Cyclization of α,α′-bis(substituted-benzylidene) cyclohexanones and 4-hydroxycoumarin: Synthesis of 11-benzylidene-8,9,10,11- tetrahydro-7-phenyl-6H,7H-chromeno[4,3-b]chromen-6-ones as new pyranochromene derivatives

Article abstract of DOI:10.1007/s00706-012-0845-y

A series of new 11-benzylidene-8,9,10,11-tetrahydro-7-phenyl-6H,7H- chromeno[4,3-b]chromen-6-ones has been synthesized through a new Michael addition domino cyclization between α,α′-bis(substituted- benzylidene)cyclohexanones and 4-hydroxycoumarin in acetic acid at reflux conditions. Very good to excellent yields of the products, operational simplicity, and simple workup are attractive features of this synthesis protocol.

Full text of DOI:10.1007/s00706-012-0845-y

Monatsh Chem (2013) 144:415–419
DOI 10.1007/s00706-012-0845-y
ORIGINAL PAPER
Cyclization of a,a0-bis(substituted-benzylidene)cyclohexanones
and 4-hydroxycoumarin: synthesis of 11-benzylidene-8,9,10,11-
tetrahydro-7-phenyl-6H,7H-chromeno[4,3-b]chromen-6-ones
as new pyranochromene derivatives
•
Gholam Hossein Mahdavinia Somayyeh Peikarporsan
Received: 7 January 2012 / Accepted: 19 August 2012 / Published online: 15 September 2012
Ó Springer-Verlag 2012
Abstract A series of new 11-benzylidene-8,9,10,11-tet-
rahydro-7-phenyl-6H,7H-chromeno[4,3-b]chromen-6-ones
has been synthesized through a new Michael addition
domino cyclization between a,a0-bis(substituted-benzyli-
dene)cyclohexanones and 4-hydroxycoumarin in acetic
acid at reflux conditions. Very good to excellent yields of
the products, operational simplicity, and simple workup are
attractive features of this synthesis protocol.
Coumarin derivatives are widespread in nature and are
reported to have various biological activities [12, 13], such
as anti-HIV, antibiotic, antifungal, antibacterial, antiviral,
anticlotting, and especially anticoagulant and cytotoxic,
and they have attracted attention for producing anti-cancer
medicines [14–18].
a,a0-Bis(benzylidene)cycloalkanones have attractive
biological activities such as decreasing cholesterol, quinine
reductase induction, cytotoxic effects, cure of heart dis-
eases, use as anti-cancer agents, antioxidant, and inhibition
of HIV integrase [19–24].
Keywords Cyclizations ꢀ Pyranochromene ꢀ HIV ꢀ
Michael addition ꢀ a,a0-Bis(substituted-benzylidene)-
cyclohexanones ꢀ 4-Hydroxycoumarin
Because of the biological potential of the three groups of
above-described compounds and in continuation of our
studies toward heterocyclic synthesis [25, 26], we herein
wish to report the synthesis of 11-benzylidene-8,9,10,11-
tetrahydro-7-phenyl-6H,7H-chromeno[4,3-b]chromen-6-ones
as new pyranochromene derivatives. Recently, several meth-
ods have been reported for synthesizing coumarin derivatives
because of their numerous biological and industrial properties
[27–29]. Among them, the Michael addition of 4-hydroxy-
coumarin to a,b-unsaturated systems has become a very
attractive methodology in recent years [30–34]. Most of the
methods have their own merits. To the best of our knowledge,
there are no reports on the Michael addition of 4-hydroxy-
coumarin and a,a0-bis(substituted-benzylidene)cycloalka-
none compounds to provide a novel series of coumarin
derivatives.
Introduction
The pyran nucleus has long been recognized as an impor-
tant component of biological and pharmacological activity
in various types of natural products and their synthetic
analogs, such as spasmolytic, diuretic, anticoagulant, anti-
cancer, and antianaphylactic activities [1]. Pyrans are also
useful as photochromic materials [2–6] and occur in vari-
ous natural products [7–11]. Therefore, this skeleton is
widely seen as an important scaffold in bioorganic and
medicinal chemistry, and many pyran-containing mole-
cules are found in drugs and agrochemicals.
G. H. Mahdavinia (&)
Department of Chemistry Marvdasht Branch,
Islamic Azad University, Marvdasht, Iran
e-mail: hmahdavinia@gmail.com
Results and discussion
Treatment of 4-hydroxycoumarin (2) with 1 equivalent of
a,a0-bis(substituted-benzylidene)cyclohexanones 1 in acetic
acid at 130 °C resulted in the corresponding 11-benzylidene-
S. Peikarporsan
Department of Chemistry, Firoozabad Branch,
Islamic Azad University, Fars, Iran
123

416
G. H. Mahdavinia, S. Peikarporsan
Scheme 1
Table 1 Synthetic results of 3c under different reaction conditions
Initial studies to optimize the reaction conditions indi-
cated that the best solvent for this reaction was acetic acid
with heating at reflux temperature. Reaction of 4-hy-
droxycoumarin and a,a0-bis(benzylidene)cyclohexanones 1
in glacial acetic acid for the appropriate time will produce
11-benzylidene-8,9,10,11-tetrahydro-7-phenyl-6H,7H-chro-
meno[4,3-b]chromen-6-ones 3.
Entry Solvent Catalyst Temperature/°C
Time/h Yield/%
1
2
EtOH
EtOH
EtOH
EtOH
EtOH
–
Room temperature 12
Reflux 10
Room temperature 12
0
–
Ic/65
0
3
PTSA
PTSA
PTSA
4
50
12
5
Trace
Ic/87
Ic/70
Ic/90
Trace
20
A series of a,a0-bis(benzylidene)cyclohexanones was
selected to undergo the condensation reaction. As shown in
Table 2, it seems that the effect of substituted groups on the
aromatic ring of a,a0-bis(benzylidene)cyclohexanones is sig-
nificant; electron-withdrawing groups such as nitro and halide
give better yields than electron-donating groups such as
methyl and methoxy (in the latter case no product could be
isolated). All products in Table 2 are new compounds.
This reaction was examined with other a,a0-bis(ben-
zylidene)cycloalkanones such as cyclopentanone and
cycloheptanone, but they did not give any suitable results.
In summary, we have accomplished a simple and effi-
cient route for the one-pot synthesis of 11-benzylidene-
8,9,10,11-tetrahydro-7-phenyl-6H,7H-chromeno[4,3-b]chro-
men-6-ones in very good yields. Particularly prominent
features of this method include the operational simplicity,
clean reaction profiles, inexpensive starting materials, cata-
lyst-free protocol, and increased safety for small-scale high-
speed synthesis. Furthermore, this series of new compounds
may provide a new class of biologically active compounds.
5
Reflux
Reflux
130
6
CH3CN PTSA
12
1
7
–
–
–
–
–
–
8
AcOH
AcOH
AcOH
AcOH
Room temperature 12
9
50
12
3
10
11
130
130
Ic/90
90
6
8,9,10,11-tetrahydro-7-phenyl-6H,7H-chromeno[4,3-b]chro-
men-6-one derivatives 3a–3i in high yields (Scheme 1).
Using the conversion of 4-hydroxycoumarin and a,
a0-bis(4-chlorobenzylidene)cyclohexanone (1c) as a model,
several parameters were explored, as shown in Table 1.
The yield of 3c was low in ethanol or acetonitrile as a
solvent (Table 1, entries 1-6), and much greater in acetic
acid as solvent, reaching a maximum of 90 % yield at
reflux condition in acetic acid (Table 1, entry 11). The
yield of 3c was also dependent on temperature (entries 9,
11). Formation of 3c was dependent on time (entries 10,
11); when time was decreased, intermediate I was formed
and isolated (entry 10). After completion of the reaction
(monitored by TLC), the mixture was cooled, and the
resulting solid product was collected by filtration.
Experimental
It seems that the most common way to synthesize pyr-
anochromenes 3 is interaction of 4-hydroxycoumarin and
a,a0-bis(benzylidene)cyclohexanones 1, and for enclosing
the ring, we tried to complete this reaction in acidic con-
ditions with acetic acid as a solvent. This reaction had
satisfactory results because the acidic environment pro-
vided the best conditions for ring closing and making 4H-
pyran rings. Although we have not established the mech-
anism of reaction experimentally, the reaction is thought to
proceed via the Michael addition of active methylene
4-hydroxycoumarin onto a,a0-bis(benzylidene)cycloalka-
nones, which affords intermediate I followed by the
intramolecular dehydration of intermediate I as depicted
in Scheme 2.
Economic and empirical synthesis of a,a0-bis(benzyli-
dene)cycloalkanones 1 as a precursor by aldol conden-
sation of cycloalkanones with substituted aromatic aldehydes
with use of ethanolic KOH had many good results [35].
Other chemicals were purchased from Merck or Aldrich
and were used without further purification. Melting points
were measured on an Electrothermal 9200 apparatus. IR
spectra were recorded as KBr pellets on an FT-IR spec-
1
trometer. H NMR (400 MHz) and 13C NMR (100 MHz)
spectra were obtained using a Bruker DRX-400 spec-
trometer from solutions in CDCl3. Chemical shifts are
reported in parts per million (d) downfield from an internal
TMS reference, coupling constants (J values) are reported
123

Cyclization of a,a0-bis(substituted-benzylidene)cyclohexanones and 4-hydroxycoumarin
417
Scheme 2
Table 2 Synthesis of 11-benzylidene-8,9,10,11-tetrahydro-7-phe-
nyl-6H,7H-chromeno[4,3-b]chromen-6-ones
7.58 (m, 1H, ArH), 7.31–7.46 (m, 13H, ArH, CH=), 4.46
(s, 1H, CH–Ar), 2.84 (m, 1H, CH of CH2), 2.70 (m, 1H,
CH of CH2), 2.20 (m, 2H, CH2), 1.74 (m, 2H, CH2) ppm;
13C NMR (100 MHz, CDCl3): d = 161.6 (C=O), 155.1,
152.7, 142.4, 141.9, 137.1, 131.8, 130.1, 129.3, 128.6,
128.5, 128.2, 127.2, 126.9, 124.1, 122.9, 122.7, 117.4,
116.8, 114.7, 103.7, 41.5 (CH), 27.7 (CH2), 27.2 (CH2),
Entry
Ar
Product
Yield/%a
M.p./°C
1
2
3
4
5
6
7
8
9
a
C6H5
3a
3b
3c
3d
3e
3f
80
80
90
85
85
90
85
95
80
265–267
205–207
280–282
218–219
267–268
288–290
295–297
274–276
239–242
2-ClC6H4
4-ClC6H4
4-MeC6H4
3-NO2C6H4
4-NO2C6H4
4-BrC6H4
4-CNC6H4
2-Naphthyl
ꢀ
22.4 (CH2) ppm; IR (KBr): m = 3,070 (CH arom), 2,922
(CH aliph), 2,852 (CH aliph), 1,713 (C=O), 1,668 (C=C),
1,626 (C=C), 1,491 (C=C), 1,455, 1,395 cm-1
.
3g
3h
3i
11-(2-Chlorobenzylidene)-7-(2-chlorophenyl)-8,9,10,11-
tetrahydro-6H,7H-chromeno[4,3-b]chromen-6-one
(3b, C29H20Cl2O3)
Isolated yields after 6 h
Yield 80 %; m.p.: 205–207 °C; 1H NMR (400 MHz,
CDCl3): d = 8.04 (dd, J = 7.8 Hz, 1.6 Hz, 1H, ArH),
7.60 (m, 1H, ArH), 7.18–7.50 (m, 11H, ArH, CH=), 5.12
(s, 1H, CH–Ar), 2.70 (m, 1H, CH of CH2), 2.53 (m, 1H,
CH of CH2), 2.32 (m, 1H, CH of CH2), 2.11 (m, 1H, CH of
CH2), 1.70 (m, 2H, CH2) ppm; 13C NMR (100 MHz,
CDCl3): d = 161.2 (C=O), 155.8, 152.8, 141.3, 140.2,
135.3, 134.2, 134.0, 132.0, 131.3, 130.6, 130.5, 129.6,
129.5, 128.3, 127.3, 126.3, 124.2, 122.7, 120.2, 117.6,
116.8, 114.5, 102.6, 37.1 (CH), 27.2 (CH2), 27.7 (CH2),
in hertz (Hz), and spin multiplicities are indicated by the
following symbols: s (singlet), d (doublet), t (triplet), and m
(multiplet). Mass spectra were recorded with an Agilent
mass spectrometer at an ionization voltage of 70 eV.
General procedure for the synthesis
of chromenochromenes
A mixture of 0.162 g 4-hydroxycoumarin (1.0 mmol), the
a,a0-bis(substituted-benzylidene)cycloalkanone (1.0 mmol),
and 5.0 cm3 glacial acetic acid was stirred and refluxed in
an oil bath at 130 °C for 6 h. After completion of the
reaction, the mixture was kept at room temperature, and the
resulting product was collected by filtration and washed
with cold ethanol. The product was found to be pure, and
no further purification was necessary.
ꢀ
22.1 (CH2) ppm; IR (KBr): m = 3,085 (CH arom), 2,924
(CH aliph), 2,845 (CH aliph), 1,721 (C=O), 1,672, 1,630
(C=C), 1,462 (C=C), 1,436 (C=C), 1,378, 1,032, 764
(C–Cl), 740 cm-1
.
11-(4-Chlorobenzylidene)-7-(4-chlorophenyl)-8,9,10,11-
tetrahydro-6H,7H-chromeno[4,3-b]chromen-6-one
(3c, C29H20Cl2O3)
Yield 90 %; m.p.: 280–282 °C; 1H NMR (400 MHz,
CDCl3): d = 8.00 (dd, J = 8.0 Hz, 1.2 Hz, 1H, ArH),
7.59 (m, 1H, ArH), 7.29–7.42 (m, 11H, ArH), 7.18 (s, 1H,
CH=), 4.43 (s, 1H, CH–Ar), 2.79 (m, 1H, CH of CH2), 2.65
11-Benzylidene-8,9,10,11-tetrahydro-7-phenyl-6H,7H-
chromeno[4,3-b]chromen-6-one (3a, C29H22O3)
Yield 80 %; m.p.: 265–267 °C; 1H NMR (400 MHz,
CDCl3): d = 8.03 (dd, J = 7.8 Hz, 1.2 Hz, 1H, ArH),
123

418
G. H. Mahdavinia, S. Peikarporsan
(m, 1H, CH of CH2), 2.16 (m, 2H, CH2), 1.73 (m, 2H, CH2)
ppm; 13C NMR (100 MHz, CDCl3): d = 161.5 (C=O),
155.1, 152.7, 141.9, 140.8, 135.4, 133.1, 132.7, 132.0,
130.6, 130.5, 129.9, 128.7, 128.4, 124.2, 122.6, 122.0,
117.3, 116.9, 114.5, 103.2, 40.9 (CH), 27.6 (CH2), 27.1
1H, CH of CH2), 2.66 (m, 1H, CH of CH2), 2.26 (m, 1H,
CH of CH2), 2.12 (m, 1H, CH of CH2), 1.79 (m, 2H, CH2)
ppm; 13C NMR (100 MHz, CDCl3): d = 161.2 (C=O),
155.4 (C–O), 152.8 (C–O), 147.2 (C–O), 143.6, 142.1,
142.0, 132.9, 132.7, 132.6, 130.0, 129.7, 129.5, 129.4,
124.6, 124.4, 123.9, 123.6, 123.4, 122.6, 122.2, 121.8,
119.0, 118.0, 117.1, 116.6, 114.1, 113.3, 102.4, 41.5 (CH),
27.7 (CH2), 27.3 (CH2), 22.1 (CH2) ppm; IR (KBr):
ꢀ
(CH2), 22.3 (CH2) ppm; IR (KBr): m = 3,043 (CH arom),
2,946 (CH aliph), 2,894 (CH aliph), 2,829, 1710 (C=O),
1,664, 1,626 (C=C), 1,487 (C=C), 1,454 (C=C), 1,388,
1,119, 762 (C–Cl) cm-1
ꢀ
.
m = 3,075 (CH arom), 2,920 (CH aliph), 2,833 (CH aliph),
1,711 (C=O), 1,624 (C=C), 1,512, 1,339 (NO2) cm-1
.
8,9,10,11-Tetrahydro-11-(4-methylbenzylidene)-7-(4-meth-
ylphenyl)-6H,7H-chromeno[4,3-b]chromen-6-one
11-(4-Bromobenzylidene)-7-(4-bromophenyl)-8,9,10,11-
tetrahydro-6H,7H-chromeno[4,3-b]chromen-6-one
(3g, C29H20Br2O3)
(3d, C31H26O3)
Yield 85 %; m.p.: 218–219 °C; 1H NMR (400 MHz,
CDCl3): d = 8.02 (dd, J = 8.0 Hz, 1.2 Hz, 1H, ArH),
7.57 (m, 1H, ArH), 7.13–7.41 (m, 12H, ArH, CH =), 4.42
(s, 1H, CH–Ar), 2.83 (m, 1H, CH of CH2), 2.69 (m, 1H,
CH of CH2), 2.42 (s, 3H, CH3), 2.34 (s, 3H, CH3), 2.19 (m,
2H, CH2), 1.73 (m, 2H, CH2) ppm; 13C NMR (100 MHz,
CDCl3): d = 161.6 (C=O), 155.0, 152.7, 141.9, 139.5,
136.8, 136.7, 134.2, 131.7, 129.5, 129.3, 129.2, 128.9,
128.4, 124.0, 122.7, 122.6, 117.1, 116.7, 114.8, 103.8, 41.0
(CH), 27.7 (CH2), 27.2 (CH2), 22.4 (CH2), 21.2 (CH3),
Yield 85 %; m.p.: 295-297 °C; 1H NMR (400 MHz,
CDCl3): d = 8.00 (dd, J = 8.0 Hz, 1.2 Hz, 1H, ArH),
7.27–7.62 (m, 12H, ArH, CH=), 4.42 (s, 1H, CH–Ar), 2.78
(m, 1H, CH of CH2), 2.65 (m, 1H, CH of CH2), 2.15 (m,
2H, CH2), 1.72 (m, 2H, CH2) ppm; 13C NMR (100 MHz,
CDCl3): d = 161.4 (C=O), 155.1 (C–O), 152.7 (C–O),
141.9 (C–O), 141.3, 135.8, 132.1, 131.7, 131.4, 130.9,
130.6, 130.3, 124.2, 122.6, 122.0, 121.2, 120.9, 117.2,
116.9, 114.5, 103.1, 41.0 (CH), 27.6 (CH2), 27.1 (CH2),
ꢀ
ꢀ
21.1 (CH3) ppm; IR (KBr): m = 3,088 (CH arom), 2,927
22.3 (CH2) ppm; IR (KBr): m ¼ 3; 049 (CH arom), 2,948
(CH aliph), 2,865 (CH aliph), 1,702 (C=O), 1,662 (C=C),
1,620 (C=C), 1,490 (C=C), 1,390, 1,242, 1,200, 1,119,
1,040, 820, 746 cm-1; MS (70 eV): m/z = 446 [M?].
(CHaliph), 2,893(CHaliph), 2,829,1,708(C=O),1,665,1624
(C=C), 1,484 (C=C), 1,388, 1,244, 1,201, 1,120, 1,070, 888,
824, 762, 521 cm-1; MS (70 eV): m/z = 576 [M?].
8,9,10,11-Tetrahydro-11-(3-nitrobenzylidene)-7-(3-nitro-
phenyl)-6H,7H-chromeno[4,3-b]chromen-6-one
4-[11-(4-Cyanobenzylidene)-8,9,10,11-tetrahydro-6-oxo-
6H,7H-chromeno[4,3-b]chromen-7-yl]benzonitrile
(3h, C31H20N2O3)
(3e, C29H20N2O7)
Yield 85 %; m.p.: 267–268 °C; 1H NMR (400 MHz,
CDCl3): d = 8.29 (s, 1H, ArH), 8.23 (s, 1H, ArH), 8.17
(m, 2H, ArH), 8.05 (dd, J = 8.0 Hz, 1.2 Hz, 1H), 7.37–
7.84 (m, 8H, ArH, CH=), 4.62 (s, 1H, CH–Ar), 2.84 (m,
1H, CH of CH2), 2.71 (m, 1H, CH of CH2), 2.25 (m, 1H,
CH of CH2), 2.12 (m, 1H, CH of CH2), 1.78 (m, 2H, CH2)
ppm; 13C NMR (100 MHz, CDCl3): d = 161.3 (C=O),
155.5 (C–O), 152.8 (C–O), 148.6 (C–O), 148.2, 144.3,
142.1, 138.5, 135.2, 135.1, 132.5, 132.1, 129.6, 129.5,
129.2, 124.4, 124.0, 123.2, 122.8, 122.6, 121.8, 121.5,
117.4, 117.0, 114.2, 102.4, 41.4 (CH), 27.7 (CH2), 27.1
Yield 95 %; m.p.: 274–276 °C; 1H NMR (400 MHz,
CDCl3): d = 8.00 (dd, J = 8.0 Hz, 1.2 Hz, 1H), 7.29–
7.73 (m, 11H, ArH), 7.23 (s, 1H, CH=), 4.54 (s, 1H, CH–
Ar), 2.78 (m, 1H, CH of CH2), 2.67 (m, 1H, CH of CH2),
2.23 (m, 1H, CH of CH2), 2.10 (m, 1H, CH of CH2), 1.77
(m, 2H, CH2) ppm; 13C NMR (100 MHz, CDCl3):
d = 161.3 (C=O), 155.4 (C–O), 52.8 (C–O), 147.4
(C–O), 142.1, 141.6, 132.6, 132.5, 132.4, 132.0, 129.9,
129.4, 129.1, 128.6, 128.5, 124.4, 122.6, 122.0, 118.9,
118.7, 117.8, 117.0, 114.2, 111.3, 110.4, 102.5, 41.7 (CH),
27.7 (CH2), 27.2 (CH2), 22.1 (CH2) ppm; IR (KBr):
ꢀ
ꢀ
(CH2), 22.1 (CH2) ppm; IR (KBr): m = 3,092 (CH arom),
m = 3,047 (CH arom), 2,936 (CH aliph), 2,832 (CH aliph),
2,225 (CN), 1,707 (C=O), 1,666, 1,625 (C=C), 1,605 (C=C),
2,932 (CH aliph), 2,888 (CH aliph), 1,710 (C=O), 1,664,
1,623 (C=C), 1,522 (C=C), 1,451 (C=C), 1,394 (NO2),
1,349 cm-1; MS (70 eV): m/z = 508 [M?].
1,493 (C=C), 1,391, 1,202, 1,120, 892, 765, 554 cm-1
.
8,9,10,11-Tetrahydro-7-(naphthalen-2-yl)-11-(naphthalen-
2-ylmethylene)-6H,7H-chromeno[4,3-b]chromen-6-one
(3i, C37H26O3)
Yield 80 %; m.p.: 239-242 °C; 1H NMR (400 MHz,
CDCl3): d = 8.11 (d, J = 8.0 Hz, 1H, ArH), 7.82–7.90
(m, 7H, ArH), 7.35–7.62 (m, 11H, ArH, CH=), 4.65 (s, 1H,
CH–Ar), 2.93 (m, 1H, CH of CH2), 2.80 (m, 1H, CH of
CH2), 2.23 (m, 2H, CH2), 1.74 (m, 2H, CH2) ppm; 13C
8,9,10,11-Tetrahydro-11-(4-nitrobenzylidene)-7-(4-nitro-
phenyl)-6H,7H-chromeno[4,3-b]chromen-6-one
(3f, C29H20N2O7)
Yield 90 %; m.p.: 288–290 °C; 1H NMR (400 MHz,
CDCl3): d = 8.31 (s, 1H, ArH), 8.28 (s, 1H, ArH), 8.21
(m, 2H, ArH), 8.02 (dd, J = 7.6 Hz, 1.2 Hz, 1H), 7.38–
7.66 (m, 8H, ArH, CH =), 4.62 (s, 1H, CH–Ar), 2.83 (m,
123

Cyclization of a,a0-bis(substituted-benzylidene)cyclohexanones and 4-hydroxycoumarin
419
14. Garazd MM, Garazd YL, Khilya VP (2003) Khim Prir Soedin
39:47
NMR (100 MHz, CDCl3): d = 161.6 (C=O), 155.3 (C–O),
152.8 (C–O), 142.0 (C–O), 139.8, 134.6, 133.4, 133.3,
132.7, 132.2, 131.9, 130.5, 128.4, 128.2, 128.0, 127.9,
127.8, 127.7, 127.6, 127.5, 126.4, 126.3, 126.1, 126.0,
125.8, 124.1, 123.0, 122.8, 117.5, 116.8, 114.7, 103.5, 41.7
(CH), 27.8 (CH2), 27.4 (CH2), 22.4 (CH2) ppm; IR (KBr):
ꢀm = 3,056 (CH arom), 2,951 (CH aliph), 2,920 (CH aliph),
2,854, 1,712 (C=O), 1,664, 1,622 (C=C), 1,490 (C=C),
15. Patil AD, Freyer AJ, Eggleston DS, Haltiwanger RC, Bean MF,
Taylor PB, Caranfa MJ, Breen AL, Bartus HR, Johnson RK,
Hertzberg RP, Westley JW (1993) J Med Chem 36:4131
16. Argotte-Ramos R, Ramırez-Avila G, Rodrıguez-Gutierrez MC,
Ovilla-Munoz M, Lanz-Mendoza H, Rodrıguez MH, Gonzalez-
Cortazar M, Alvarez L (2006) J Nat Prod 69:1442
17. Verotta L, Lovaglio E, Vidari G, Finzi PV, Neri MG, Raimondi
A, Parapini S, Taramelli D, Riva A, Bombardelli E (2004) Phy-
tochemistry 65:2867
1,392, 1,197, 855, 753, 478 cm-1
.
18. Guilet D, Helesbeux J-J, Seraphin D, Sevenet T, Richomme P,
Bruneton J (2001) J Nat Prod 64:563
19. Robinson TP, Ehlers T, Hubbard RB, Bai X, Arbiser JL, Gold-
smith DJ, Bowena JP (2003) Bioorg Med Chem Lett 13:115
20. Robinson TP, Hubbard RB, Ehlers TJ, Arbiser JL, Goldsmith DJ,
Bowen JP (2005) Bioorg Med Chem 13:4007
Acknowledgments We gratefully acknowledge financial support
from the Marvdasht Branch, Islamic Azad University.
References
21. Dinkova-Kostova AT, Abeygunawardana C, Talalay P (1998) J
Med Chem 41:5287
22. Dimmock JR, Padmanilayam MP, Zello GA, Nienaber KH, Allen
TM, Santos CL, De Clercq E, Balzarini J, Manavathu EK, Stables
JP (2003) Eur J Med Chem 38:169
23. Modzelewska A, Pettit C, Achanta G, Davidson NE, Huang P,
Khan SR (2006) Bioorg Med Chem 14:3491
24. Piantadosi C, Hall IH, Irvine JL, Carlson GL (1973) J Med Chem
16:770
25. Rostamizadeh S, Amani MA, Mahdavinia GH, Amiri G, Sepeh-
rian H (2010) Ultrason Sonochem 17:306
1. Bonsignore L, Loy G, Secci D, Calignano A (1993) Eur J Med
Chem 28:517 (and references cited therein)
2. Kumar S, Hernandez D, Hoa B, Lee Y, Yang JS, McCurdy A
(2008) Org Lett 10:3761
3. Rawat M, Prutyanov V, Wulff WD (2006) J Am Chem Soc
128:11044
4. Fedorova OA, Maure F, Chebunkova AV, Strokach YP, Valova
TM, Kuzmina LG, Howard JAK, Wenzel M, Gloe K, Lokshin V,
Samat A (2007) J Phys Org Chem 20:469
26. Rostamizadeh S, Amani MA, Mahdavinia GH, Sepehrian H,
Ebrahimi S (2010) Synthesis 1356
27. Khoshkholgh MJ, Lotfi M, Balalaie S, Rominger F (2009)
Tetrahedron 65:4228
28. Chen Z, Zhu Q, Su W (2011) Tetrahedron Lett 52:2601
29. Lin X, Dai X, Mao Z, Wang Y (2009) Tetrahedron 65:9233
30. Dong Z, Feng J, Cao W, Liu X, Lin L, Feng X (2011) Tetrahe-
dron Lett 52:3433
5. Hepworth JD, Heron BM (2005) Prog Heterocycl Chem 17:33
6. Delbaer S, Micheau J-C, Vermeersch G (2003) J Org Chem
68:8968
7. Tang Y, Oppenheimer J, Song Z, You L, Zhang X, Hsung RP
(2006) Tetrahedron 62:10785
8. McKee TC, Fuller RW, Covington CD, Cardellina JH II, Gula-
kowski RJ, Krepps BL, McMahon JB, Boyd MR (1996) J Nat
Prod 59:754
31. Mei RQ, Xu XY, Li YC, Fu JY, Huang QC, Wang LX (2011)
Tetrahedron Lett 52:1566
32. Liu Y, Zhu J, Qian J, Jiang B, Xu Z (2011) J Org Chem 76:9096
33. Dong Z, Wang L, Chen X, Liu X, Lin L, Feng X (2009) Eur J Org
Chem 5192
34. Khoshkholgh MJ, Lotfi M, Balalaie S, Rominger F (2009) Tet-
rahedron 65:4228
35. Mahdavinia GH, Mirzazadeh M (2012) E-J Chem 9:49
9. McKee TC, Covington CD, Fuller RW, Bokesch HR, Young S,
Cardellina JH II, Kadushin MR, Soejarto DD, Stevens PF, Cragg
GM, Boyd MR (1998) J Nat Prod 61:1252
10. Wu S-J, Chen I-S (1993) Phytochemistry 34:1659
11. Jung EJ, Park BH, Lee YR (2010) Green Chem 12:2003
12. Murray RDH, Mendez J, Brown RA (1982) The Natural Cou-
marins. Wiley, New York
13. Fylaktakidou KC, Hadjipavlou-Litina DJ, Litinas KE, Nicolaides
DN (2004) Curr Pharm Des 10:3813
123