium catalyzed
cross-coupling reactions of 4-tosyl coumarins. We
reported a synthetic approach to new aryl/hetero-
arylated coumarins by using Suzuki-Miyara cross
coupling reaction of triflate with 4-methyl-7-hydroxy
coumarin (Schemes 1, 2).
Currently there is a huge demand in potent, safe
and selective anticancer drugs because cancer is
predicted to be the primary cause of death in future
[1, 2].
Coumarins demonstrate important biological
functions in nature and have been recognized as
pharmacophores of a large number of bioactive
molecules of either natural or synthetic origin. Over
recent years they attracted attention due to their diverse
pharmacological properties such as anti-HIV [3],
anticoagulant [4], antibacterial [5], antioxidant [6],
anti-inflammatory [7, 8], antimicrobial [9], anticancer
[10], chemoprophylactic [11] and dyslipidemic [12].
Cytotoxic effects of coumarins were extensively
studied [13].
Synthesis of 6,7-hydroxy-4-methyl coumarin deriva-
tives was performed according to the von Pechmann
reaction with minor modifications depending on the
stability and reactivity of the used reagents [15]. Com-
pound 2 was obtained by condensing resorcinol and
ethyl acetoacetate under the action of a large excess of
concentrated sulfuric acid. 6,7-Trifluoromethylsulfonyl-
oxycoumarins were easily prepared in 73–97% yield
by treatment of the appropriate 6,7-hydroxy-4-methyl
coumarins with triflic anhydride [16]. The reaction of
The aim of the present study was to develop simple
and efficient procedure for preparation of new
coumarin derivatives bearing substituted heteryl and
aryl moieties by the Suzuki cross coupling reaction.
Aryl triflates are efficient leaving groups, more
1 The text was submitted by the authors in English.
184

SYNTHESIS AND ANTIPROLIFERATIVE ACTIVITY OF 6,7-ARYL/HETARYL COUMARINS
185
Scheme 1. Synthesis of 7-(aryl and heteryl)-4-methyl coumarins.
O
F3C
HO
O
O
R
O
O
S
O
O
HO
OH
c
a
b
O
1
2
3
4a−4h
R = Ar/HAr. Reagents and conditions: a: H2SO4, ethylacetoacetate, 15 min; b: Et3N, Tf2O, DCM, 1 h; c: RB(OH)2, Pd(PPh3)4,
K2CO3, DMF, 2–4 h.
triflate with two equivalents of various aryl boronic
acids afforded the 6,7-aryl/heteroaryl coumarins in 70–
85% yield [14, 16, 17]. The yields of the products
derived from electron rich boronic acids were higher
than those derived from electron poor boronic acids.
1H NMR spectra of products demonstrated absence of
OH protons and presence of couamrin protons at (δ,
ppm): 7.53 d (1H, 5-H, J = 8.7 Hz), 7.55 s (1H, 8-H),
7.65 d (1H, 6-H, J = 8.7 Hz), 2.49 d (4-CH3) and in its
DIPMS [M + H] was registered at 309 indicating that
triflation had taken place. The Suzuki cross coupling
reaction was tried with coumarin-triflates 3 and 5 with
different boronic acids. Aryl triflates were sensitive to
strong bases that facilitated the further procedure with
formation of dimmers for which reason potassium
carbonate was used in the process. The reaction of
coumarin triflate with boronic acids in the presence of
Pd(PPh3)4 and potassium carbonate in dimethyl
formamide under mild conditions afforded the
corresponding hetaryl and aryl coumarins 4a–4h, 8i–8l
in moderate to high yields (Table 1).
EXPERIMENTAL
All chemicals were purchased from Aldrich and
Merk. Melting points were measured in open capillary
tubes. The IR spectra were recorded as KBr pellets
1
with a Shimadzu FT-IR-8400s spectrophotometer. H
NMR (400 MHz) and 13C NMR (100 MHz) spectra
were measured with Bruker Avance II 400 spectro-
meter using TMS as an internal standard in CDCl3
solution. Mass spectra were measured with a Hewlett-
Packard 1100 LC/MSD spectrometer.
Synthesis of 7-(aryl and heteryl)-2,3-dimethyl-4-
coumarins (4a–4l). Coumarin triflate 4 (0.8 mmol,
1.0 equiv.), boronic acids (1.5 equiv) and K2CO3 (1 mL
of 2 mol of aqueous solution) in DMF was purged
with N2 upon stirring for 30 min. Tetrakis(triphenyl-
phosphine)palladium(0) (4 mol %) was added to the
reaction mixture and purged with nitrogen for 30 min
followed by stirring at 90°C for 2–4 h. Upon com-
pletion of the reaction, the mixture was cooled down to
room temperature and diluted with water (50 mL),
extracted with diethylether (3 × 30 mL). The extracts
were dried over Na2SO4 and concentrated under
reduced pressure. The crude products 4a–4h and 8i–8l
were purified by column chromatography.
Antiproliferative activity. The prepared 6,7-aryl/
heteroaryl coumarins (4a–4h, 8i–8l) were evaluated
for antiproliferative activity against a panel of three
different human tumor cells from cervix (SiHa), brest
(MDA-MB-231) and pancreatic carcinoma (PANC-1,
SIHA, MDA-MB-231 and PANC-1) cell lines obtained
from American Type Culture Collection using the
sulforhodamine B (SRB) assay method. CA-4 was
used as a standard drug (Table 2).
4-Methyl-7-(21,31-dimethylphenyl)-2H-chromen-
2-one (4a). mp 97ºC, yield 85%. IR spectrum (KBr), ν,
cm–1: 1716.0 (C=O) (1613 C=C), 2925 (C–H). H
1
NMR spectrum, δ, ppm: 2.34 s (3H, CH3), 2.36 s (3H,
CH3), 2.47 d (3H, CH3, J = 1.0 Hz), 6.30 d (1H, 3-H,
J = 1.0 Hz), 7.24 d (1H, 61-H), 7.40 d.d (1H, 51-H, 8.4,
1.6 Hz), 7.42 d (1H, 41-H , J = 8.7 Hz), 7.53 d (1H,
5-H, J = 8.7 Hz), 7.55 s (1H, 8-H), 7.65 d (1H, 6-H,
J = 8.7 Hz). 13C NMR spectrum, δ, ppm: 20.0, 19.2,
18.5 (CH3), 114.4, 114.6, 118.5, 122.9, 124.5, 124.8,
128.6, 130.7, 136.5, 137.3, 137.4, 145.1, 152.1, 154.0,
161.1 (C=O). C18H16O2. Mass spectrum (ESI): m/z 265
[M + H]+.
According to the tests data (Table 2) compounds
4a–4h and 8a–8d possessed antiproliferative activity
against the cell lines in the concentration dependent
manner and were found to be moderate to highly
active. It should be pointed out that the compounds 4b
and 4a exhibited broad spectrum of antiproliferative
activity. The selective activity was demonstrated by 4h
and 8c on MDA-MB-231 and SiHa cell lines and by 4c
and 8d on SiHa and MDA-MB-231 cell lines.
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186
Y. JAYAPRAKASH RAO et al.
Scheme 2. Synthesis of 6-(aryl and heteryl)-4-methyle coumarins.
OH
O
O
O
O
O
O
a
b
c
O
S
HO
R
F3C
O
OH
5
6
7
8i−8l
31
21
11
O
N
O
Br
41
51
1
O
8
O
O
9
O
O
O
7
61
2
3
6
10
4
5
4a
4b
4c
F
Cl
F
NC
O
O
O
O
O
O
4d
4e
4f
31
211
21
CHO
41
51
311
1
111
7
8
O
O
2
3
11
O
O
61
6
4
5
4g
4h
O
O
O
O
N
O
N
O
8i
8j
O
O
O
O
OHC
O
8k
8l
R = Ar/HAr. Reagents and conditions: a: H2SO4, EAA, CHCl3, 6 h; b: Et3N, Tf2O, DCM, 1 h; c: RB(OH)2, Pd(PPh3)4,
K2CO3, DMF, 2–4 h.
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SYNTHESIS AND ANTIPROLIFERATIVE ACTIVITY OF 6,7-ARYL/HETARYL COUMARINS
187
Table 1. Synthesis of 6- and 7-aryl/hetaryl coumarins 4a–4h and 8i–8l
Comp.
no.a
Comp.
no.a
R = Ar/Ht
Timeb, h Yield, %
R = Ar/Ht
Timeb, h Yield, %
4a
2
85
4g
2
85
OH
B
OH
B
OH
OH
OH
OH
B
4b
4c
2
2
80
80
4h
8i
4
3
70
B
OHC
N
OH
OH
O
O
OH
75
Br OH
B
B
OH
OH
N
O
OH
B
OH
B
4d
4e
2
4
90
70
8j
2
3
80
70
OH
N
OH
Cl
O
OH
B
OH
B
8k
OHC
OH
OH
NC
F
F
OH
B
OH
4f
3
70
8l
2
80
B
OH
OH
O
a 4a–4h and 8i–8l were characterized by IR, 1H NMR, 13C NMR and MS. b The reaction was completed at the indicated time.
7-(61-Methoxypyridin-3-yl)-4-methyl-2H-chromen-
2-one (4b). mp 141°C, yield 80%. IR spectrum (KBr),
trum, δ, ppm: 2.46 s (3H, CH3), 4.0 s (3H, OCH3), 6.30
d (1H, 3-H), 7.14 s (1H, 8-H), 7.21 s (2H, 31,51-H,),
7.41 d.d (1H, 61-H, J = 8.0, 1.6 Hz), 7.50 d (1H, 5-H,
J = 8.553 Hz), 7.61 d (1H, 6-H, J =8.031 Hz). 13C
NMR spectrum, δ, ppm: 18.6, 53.8 (OCH3), 112.4,
113.6, 118.1, 118.6, 120.1, 121.5, 124.1, 127.2, 128.1,
131.0, 136.2, 150.7, 152.3, 161.71, 162.9 (C=O).
C17H13BrO3. Mass spectrum: m/z 346 [M + H]+.
1
ν, cm–1: 1716.0 (C=O). H NMR spectrum, δ, ppm:
2.47 d (3H, CH3, J = 1.004 Hz), 4.0 s (3H, OCH3),
6.30 d (1H, 3-H, J = 1.004 Hz), 6.88 d (1H, 61-H), 7.49
d (1H, 51-H, J =8.78 Hz), 7.50 s (1H, 8-H), 7.69 d (1H,
5-H, J = 8.78 Hz), 7.88 d.d (1H, 11-H, J = 8.4, 1.6 Hz),
7.46 d (1H, 61-H, J = 8.78 Hz). 13C NMR spectrum, δ,
ppm: 18.6, 53.7, 111.3, 114.5, 114.9, 118.9, 122.4,
125.20, 128.1, 132.3, 141.60, 145.3, 152.3, 154.10,
160.71, 164.3 (C=O). C18H16NO2. Mass spectrum
(ESI): m/z 268 [M + H]+.
7-(41-Chlorophenyl)-4-methyl-2H-chromen-2-
one (4d). mp 135°C, yield 90%. IR spectrum (KBr), ν,
1
cm–1: 1638.0 (C=O), 737 (C–Cl), 1078 (C–O–C). H
NMR spectrum, δ, ppm: 2.49 d (3H, CH3, J = 1.25 Hz),
6.32 d (1H, 3-H, J = 1.25 Hz), 7.45 s (1H, 8-H), 7.46 d
(1H, 5-H, J = 8.031 Hz), 7.53 d (1H, 31,51-H, J =
8.031 Hz), 7.55 d (1H, 21,61-H, J = 1.77 Hz), 7.46 d
7-(21-Bromo-41-methoxyphenyl)-4-methyl-2H-
chromen-2-one (4c). mp 175°C, yield 80%. IR spec-
1
trum (KBr), ν, cm–1: 1638.0 (C=O). H NMR spec-
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 1 2016

188
Y. JAYAPRAKASH RAO et al.
4-Methyl-7-(21,31-difulorolphenyl)-2H-chromen-
2-one (4f). mp 115–120°C, yield 70%. IR spectrum
Table 2. Antiproliferative activity of 6,7-aryl/heteroaryl
coumarins 4a–4h and 8i–8l on SiHa, MDA-MB-231, and
PANC-1 human cancer cellsa
1
(KBr), ν, cm–1: 1638.0 (C=O). H NMR spectrum, δ,
GI50, µMb
MDAMB-231
0.296 ±0.01 0.5 ±0.07
ppm: 2.34 (3H, CH3), 2.36 s (3H, CH3), 2.47 d (3H,
CH3, J = 1.004 Hz), 6.30 d (1H, 3-H, J = 1.004 Hz),
6.24 s (1H, 61-H), 7.40 d.d (1H, 51-H, J = 8.7, 1.5 Hz),
7.42 d (1H, 41-H, J = 8.78 Hz), 7.53 d (1H, 5-H, J =
8.00 Hz), 7.55 s (1H, 8-H), 7.65 d (1H, 6-H, J =
8.78 Hz). 13C NMR spectrum, δ, ppm: 18.5, 114.4, 114.6,
118.5, 122.9, 124.5, 124.8, 128.6, 130.7, 136.5, 137.3,
137.4, 145.1, 152.1, 154.0, 161.1 (C=O). C16H10F2O2.
Mass spectrum: m/z 273 [M + H]+.
Entrya
SIHA
PANC-1
4a
4b
0.5 ±0.04
0.16 ±0.04 0.115 ±0.03 0.12 ±0.02
4c
0.65 ±0.01 0.523 ±0.02 2 ±0.08
4d
4e
4f
0.811 ±0.01 0.856 ±0.02 0.971 ±0.07
0.436 ±0.08 0.745 ±0.07 0.849 ±0.07
0.985 ±0.05 0.435 ±0.08 0.9 ±0.02
3-(4-Methyl-2-oxo-2H-chromen-7-yl)benzaldehyde
(4g). mp 205–215°C, yield 85%. IR spectrum (KBr), ν,
1
cm–1: 1765.0 (C=O), 1745 (CH=O). H NMR spec-
trum, δ, ppm: 2.48 d (3H, CH3, J = 1.004 Hz), 6.30 d
(1H, 3-H, J = 1.004 Hz), 7.15 d.d (2H, 5,6-H, J =
8.78 Hz), 7.55 s (1H, 8-H), 7.48 m (3H, 415161-H),
9.10 s (1H, CHO). 13C NMR spectrum, δ, ppm: 18.5,
114.6, 121.6, 122.9, 124.5, 127.8, 128.6, 130.7, 136.5,
137.3, 136.4, 147.1, 150.1, 159.0, 162.1 (C=O), 195.6
(CHO). C16H2O3. Mass spectrum: m/z 265 [M + H]+.
4g
4h
0.588 ±0.07 0.664 ±0.01 0.8 ±0.04
0.782 ±0.03 0.191 ±0.03 0.836 ±0.01
8i
8j
0.695 ±0.05 0.879 ±0.04 0.774 ±0.03
8.834 ±0.09 7.436 ±0.08 9.392 ±0.08
8-Allyl-4-methyl-7-phenyl-2H-chromen-2-one
(4h). mp 95°C, yield 70%. IR spectrum (KBr), ν, cm–1:
1638.0 (C=O). 1H NMR spectrum, δ, ppm: 2.49 d (3H,
CH3, J = 1.255 Hz), 3.5 d (2H, 111-H, J = 5.77 Hz),
4.83 d (1H, 311-H, J = 18.823 Hz), 5.1 d (1H, 311-H,
J = 11.544 Hz), 6.01 m (1H, 211-H) 6.32 d (1H, 3-H,
J = 1.555 Hz), 7.42 m (5H), 7.53 d (1H, 5-H, J =
2.008 Hz), 7.65 d (1H, 6-H, J = 8.284 Hz). 13C NMR
spectrum, δ, ppm: 18.6, 28.6, 98, 114.4, 114.6, 115,
118.5, 122.9, 124.5, 124.8, 128.6, 130.7, 136.5, 137.3,
137.4, 145.1, 152.1, 154.0, 161.1 (C=O). C19H16O2.
Mass spectrum: m/z 277 [M + H]+.
8k
8l
0.147 ±0.06 3.516 ±0.04 0.9 ±0.05
0.275 ±0.05 4.999 ±0.06 1 ±0.03
Combretastatin <0.01
(CA4)
0.024 ±0.001 0.016 ±0.002
a
Cell lines were treated with different concentration of
compounds for 48 h. Cell viability was measured employing SRB
assay. b GI50 values (in µM) are indicated as mean ±SD of three
independent experiments.
4-Methyl-6-(41-morpholinophenyl)-2H-chromen-
2-one (4i). mp 140°C, yield 70%. IR spectrum (KBr),
(1H, 6-H, J = 8.031 Hz). 13C NMR spectrum, δ, ppm:
18.6, 115.5, 119.3, 123.3, 123.5, 125.4, 128.4, 129.5, 134.5,
137.5, 143.5, 152.2, 154.0, 160.9 (C=O). C16H11ClO2.
Mass spectrum: m/z 271 [M + H]+.
1
ν, cm–1: 1638.0 (C=O). H NMR spectrum, δ, ppm:
2.48 d (3H, CH3, J = 1.255 Hz), 3.2 t (4H, 211-H, J =
4.768 Hz), 3.9 t (4H, 311-H, J = 4.768 Hz), 6.32 d (1H,
3-H, J = 1.004 Hz), 7.0 d (2H, 21,61-H, J = 8.78 Hz),
7.4 s (1H, 5-H), 7.5 d (1H, 31,51-H, J = 9.075 Hz), 7.9
d (2H, 7,8-H, m). 13C NMR spectrum, δ, ppm: 18.8, 49.0,
66.8,115, 115.2, 115.8, 117.4, 122, 127.8, 131, 137.2,
150, 150.9, 160.9 (C=O). C20H19NO3. Mass spectrum:
m/z 322 [M + H]+.
4-(4-Methyl-2-oxo-2H-chromen-7-yl)benzonitrile
(4e). mp 178°C, yield 70%. IR spectrum (KBr), ν, cm–1:
1
1635.0 (C=O); 2212.0 (CN). H NMR spectrum, δ,
ppm: 2.50 d (3H, CH3, J = 1.004 Hz), 6.32 d (1H, 3-H,
J = 1.004 Hz), 7.45 d (1H, 31,51-H), 7.6 s (1H, 8-H),
7.53 d (1H, 5-H, J = 8.78 Hz), 7.55 d (1H, 6-H, J =
13
8.78 Hz), 7.88 d (1H, 21,61-H, J = 9.78 Hz). C NMR
6-(6-Methoxypyridin-3-yl)-4-methyl-2H-chromen-
2-one (4j). mp 139ºC, yield 70%. IR spectrum (KBr),
spectrum, δ, ppm: 18.6, 103, 113.5, 115.3, 115.6, 123.5,
125.4, 125.8, 128, 132.9, 143.3, 152, 153.8, 155.2,
161.2, 161.6 (C=O). C17H11NO2. Mass spectrum: m/z
262 [M + H]+.
1
ν, cm–1: 1638.0 (C=O). H NMR spectrum, δ, ppm:
2.47 d (3H, CH3, J = 1.255 Hz), 4.0 s (3H, OCH3),
6.30 d (1H, 3-H, J = 1.004 Hz), 6.88 d (1H, 61-H, J =
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SYNTHESIS AND ANTIPROLIFERATIVE ACTIVITY OF 6,7-ARYL/HETARYL COUMARINS
189
8.784 Hz), 7.39 d (1H, 51-H, J = 8.78 Hz), 7.50 s (1H,
8-H), 7.69 d (1H, 5-H, J = 8.78 Hz), 7.46 d (1H, 61-H,
J = 8.78 Hz,) 7.88 d.d (1H, 11-H, J = 10.78 Hz). 13C
NMR spectrum, δ, ppm: 18.6, 53.7, 111.3, 114.5, 114.9,
118.9, 122.4, 125.20, 128.1, 132.3, 141.60, 145.3,
152.3, 154.10, 160.71, 164.3 (C=O). C18H16NO2. Mass
spectrum: m/z 268 [M + H]+.
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3-(4-Methyl-2-oxo-2H-chromen-6-yl)benzaldehyde
(4k). mp 220°C, yield 70%. IR spectrum (KBr), ν, cm–1:
1765.0 (C=O). 1H NMR spectrum, δ, ppm: 2.49 d (3H,
CH3, J = 1.004 Hz), 6.32 d (1H, 3-H, J = 1.004 Hz),
7.15 d.d (2H, 7, 8-H, J = 8.4, 1.6 Hz), 7.55 s (1H,
5-H), 7.48 m (3H, 415161-H), 9.10 s (1H, CHO). 13C
NMR spectrum, δ, ppm: 18.5, 114.6, 121.6, 122.9, 124.5,
127.8, 128.6, 130.7, 136.5, 137.3, 137.4, 145.1, 152.1,
154.0, 161.1 (C=O), 195.6 (CHO). C16H2O3. Mass spec-
trum: m/z 265 [M + H]+.
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Med. Chem. Lett., 2004, vol.14, p. 611.
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6-(41-Methoxy-21-methylphenyl)-4-methyl-2H-
chromen-2-one (4l). mp 131°C, yield 85%. IR spec-
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1
trum (KBr), ν, cm–1: 1638.0 (C=O). H NMR spec-
trum, δ, ppm: 2.30 s (3H, 31-CH3), 2.48 d (3H, 3-CH3,
J = 1.255 Hz), 3.85 s (3H, OCH3), 6.32 d (1H, 3-H, J =
1.004 Hz), 6.85 s (1H, 31-H), 7.16 d (1H, 51-H, J =
8.031 Hz), 7.25 s (1H, 5-H), 7.27 d (1H, 61-H, J =
8.78 Hz), 7.30 d (1H, 8-H, J = 8.282 Hz), 7.62 d (1H,
7-H, J = 8.282 Hz). 13C NMR spectrum, δ, ppm: 18.6,
20.79, 55.3, 111.5, 114.7, 116.1, 117.7, 118.3, 124.1, 125.7,
130.8, 132.6, 136.7, 145.8, 152.3, 153.4, 159.4, 161.0
(C=O). C18H16O3. Mass spectrum: m/z 281 [M + H]+.
ACKNOWLEDGMENTS
The authors are thankful to the Head, Department
of Chemistry, Osmania University, Hyderabad, for
providing Laboratory facilities and the Director,
CFRD, Osmania University, Hyderabad, for providing
spectral analysis facilities. Erukala Yadaiah Goud, is
thankful to CSIR, New Delhi, India, for financial
support in the form of CSIR-SRF.
REFERENCES
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2. Varmus, H., Science, 2006, vol. 312, p. 1162.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 1 2016