Synthesis and biological activity of 4-hydroxy-3-(1,5-diaryl-3-oxo-pent-4-enyl)chromen-2-ones

Article abstract of DOI:10.1002/cjoc.201090111

The substituted warfarin acid chalcones have been prepared by condensation of warfarin acid and aromatic/aliphatic aldehyde using aq. NaOH as catalyst. The method is simple, cost-effective and gives good yield in a short reaction time. All the compounds synthesized have been characterized by IR, NMR and Mass spectra. A new series of 4-hydroxy-3-(3-oxo-1,5-diaryl-3-oxo-pent-4-enyl)-chromen-2-ones were synthesized and submitted to biological activity. Result of the biological screening showed the compounds 3b, 3h being the most effective among the various treatments in antimicrobial screening. Compounds 3c, 3d, 3k and 3l showed moderate activity against the microorganisms tested. Compounds 3e, 3h have shown good antifungal activity.

Full text of DOI:10.1002/cjoc.201090111

FULL PAPER
Synthesis and Biological Activity of 4-Hydroxy-3-(1,5-diaryl-3-
oxo-pent-4-enyl)chromen-2-ones
Jadhav, Mohan R.
Shinde, Devanand B.*
Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University,
Aurangabad 431004, India
The substituted warfarin acid chalcones have been prepared by condensation of warfarin acid and aro-
matic/aliphatic aldehyde using aq. NaOH as catalyst. The method is simple, cost-effective and gives good yield in a
short reaction time. All the compounds synthesized have been characterized by IR, NMR and Mass spectra. A new
series of 4-hydroxy-3-(3-oxo-1,5-diaryl-3-oxo-pent-4-enyl)-chromen-2-ones were synthesized and submitted to
biological activity. Result of the biological screening showed the compounds 3b, 3h being the most effective among
the various treatments in antimicrobial screening. Compounds 3c, 3d, 3k and 3l showed moderate activity against
the microorganisms tested. Compounds 3e, 3h have shown good antifungal activity.
Keywords chalcone, antibacterial, warfarin acid
Introduction
protein,17 sackuranetin,18,19 homoeriodictyl, eriodic-
tyol,20 cynomacturin,21 etc. Chalcone derivatives are
associated with some important biological activity such
as antitubercular, anthelmentic,22 funngicidal,23 antioxi-
dant,23-26 antimalerial,27 anti-inflammatory28 and anti-
tumor agent.29
Warfarin acid occupies an important place in organic
chemistry. Warfarin acid was synthesized by condensa-
tion of 4-hydroxycoumarin with benzylacetone,30-33
which possesses biological activity like anticonvulsant,34
inflammation,35 antagonists36 and heart diseases.37
Heterocycles are abundant in nature and are of great
significance to life because of their structural subunits
existing in many natural products such as vitamins,
harmones, antibiotics etc.1 Hence they have attracted
attention in the design of biologically active molecules.2
A practical method for the synthesis of such compounds
is of great interest in the synthetic organic chemistry.
Among the heterocycles, 1,3-thiazines are a class of
compounds with biological activity, such as antimicro-
bial,3 antitumor,4 antioxidant,5 calcium channel modu-
lator,6 and antipyretic.7
On the other hand, the classes of pyrimidines possess
abroad spectrum of biological effectiveness such as anti-
tubercular,8 antitumor,9 anticancer,10 and prostaglandin
bindings11 and antibacterial properties.12-15
In view of these properties and increasing importance
in pharmaceutical and biological field, it was interesting
and chalenging to synthesize some new chemical entities
involving an active pharmacophore, combination with
condensing compound in a single molecular frame work
to evaluate their biological activities.
The Claisen-Schmidt condensation reaction is an im-
portant reaction for ketoethylenic group formation.
Kostanecki and Tambo assigned the name chalcone,16 the
chalcones are intermediate compounds for the synthesis of
various heterocyclic compounds such as pyrazolines,
quinoxalines, pyrimidines, pyridines, isooxazalines,
flavones, and flavanoles as well as certain compound
like deoxibenzoins and hydantoins which are of some
therapeutic value. The chalcones have been found to be
useful in proving the structure of natural products like
Present work
Here we have described synthesis, characterization
and biological activity of new series of 4-hydroxy-3-
(1,5-diaryl-3-oxo-pent-4-enyl)-chromen-2-ones as anti-
bacterial, antifungal agents, along with their in vitro
biological activity (MIC activity). The synthesis of all
new compounds (3a—3q) is outlined in Scheme 1. They
were obtained in high purity and good yield. The sub-
stituted chalcones were synthesized by Claisen-Schmidt
condensation by reacting warfarin acid and aro-
matic/aliphatic aldehyde using aq. NaOH. The method
is simple, cost-effective and good yield. Structures of all
new chalcones (3a—3q) were established on the basis
1
of IR, H NMR and Mass (ES/MS). Among the new
chalcones screened for biological activity, compounds
3b, 3h, 3e and 3h, were found to demonstrate good ac-
tivity among the various treatments in antimicrobial and
antifungal screening respectively. Compounds 3c, 3k,
3m, 3o and 3l exhibited activity against the specific mi-
croorganism tested.
*
E-mail: apimohan@gmail.com; Tel.: 0091-0240-2400431
Received February 7, 2009; revised September 24, 2009; accepted October 27, 2009.
Chin. J. Chem. 2010, 28, 555— 560
© 2010 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
555

Jadhav & Shinde
FULL PAPER
Numerous methods have been reported in the litera-
ture to synthesize chalcone from aldehyde and ketone,
using alcohol as solvent. Although the base-catalyzed
reaction of aldehyde with ketenes of the type
RCH2COCH3 can in principally, occur with two possi-
ble orientations. Condensation of aromatic/aliphatic al-
dehydes with such ketones usually occurs at the methyl
group.38 The present communication reports the con-
densation of warfarin acid and aromatic aldehyde in
30% aqueous NaOH. It was observed that condensation
occurs at methyl (CH3) group rather than (CH2) group.
The formation of chalcone was confirmed by chemical
methods and characterized by modern analytical meth-
ods. In conclusion, we have demonstrated an efficient
and simple alternative for the preparation of substituted
new chalcone via the condensation using aqueous
NaOH. All the new compounds (3a—3q) were sub-
jected to biological screening for antibacterial and anti-
fungal activity. The MIC was determined using tube
dilution method. Antifungal activity was determined
against Candida albicans, and for comparasion Flu-
conazole was used as standard. The results are presented
in Tables 2 and 3. Prominent advantages of this method
are operational simplicity, good yield, organic sol-
vent-free and economic easy workup procedure.
Experimental section
Melting points were determined on a quality precise
melting point apparatus and are uncorrected. H NMR
1
spectra were recorded on Brucker 400 MHz spectrome-
ter. Chemical shifts (δ) are reported relative to TMS as
an internal standard. Electron spray ionization mass
spectra (ES-MS) were recorded on a water micromass
Quattro spectrometer. All the solvents and reagents used
were of AR grade and were used without further purifica-
tion. IR spectra of the compounds of this series have been
scanned on JASCO spectrophotometer using KBr pellets.
General procedure for synthesizing chalcones (3a—
3q)
To a well-stirred mixture of warfarin acid (0.01 mol)
and adehyde (0.01 mol) in water, was added a solution of
30% aqueous NaOH. The reaction mixture was stirred
overnight at room temperature. Reaction completion was
checked on TLC [V(Methanol)∶V(chloroform)＝8∶2].
After the reaction was complete, the reaction mixture
was poured in cooled 10% HCl solution. The precipitate
obtained was filtered to get targeted desired chalcone.
The solid was washed with water until free from acid
and crystallized from ethanol, to afford chalcone. All
new chalcones of this series (3a—3q), were synthesized
by using the same procedure (Scheme 1).
Scheme 1
Table 1 Physical data of 3a—3q
Entry
3a
3b
3c
R
H
R1
Yield/%
Molecular formula/Mr
m.p./℃
105—110
132
C6H5
85
93
93
85
95
93
85
85
88
92
88
85
88
90
90
95
85
C26H20O4/396
H
4-NO2C6H4
4-ClC6H4
4-OCH3C6H4
3-NO2C6H4
2-ClC6H4
2-Furyl
C26H19NO6/441
C26H19ClO4/430
C27H22O5/426
H
128
3d
3e
H
147
H
C26H19NO6/441
C26H19ClO4/430
C24H18O5/386
127
3f
H
138
3g
3h
3i
H
103
4-OCH3
4-OCH3
4-OCH3
4-OCH3
4-OCH3
4-Cl
4-Cl
4-Cl
4-Cl
4-Cl
C6H5
C27H22O5/426
141
4-NO2C6H4
4-ClC6H4
4-OCH3C6H4
2-Furyl
C27H21O7/471
152
3j
C27H21ClO5/460
C28H24O6/456
148
3k
3l
161
C25H20O6/416
162
3m
3n
3o
3p
3q
C6H5
C26H19ClO4/430
C26H18Cl2O4/464
C27H21ClO5/460
C26H18NClO6/475
C24H17ClO5/420
135
4-ClC6H4
4-OCH3C6H4
3-NO2C6H4
2-Furyl
149
152
145
170
556
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© 2010 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2010, 28, 555— 560

4-Hydroxy-3-(1,5-diaryl-3-oxo-pent-4-enyl)chromen-2-ones
Spectral evaluation of all new synthesized com-
Table 2 Antibacterial activity of 3a—3q, as minimum inhibi-
pounds (3a— 3q)
tory concentration
－
1
4-Hydroxy-3-(3-oxo-1,5-diaryl-3-oxo-pent-4-enyl)-
chromen-2-one (3a) 1H NMR (DMSO-d6, 400 MHz)
δ: 3.50 (d, J＝12.7 Hz, 2H), 4.90 (t, J＝14.1 Hz, 1H),
6.58 (d, J＝14.3 Hz, 1H), 6.93 (d, J＝15.2 Hz, 1H),
7.10—7.95 (m, 14H, Ar-H), 10.00 (s, 1H－, OH); IR (KBr)
Antibacterial activity [MIC/(µg•mL )]
Compound
E. coli
25
S. aureus
50
B. subtilis
70
Warfarin acid
3a
100
25
—
—
1
3b
25
25
ν: 3500, 3027, 1684, 1610, 1568, 880 cm ; ES/MS m/z:
397 (M＋H)＋. Anal. calcd for C26H20O4: C 78.77, H
3c
25
75
50
5.09; found C 78.72, H 5.07.
3d
50
75
100
50
4-Hydroxy-3-[5-(4-nitro-phenyl)-3-oxo-1-phenyl-
pent-4-enyl]-chromen-2-one (3b) 1H NMR (DMSO-d6,
400 MHz) δ: 3.50 (d, J＝12.4 Hz, 2H), 3.72 (t, J＝13.2
Hz, 1H), 6.40 (d, J＝14.3 Hz, 1H), 6.70 (d, J＝15.3 Hz,
1H), 7.25—7.80 (m, 13H, Ar-H), 9.20 (s, 1H, OH); －IR
3e
25
25
3f
25
50
25
3g
75
100
25
—
3h
25
25
1
(KBr) ν: 3545, 3027, 1680, 1600, 1560, 1375, 880 cm ;
3i
50
25
25
ES/MS m/z: 442 (M＋H)＋. Anal. calcd for C26H19NO6:
C 70.44, H 4.34, N 3.17; found C 70.04, H 4.30, N 3.12.
4-Hydroxy-3-[5-(4-chloro-phenyl)-3-oxo-1-phenyl-
pent-4-enyl]-chromen-2-one (3c) 1H NMR (DMSO-d6,
400 MHz) δ: 3.55 (d, J＝12.2 Hz, 2H), 3.72 (t, J＝13.8
Hz, 1H), 6.40 (s, J＝14.4 Hz, 1H), 6.70 (d, J＝151 Hz,
1H), 7.20—7.80 (m, 13H, Ar-H), 9.50 (s, 1H, OH); －IR
3j
75
50
—
3k
25
25
50
3l
25
25
75
3m
25
25
50
3n
50
90
100
25
3o
3p
25
30
1
(KBr) ν: 3400, 3027, 1700, 1600, 1570, 880, 750 cm ;
70
90
—
ES/MS m/z: 431 (M＋H)＋. Anal. calcd for C26H19ClO4:
3q
52
35
50
C 72.47, H 4.44; found C 72.40, H 4.41.
Streptomycin
Neomycin
10
10
10
4-Hydroxy-3-[5-(4-methoxy-phenyl)-3-oxo-1-
phenyl-pent-4-enyl]-chromen-2-one (3d) 1H NMR
(DMSO-d6, 400 MHz) δ: 2.20 (s, 3H, OCH3), 3.50 (d,
J＝12.5 Hz, 2H), 5.00 (s, br, 1H, OH), 4.10 (t, J＝14 Hz,
1H), 6.50 (d, J＝14.5 Hz, 1H), 6.82 (d, J＝15.3 Hz, 1H),
7.10—7.79 (m, 9H, Ar-H), 7.40—7.60 (d, 4H, Ar-H);－IR
30
30
30
Table 3 Antifungal activity of 3a—3q in spore germination
inhibition (%) at different concentration against Candida albicans
－
1
Concentration/(µg•mL )
1
(KBr) ν: 3400, 3027, 170＋0, 1600, 1570, 880, 750 cm ;
Compound
160
55
320
67
480
69
640
72
ES/MS m/z: 427 (M＋H) . Anal. calcd for C27H22O5: C
76.04, H 5.20; found C 74.0, H 5.10.
Warfarin acid
4-Hydroxy-3-[5-(3-nitro-phenyl)-3-oxo-1-phenyl-
pent-4-enyl]-chromen-2-one (3e) 1H NMR (DMSO-d6,
400 MHz) δ: 3.35 (d, J＝12.1 Hz, 2H), 4.20 (t, J＝13.7
Hz, 1H), 6.60 (d, J＝14.7 Hz, 1H), 6.80 (d, J＝15.4 Hz,
1H), 7.10—7.79 (m, 9H, Ar-H), 7.40—7.60 (d, J＝14.2
Hz, 4H, Ar-H), 9.00 (s, 1H, OH); IR －(KBr) ν: 3450,
3a
23.4
45.4
42.0
19.6
79.0
77.1
68.2
82.4
71.3
59.7
77.3
75.1
50.4
61.4
45.3
77.9
75.3
84.0
26.2
79.1
49.4
27.0
84.0
79.3
74.1
86.4
78.2
65.2
78.0
78.7
48.9
60.3
72.6
89.3
66.7
87.0
28.0
89.5
83.1
29.0
87.0
81.0
82.1
87.6
79.4
69.9
81.0
80.3
51.2
59.8
80.1
86.9
78.9
95.0
29.0
91.0
90.0
31.2
88.4
86.5
86.4
92.3
87.6
72.1
84.0
83.2
42
3b
3c
3d
3ea
1
3100, 1670, ＋1620, 1570, 880, 1375 cm ; ES/MS m/z:
3f
442 (M＋H) . Anal. calcd for C26H19NO4: C 70.74, H
4.34, N 3.17; found C 70.42, H 4.52, N 3.18.
3g
3ha
4-Hydroxy-3-[5-(2-chloro-phenyl)-3-oxo-1-phenyl-
pent-4-enyl]-chromen-2-one (3f) 1H NMR (DMSO-d6,
400 MHz) δ: 3.45 (d, J＝12.3 Hz, 2H), 3.60 (t, J＝13.8
Hz, 1H), 6.72 (d, J＝14.2 Hz, 1H), 6.80 (d, J＝15.3 Hz,
1H), 7.10—7.25 (m, 13H, Ar-H), 8.90 (s, 1H, OH); －IR
3i
3j
3k
3l
1
(KBr) ν: 3450, 3100, 1750, 1620, 1570, 880, 750 cm ;
3m
ES/MS m/z: 431 (M＋H)＋. Anal. calcd for C26H19ClO4:
3n
58.7
79.5
88
C 72.47, H 4.44; found C 72.43, H 4.41.
3o
3p
4-Hydroxy-3-(5-furan-2-yl-3-oxo-1-phenyl-pent-4-
enyl)-chromen-2-one (3g) 1H NMR (DMSO-d6, 400
MHz) δ: 3.45 (d, J＝12.2 Hz, 2H), 3.52 (t, J＝13.4 Hz,
1H), 6.75 (d, J＝14.2 Hz, 1H), 6.83 (d, J＝15.3 Hz, 1H),
6.60 (dd, J＝14.3, 13.8 Hz, 1H, Ar-H), 6.95 (dd, J＝
14.3 Hz, 1H, Ar-H), 7.10—7.25 (m, 9H, Ar-H), 7.60 (d,
3q
90
Fluconazole
98.0
a Compound shows high activity; rest all shows moderate activity.
Chin. J. Chem. 2010, 28, 555— 560
© 2010 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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FULL PAPER
J＝13.8 Hz, 1H, Ar-H), 11.50 (s, 1H, O－H); IR (KBr) ν:
C26H19ClO4: C 72.47, H 4.44; found C 72.40, H 4.42.
4-Hydroxy-3-[1,5-bis-(4-chloro-phenyl)-3-oxo-
pent-4-enyl]-chromen-2-one (3n) 1H NMR (DMSO-
d6, 400 MHz) δ: 3.40 (d, J＝12.2 Hz, 2H), 3.72 (t, J＝
13.2 Hz, 1H), 6.40 (d, J＝14.2 Hz, 1H), 6.70 (d, J＝
15.2 Hz, 1H), 7.20—7.80 (m, 12H, Ar-H), 9.50 (s, 1H,
OH); IR (KBr) ν: 34750, 3027, 1700, 1600, 1570, 880,
1
3450, 3100, ＋1750, 1620, 1570, 880 cm ; ES/MS m/z:
387 (M＋H) . Anal. calcd for C24H18O5: C 74.60, H 4.7;
found C 74.52, H 4.60.
4-Hydroxy-3-[1-(4-methoxy-phenyl)-3-oxo-5-
phenyl-pent-4-enyl]-chromen-2-one (3h) 1H NMR
(DMSO-d6, 400 MHz) δ: 2.30 (s, 3H, OCH3), 3.50 (d,
J＝11.9 Hz, 2H), 3.60 (t, J＝13.5 Hz, 1H), 6.72 (d, J＝
14,4 Hz, 1H), 6.80 (d, J＝15.4 Hz, 1H), 7.10—7.25 (m,
13H, Ar-H), 8.70 (s, 1H, OH); IR (KBr) ν: 3450, 310＋0,
＋
－1
750 cm ; ES/MS m/z: 465 (M＋H) . Anal. calcd for
C26H19ClO4: C 72.47, H 4.44; found C 72.43, H 4.41.
4-Hydrpxy-3-[1-(4-chloro-phenyl)-5-(4-methoxy-
phenyl)-3-oxo-pent-4-enyl]-chromen-2-one (3o) 1H
NMR (DMSO-d6, 400 MHz) δ: 1.80 (s, 3H, CH3), 3.25
(d, J＝11.9 Hz, 2H), 3.60 (t, J＝13.1 Hz, 1H), 6.40 (d,
－1
1750, 1620, 1570, 880 cm ; ES/MS m/z: 427 (M＋H) .
Anal. calcd for C27H22O5: C 76.04, H 5.20; found C
76.00, H 5.12.
4-Hydroxy-3-[1-(4-methoxy-phenyl)-5-(4-nitro-
phenyl)-3-oxo-pent-4-enyl]-chromen-2-one (3i) 1H
NMR (DMSO-d6, 400 MHz) δ: 2.30 (s, 3H, OCH3),
3.50 (d, J＝12.2 Hz, 2H), 3.70 (t, J＝13.7 Hz, 1H), 6.20
(d, J＝14.3 Hz, 1H), 6.50 (d, J＝15.4 Hz, 1H), 7.10—
7.25 (m, 12H, Ar-H), 9.70 (s, 1H, OH); IR (KBr) ν:
J＝14.4 Hz, 1H), 6.70 (d, J＝15.4 Hz, 1H), 7.20—7.4
(m, 12H, Ar-H), 8.70 (s, 1H, OH); IR－(KBr) ν: 3400,
1
3200, 1700, ＋1620, 1570, 880, 750 cm ; ES/MS m/z:
461 (M＋H) . Anal. calcd for C27H21ClO5: C 70.36, H
4.59; found C 70.34, H 4.55.
4-Hydroxy-3-[1-(4-chloro-phenyl)-5-(3-nitro-
phenyl)-3-oxo-pent-4-enyl]-chromen-2-one (3p) 1H
NMR (DMSO-d6, 400 MHz) δ: 3.25 (d, J＝12.4 Hz,
2H), 3.60 (t, J＝13.1 Hz, 1H), 6.72 (d, J＝14.2 Hz, 1H),
－1
3450, 3100, 1670＋, 1620, 1570, 880, 1375 cm ; ES/MS
m/z: 472 (M＋H) . Anal. calcd for C27H21NO7: C 69.78,
H 4.49, N 2.97; found C 68.72, H 4.45, N 2.95.
4-Hydroxy-3-[5-(4-chloro-phenyl)-1-(4-methoxy-
phenyl)-3-oxo-pent-4-enyl]-chromen-2-one (3j) 1H
NMR (DMSO-d6, 400 MHz) δ: 2.75 (s, 3H, OCH3),
3.45 (d, J＝12.1 Hz, 2H), 3.63 (t, J＝14.1 Hz, 1H), 6.78
(d, J＝14.5 Hz, 1H), 6.83 (d, J＝15.4 Hz, 1H), 7.10—
7.25 (m, 12H, Ar-H), 9.10 (s, 1H, OH); IR (KBr) ν:
6.80 (d, J＝15.3 Hz, 1H), 7.10—7.25 (m, 12H, Ar-H),
8.70 (s, 1H, OH); IR (KBr) ν: 3400, 3000, 1690, 162＋0,
－1
1570, 1370, 890, 750 cm ; ES/MS m/z: 476 (M＋H) .
Anal. calcd for C26H18NClO6: C 65.62, H 3.81, N 2.94;
found C 65.60, H 3.79, N 3.01.
4-Hydroxy-[1-(4-chloro-phenyl)-5-furan-2-yl-3-
－1
3400, 3200, 1700, 1620, 1570, 890, 750 cm ; ES/MS
oxo-pent-4-enyl]-chromen-2-one (3q)
1H NMR
m/z: 461 (M＋H)＋. Anal. calcd for C27H21ClO5: C 70.36,
(DMSO-d6, 400 MHz) δ: 3.25 (d, J＝12.4 Hz, 2H), 3.52
(t, J＝13.2 Hz, 1H), 6.40 (d, J＝14.2 Hz, 1H), 6.83 (d,
J＝15.4 Hz, 1H), 6.60 (dd, J＝13.7, 14.2 Hz, 1H, Ar-H),
6.95 (dd, J＝13.7, 14.2 Hz, 1H, Ar-H), 7.30 (s, 1H,
Ar-H), 7.50—8.10 (m, 8H, Ar-H), 8.90 (s, 1H, OH); －IR
H 4.59; found C 70.25, H 4.5.
4-Hydroxy-3-[1,5-bis-(4-methoxy-phenyl)-3-oxo-
pent-4-enyl]-chromen-2-one (3k) 1H NMR (DMSO-d6,
400 MHz) δ: 1.80 (s, 3H, CH3), 2.20 (s, 3H, CH3), 3.20 (d,
J＝12.1 Hz, 2H), 3.50 (t, J＝12.7 Hz, 1H), 6.20 (d, J＝
14.2 Hz, 1H), 6.85 (d, J＝15.2 Hz, 1H), 7.20—7.4 (m,
12H, Ar-H), 8.70 (s, 1H, OH); IR (KBr) ν: 3400, 320＋0,
1
(KBr) ν: 3350, 3000, 169＋0, 1620, 1570, 890, 750 cm ;
ES/MS m/z: 421 (M＋H) . Anal. calcd for C24H17ClO5:
C 68.50, H 4.07; found C 68.92, H 4.11.
－1
1700, 1620, 1570, 890 cm ; ES/MS m/z: 457 (M＋H) .
Anal. calcd for C28H24O6: C 73.67, H 5.30; found C
73.65, H 5.25.
Results and discussion
Antimicrobial activity
4-Hydroxy-3-[5-furan-2-yl-1-(4-methoxy-phenyl)-
3-oxo-pent-4-enyl]-chromen-2-one (3l)
1H NMR
The compounds 3a—3q were screened for their an-
tibacterial human pathogenic bacteria Escheriichia coli,
Staphylococcus aurenus, and Bacillus subtilis. The
minimum inhibition concentration (MIC) was deter-
mined using the tube dilution method.39 DMF was used
as a blank and streptomycin/neomycin was used as an-
tibacterial standard. The antibacterial activity was com-
pared with the known antibiotic streptomycin/neomycin
and the results are presented in Table 2. A close assess-
ment of the data reveals that all the compounds exihi－bit
(DMSO-d6, 400 MHz) δ: 2.20 (s, 3H, OCH3), 2.50 (t,
J＝11.4 Hz, 1H), 3.42 (d, J＝13.1 Hz, 2H, CH2), 6.40 (d,
J＝14.2 Hz, 1H), 6.83 (d, J＝15.3 Hz, 1H), 6.55 (dd,
J＝13.7, 14.2 Hz, 1H, Ar-H), 6.90 (dd, J＝13.8, 13.6 Hz,
1H, Ar-H), 7.10—7.25 (m, 8H, Ar-H), 7.60 (d, J＝13.8
Hz, 1H, Ar-H), 10.25 (s, 1H, OH); IR (KBr) ν: 3400,
－1
3200,＋1690, 1620, 1570, 890 cm ; ES/MS m/z: 417 (M
＋H) . Anal. calcd for C25H20O6: C 72.11, H 4.84;
found C 72.10, H 4.81.
1
4-Hydroxy-3-[1-(4-chloro-phenyl)-3-oxo-5-phenyl-
pent-4-enyl]-chromen-2-one (3m) 1H NMR (DMSO-
d6, 400 MHz) δ: 3.20 (d, J＝12.1 Hz, 2H), 3.72 (t, J＝
13.1 Hz, 1H), 6.40 (d, J＝14.1 Hz, 1H), 6.70 (d, J＝
15.3 Hz, 1H), 7.20—7.80 (m, 13H, Ar-H), 9.50 (s, 1H,
OH); IR (KBr) ν: 3400, 3027, 1700,＋1600, 1570, 880,
antibacterial activity ranging from 25 to 100 µg•mL .
The compounds 3b and 3h were highly active against all
the three organisms. Both compounds have oxygen
containing electronegative group on benzene nucleus.
Compounds 3e, 3k and 3l were active against E. coli
and S. aureus. Here too oxygen containing electronega-
tive group is present on benzene nucleus (both from
－1
750 cm ; ES/MS m/z: 431 (M＋H) . Anal. calcd for
558
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© 2010 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2010, 28, 555— 560

4-Hydroxy-3-(1,5-diaryl-3-oxo-pent-4-enyl)chromen-2-ones
warfarin moiety and aldehyde moiety). Compound 3f is
highly active against E. coli and B. subtilis. Here chlo-
rine as an electronegative group is present on benzene
nucleus (R1). Compound 3i is highly active against S.
aureus and B. subtilis. Compound 3a is almost inactive
against all three organisms employed. Compound 3m is
active against E. coli and S. aureus. Compound 3o is
active against E. coli and B. sublitis. Compounds 3n, 3p
and 3q are inactive against all three organisms employed.
From the screened results it can be concluded that the
functional group like methoxy or nitro as a substituent on
benzene nucleus has shown promising activity. Com-
pounds 3m and 3o having chlorine as electronegative
group have shown activity against E. coli and S. aureus.
Compound 3m has chlorine group and 3o has electro-
negative chlorine and methoxy group on respective
benzene nucleus. Compound 3n has electronegative
chloro group on both benzene nucleus, which may have
contributed towards inactivity. 3p and 3q have
electronegative group chloro and methoxy. Both
compounds are found to be inactive for human pathogen
bacteria. This can be contributed to neutralizing effect of
one electronegative by other. As a general conclusion
apart from the nature of the group it is the specific group
having oxygen item and position on benzene nucleus
that is effective for promising contribution to antimicro-
bial activity.
sui, K.; Shimoda, T.; Horie, M.; Osakada, M. J. Am. Chem.
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3
4
5
6
Antifungal activity
The chalcones (3a—3q) were also screened for their
antifungal activity against Candida albicans at 160, 320,
－1
480 and 640 µg•mL concentration, using agar plate
technique.40 The results are presented in Table 3. The
antifungal activity was compared with the known anti-
fungal fluconazole. The examination of the data reveals
that compounds 3e and 3h are highly active against
Candida albicans. Compounds 3b, 3c and 3d are inac-
tive as all values are far away from the standard value
for Fluconazole. From the structure of 3e it will be evi-
dent that nitro group is at 3 position of R1 which could
have contributed to antifungal activity. Compounds 3k,
3l, 3p and 3q show moderate antifungal activity. Com-
pound 3i shows activity at high concentration. Com-
pounds 3m, 3n and 3o do not have promising antifungal
activity.
7
8
9
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From the date presented in Tables 2 and 3 it appears
that the compounds 3e and 3h shows antibacterial and
antifungal activity and hence can be considered for fur-
ther screening as perspective molecules having dual ac-
tivity. Both are having electron withdrawing group hav-
ing oxygen item. 3b and 3h can be independently fur-
ther tried for their application in view of their promiss-
ing antibacterial activity as future perspective molecule.
10 (a) Ahluwalia, V. K.; Kalia, N.; Bala, S. Indian J. Chem.
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11 Gschwendt, M.; Kisttstein, W.; Furstenberg, G.; Mark, F.
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Chin. J. Chem. 2010, 28, 555— 560