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Der Pharma Chemica, 2009, 1(2): 145-152
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ISSN 0975-413X

Synthesis of some new biologically active chalcones and flavones

S. S. Mokle, Y.B. Vibhute*

*Laboratory of Organic Synthesis, P.G. Department of Chemistry,

Yeshwant Mahavidyalaya, Nanded, M.S, India
___________________________________________________________________________

Abstract

New chalcones (3a-g) were synthesized from 2-chloro-6-methyl-quinoline-3-carbaldehyde

(2) and halohydroxysubstitued acetophenones (1a-g) via Claisen-Schmidt condensation.
Further new flavones (4a-g) were synthesized by oxidative cyclisation of chalcones (3a-g)
using microwave as well as by conventional method. The structures of synthetic compounds
have been characterized by analytical and spectral data. All the synthesized compounds have
been evaluated for their antibacterial activity and studied the effect on seed germination of
wheat (Triticum aestivum).

Keywords: 2-chloro-6-methyl-quinoline-3-carbaldehyde, halohydroxysubstituted acetophen

-ones, chalcones, flavones, antibacterial activity and seed germination.
___________________________________________________________________________

Introduction
Chalcones, or 1,3-diaryl-2-propen-1-ones, are natural/synthetic compounds belonging to the
flavonoid family.Chalcones of plant origin are known[1].Chalcones possess a broad spectrum
of biological activities, including potent antimitotic[2], antibacterial[3], antifibrogenic[4],
anticancer[5], antitrichomonal[6], anti-inflammatory[7], antileishmanial[8], cytotoxic and
anti-trypanosoma cruzi[9] activities. While the flavonoid compounds are a group of natural
products found in fruits, vegetables, nuts, seeds and flowers as well as in teas and are
important constituent of human diet. They have been demonstrated to possess
antioxdidant[10], antihypertensive[11], antiallergic[12], antinocicepative[13], trypsin
inhibitors[14], plant growth regulator[15], antibacterial and antifungal[16,17] activities.

In the last few years microwave induced organic reaction enhancement (MORE) chemistry
has gained popularity as a non-conventional technique for rapid organic synthesis[18] and
many researchers have described accelerated organic reactions, and a large number of papers
has appeared. Proving the synthetic utility of MORE chemistry in routine organic
synthesis[19,20]. It has been termed as ‘e-chemistry’ because it is easy, effective, economical

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and ecofriendly and is belived to be a step toward green chemistry. In view of these
observations and in continuation of our work on biologically active chalcones and their
heterocycles[21], we have been planned to synthesize the new flavones (4a-g) from chalcones
(3a-g) and also studied their antibacterial activity against Xanthomanas citri (Xc), Ervinia
carotovara (Ec), Escherichia coli (E. coli) and Bacillus subtilis (Bs) using Ampicillin as a
standard drug.

Results and Discussion

Chalcones (3a-g) and flavones (4a-g) were synthesized. The structures of newly synthesized
compounds have been confirmed on the basis of elemental analysis and spectral data. From
antibacterial screening, it was found that compound 3e, 3f, 3g, 4b, 4e, 4f and 4g exhibited
good antibacterial activity against all bacteria at a concentration of 100µg/ml.

Chalcones and flavones have been tested their effect on seed germination of Wheat. All
chalcones and flavones showed maximum seed germination than control (distil water) and no
any growth of fungi was observed on seeds. The present study reveals that chalcones and
flavones which contain iodine, chlorine, bromine, methyl and hydroxy substituents showed
good antibacterial than the standard drug Ampicillin. Chalcones and flavones were acting as a
growth promoting agents for seed germination of wheat.

Materials and Methods

All melting points are taken in open glass capillaries and were found uncorrected. The purity
of compounds has been checked by TLC on silica gel G. The IR spectra in KBr were
recorded on Shimadzu spectrophotometer and 1HNMR spectra were recorded in DMSO on
Varian Inova 300 FT MHz spectrophotometer using TMS as internal standard (δ ppm).
Elemental analyses were performed on a Perkin-Elmer 240 CHN elemental analyzer.

Experimental: Synthesis of Chalcones (3a-g):

Equimolar quantities of halo substituted 2-hydroxyacetophenone (0.01mol) and 2-chloro-6-
methyl- quinoline-3-carbaldehyde (0.01 mol) were dissolved in ethanol (15 ml), under
stirring and aqueous KOH (50%, 10 ml) was added dropwise. The reaction mixture was
stirred at room temperature and kept for 14-16 hr.The reaction mixture was diluted with
water and acidified with 10% HCl.The separated solid was filtered and cryststallised from
acetic acid to give compounds (3a-g).

1-(2’-hydroxy-3’,5’-diiodophenyl)-3-(2-chloro-6-methyl-quinolin-3-yl)-2- propen-1-one (3a):

m.p. 1790C. IR (KBr) cm-1: 2999(-OH), 1638(C=O), 1569, 1495(ring C=C), 1050(C-O).
1
HNMR (300 MHz, DMSO): δ 2.40 (s, 3H, CH3), 6.93 (d, 1H, Hα), 7.37 (d, 1H, Hβ), 7.38-
δ8.49 (m, 6H, Ar-H), 12.94 (s, 1H, Ar-OH). Anal. Calcd. for C19H12O2NI2Cl (575.5):
C,39.61; H,2.08; N, 2.43. Found: C, 39.70; H, 2.05, N,2.33.

1-(2’-hydroxy-3’-iodo-5’-chlorophenyl)-3-(2-chloro-6-methyl-quinolin-3-yl)-2-propen-1-one
(3b): m.p. 1730C. IR (KBr) cm-1: 3034(-OH), 1630(C=O), 1568, 1496(ring C=C), 1052(C-
O). 1HNMR (300 MHz, DMSO): δ 2.39 (s, 3H, CH3), 6.98 (d, 1H, Hα), 7.29 (d, 1H, Hβ),
7.36- δ8.44 (m, 6H, Ar-H), 13.08 (s, 1H, Ar-OH). Anal. Calcd. for C19H12O2NICl2 (484):
C,47.10; H,2.47; N,2.89. Found: C,47.05; H,2.51; N,2.83.

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SCHME : R

R1 OH OHC CH3

+
R2 Cl N

O
1a-g 2

EtOH / KOH

R
CH3
R1 OH

N
R2 Cl

O
3a-g

Method A Method B
DMSO-I2 DMSO-I2
MW, 3-5min.

R
CH3
R1 O

N
R2 Cl

O
4a-g
where,

1a, 3a ,4a: R= I, R1= H, R2 = I 1e, 3e, 4e: R= I, R1= OH, R2= I

1b, 3b, 4b: R= I, R1= H, R2= Cl 1f, 3f, 4f: R= Cl, R1= OH, R2= Cl
1c, 3c, 4c: R= I, R1= H, R2 = CH3 1g, 3g, 4g: R= Br, R1= OH, R2= Br
1d, 3d, 4d: R= Br, R1= H, R2= Cl

1-(2’-hydroxy-3’-iodo-5’-methylphenyl)-3-(2-chloro-6-methyl-quinolin-3-yl)-2-propen-1-one
(3c): m.p.1490C. IR (KBr) cm-1: 3067(-OH), 1632(C=O), 1571, 1489(ring C=C), 1045(C-O).
1
HNMR (300 MHz, DMSO): δ δ2.41 (s, 6H, CH3), 6.92 (d, 1H, Hα), 7.33 (d, 1H, Hβ), 7.34-
δ8.42 (m, 6H, Ar-H), 13.21(s, 1H, Ar-OH). Anal. Calcd. for C20H15O2NICl (463.5): C,51.77;
H,3.23; N,3.02. Found: C,51.84; H,3.19; N,2.94.

1-(2’-hydroxy-3’-bromo-5’-chlorophenyl)-3-(2-chloro-6-methyl-quinolin-3-yl)-2-propen-1-
one (3d): m.p.1500C. IR (KBr) cm-1: 3080(-OH), 1637(C=O), 1574, 1492(ring C=C),
1055(C-O). 1HNMR (300 MHz, DMSO): δ 2.37 (s, 3H, CH3), 7.05 (d, 1H, Hα), 7.33 (d, 1H,

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Hβ), 7.35- δ8.21 (m, 6H, Ar-H), 12.95(s, 1H, Ar-OH). Anal. Calcd. for C19H12O2NBrCl2
(437): C,52.17; H,2.74; N,3.20. Found: C,52.22; H,2.71; N,3.12.

1-(2’4’-dihydroxy-3’,5’-diiodophenyl)-3-(2-chloro-6-methyl-quinolin-3-yl)-2-propen-1-one
(3e): m.p.1560C. IR (KBr) cm-1: 3386(-OH), 1635(C=O), 1574, 1485 (ring C=C), 1050(C-
O). 1HNMR (300 MHz, DMSO): δ 2.39 (s, 3H, CH3), 6.93 (d, 1H, Hα), 7.30 (d, 1H, Hβ),
7.40- δ8.22 (m, 5H, Ar-H), 10.85(s, 1H, 4’Ar-OH), 13.30(s, 1H, 2’Ar-OH). Anal. Calcd. for
C19H12O3NI2Cl (591.5): C,38.54; H,2.02; N,2.36.Found: C,38.65; H,1.98; N,2.39.

1-(2’4’-dihydroxy-3’,5’-dichlorophenyl)-3-(2-chloro-6-methyl-quinolin-3-yl)-2-propen-1-
one (3f): m.p.1750C. IR (KBr) cm-1: 3400(-OH), 1635(C=O), 1577, 1485 (ring C=C),
1056(C-O). 1HNMR (300 MHz, DMSO): δ 2.35 (s, 3H, CH3), 6.96 (d, 1H, Hα), 7.31 (d, 1H,
Hβ), 7.42- δ8.29 (m, 5H, Ar-H), 10.95(s, 1H, 2’Ar-OH), 13.27(s, 1H, 4’Ar-OH). Anal.
Calcd. for C19H12O3NCl3 (408.5): C,55.81; H,2.93; N,3.42. Found: C,55.88; H,3.01; N,3.38.

1-(2’4’-dihydroxy-3’,5’-dibromophenyl)-3-(2-chloro-6-methyl-quinolin-3-yl)-2-propen-1-
one (3g): m.p.1810C. IR (KBr) cm-1: 3392(-OH), 1637(C=O), 1569, 1483 (ring C=C),
1050(C-O). 1HNMR (300 MHz, DMSO): δ 2.39 (s, 3H, CH3), 6.97 (d, 1H, Hα), 7.32 (d, 1H,
Hβ), 7.40- δ8.26 (m, 5H, Ar-H), 10.89(s, 1H, 2’Ar-OH), 13.28(s, 1H, 4’Ar-OH). Anal.
Calcd. for C19H12O3NBr2Cl (497.5): C,45.82; H,2.41; N,2.81. Found: C,45.90; H,2.47;
N,2.76.

Synthesis of Flavones (4a-g):

Method A:
Chalcone (0.01 mol) was suspended in DMSO (10 ml) and a crystal of iodine was added to it.
The mixture was refluxed for 30-45 min. and diluted with water. The solid obtained was
filtered off, washed with 20% sodium thiosulfate and crystallized from ethyl alcohol to give
compounds (4a-g). It gave positive Mg/HCl test (yellow colouration).

Method B:
Chalcone (0.01 mol) was suspended in DMSO (10 ml) and a crystal of iodine was added to it.
The mixture was irradiated in microwave oven for the appropriate time (Table1) at 650 W.
After completion of reaction as followed by TLC examination, the solid product was washed
with 20% sodium thiosulfate and crystallized from ethyl alcohol to give compounds (4a-g). It
gave positive Mg/HCl test (yellow colouration).

2-(2-Chloro-6-methyl-quinolin-3-yl)-6,8-diiodo-chromen-4-one (4a):
m.p.1980C. IR (KBr) cm-1: 1645(C=O), 1570, 1495 (ring C=C). 1HNMR (300 MHz,
DMSO): δ 2.41 (s, 3H, OCH3), 7.09 (s, 1H, COCH), 7.40- δ8.22 (m, 6H, Ar-H). Anal. Calcd.
for C19H10O2NI2Cl (573.5): C,39.75; H,1.74; N, 2.44. Found: C, 39.70; H, 1.70, N,2.39.

6-Chloro-2--(2-Chloro-6-methyl-quinolin-3-yl)-8-iodo-chromen-4-one (4b):
m.p.1890C. IR (KBr) cm-1: 1645(C=O), 1571, 1493(ring C=C). 1HNMR (300 MHz, DMSO):
δ 2.39 (s, 3H, OCH3), 6.97 (s, 1H, COCH), 7.30- δ8.15 (m, 6H, Ar-H). Anal. Calcd. for
C19H10O2NICl2 (482): C,47.30; H,2.07; N,2.90. Found: C,47.23; H,2.01; N,2.86.

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2-(2-Chloro-6-methyl-quinolin-3-yl)-8-iodo-6-methyl-chromen-4-one (4c):
m.p.1780C. IR (KBr) cm-1: 1632(C=O), 1565, 1490(ring C=C). 1HNMR (300 MHz, DMSO):
δ δ2.45 (s, 6H, CH3), 7.01(s, 1H, COCH), 7.39- δ8.20 (m, 6H, Ar-H). Anal. Calcd. for
C20H12O2NICl (461.5): C,52.00; H,2.60; N,3.33. Found: C,51.94; H,2.69; N,3.39.

8-Bromo-6-chloro-2-(2-Chloro-6-methyl-quinolin-3-yl)-chromen-4-one (4d):
m.p.1730C. IR (KBr) cm-1: 1647(C=O), 1567, 1496(ring C=C). 1HNMR (300 MHz, DMSO):
δ 2.41 (s, 3H, CH3), 7.08 (s, 1H, CHOH), 7.40- δ8.10 (m, 6H, Ar-H). Anal. Calcd. for
C19H10O2NBrCl2 (435): C,52.41; H,2.29; N,3.21. Found: C,52.50; H,2.23; N,3.27.

2-(2-Chloro-6-methyl-quinolin-3-yl)-7-hydroxy-6,8-diiodo-chromen-4-one (4e):
m.p.1800C.IR (KBr) cm-1: 3409(-OH), 1639(C=O), 1570, 1489 (ring C=C). 1HNMR (300
MHz, DMSO): δ 2.43 (s, 3H, CH3), 7.05 (s, 1H, CHOH), 7.38- δ8.19 (m, 5H, Ar-H), 10.96(s,
1H, Ar-OH). Anal. Calcd. for C19H10O3NI2Cl (589.5): C,38.67; H,2.37; N,2.36.Found:
C,38.74; H,1.75; N,2.39.

6,8-Dichloro-2--(2-Chloro-6-methyl-quinolin-3-yl)-7-hydroxy-chromen-4-one(4f):
m.p. 2010C. IR (KBr) cm-1: 3401(-OH), 1644(C=O), 1581, 1489 (ring C=C). 1HNMR (300
MHz, DMSO): δ 2.41 (s, 3H, CH3), 7.06 (s, 1H, CHOH), 7.48- δ8.25 (m, 5H, Ar-H), 10.94(s,
1H, Ar-OH). Anal. Calcd. for C19H10O3NCl3 (406.5): C,56.06; H,2.46; N,3.44. Found:
C,55.97; H,2.51; N,3.37.

6,8-Dibromo-2-(2-Chloro-6-methyl-quinolin-3-yl)-7-hydroxy-chromen-4-one(4g):
m.p.1920C. IR (KBr) cm-1: 3400(-OH), 1648(C=O), 1567, 1488 (ring C=C). 1HNMR (300
MHz, DMSO): δ 2.45 (s, 3H, CH3), 7.02 (s, 1H, CHOH), 7.42- δ8.36 (m, 5H, Ar-H), 10.95(s,
1H, Ar-OH). Anal. Calcd. for C19H10O3NBr2Cl (495.5): C,46.01; H,2.01; N,2.82. Found:
C,45.94; H,2.06; N,2.74.

Table 1: Physical data of synthesized Flavones (4a-g)

Yield (%)
Reaction Period (min.)
Compound
Method A Method B Method A Method B
code
(min.) (min.)
4a 40 4.5 71 85
4b 35 5 63 87
4c 30 3.5 58 92
4d 40 3 69 96
4e 30 3.5 70 90
4f 40 4.5 68 88
4g 35 3.5 75 90

Antibacterial screening
The antibacterial activity of newly synthesized compounds (3a-g and 4a-g) was determined
by agar diffusion method[22]. The compounds were evaluated for antibacterial activity was
against Xanthomanas citri (Xc), Ervinia carotovara (Ec), Escherichia coli (E. coli) and
Bacillus subtilis (Bs).The antibiotic Ampicillin (100µg/mL) was used as standard antibiotic

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and 1% DMSO was used as solvent control. The culture strains of bacteria were maintained
on nutrient agar slant at 37±0.5oC for 24 h. The antibacterial activity was evaluated using
nutrient agar plate seeded with 0.1 mL of respective bacterial culture strain suspension
prepared in sterial saline (0.85%) of 105 CUF/ mL dilution. The wells of 6mm diameter were
filled with 0.1 mL of solution at fixed concentration 100µg/mL separately for each bacterial
strain. All the plates were incubated at 37±0.5oC for 24 h. The zone of inhibition of
compounds was measured using mm scale.

Table 2: Antibacterial activity data of synthesized compounds

Compound Zone of inhibition (mm)

code B. subtilis E. coli X. citri E.
carotovara
3a 16 18 16 20
3b 15 10 12 19
3c 11 13 17 09
3d 14 17 10 13
3e 26 25 23 24
3f 28 28 27 29
3g 25 28 26 27
4a 11 16 10 12
4b 23 22 18 21
4c 14 19 12 15
4d 13 14 13 12
4e 25 27 26 24
4f 27 25 21 29
4g 24 27 25 27
Control ---- ---- ---- ----
µg/mL)
Std(100µ 25 26 25 27

Germination Assay
The newly synthesized compounds were tested for effect on seed germination of wheat
(Triticum aestivum) by using moist blotter plate method[23]. In this method ten seeds of
wheat were arranged on the blotter paper (8.5cm) in pre sterilized Petri plates (10cm). The
control was treated with only distilled water, then, 2ml (0.01%) of each solution and distilled
water were added to the seeds on the blotter paper. The experiments were carried out under
natural light and at room temperature for ten days. The seed germination in the form of root
length and shoot length were measured (in cm) at the end of experiment.

Table 3: Effect of synthesized compounds on seed germination of Wheat (Triticum aestivum)

Compound Seed germination of wheat

code (cm)
Mean of Mean of root
shoot length length
3a 5.4 6.0
3b 6.5 10.5
3c 6.1 9.8

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3d 11.3 10.1
3e 5.0 12.4
3f 5.9 4.9
3g 5.5 10.3
4a 8.6 8.8
4b 5.0 6.1
4c 6.4 10.0
4d 5.1 6.6
4e 8.8 5.3
4f 5.0 6.0
4g 7.7 6.9
Control 4.9 6.0

Conclusion

In summary, we have synthesized some bioactive chalcones having 2-chloro-6-methyl

quinolinyl moiety and convert them into flavones by using conventional method as well as
microwave irradiation. Short reaction time, clean reaction with high yield (85-96%) than
conventional method is the advantages of microwave irradiation method. The antibacterial
study show that compound 3e, 3f, 3g,4b, 4e, 4f and 4g were found to be more active as
compared with standard drug and all new synthesized compounds were acting as a growth
promoting agents in seed germination of wheat.

Acknowledgement
Authors are also grateful to UGC New Delhi for sanctioning Major Research Grant and the
Director, IICT, Hyderabad for providing spectral analysis of newly synthesized compounds.
The authors are thankful to Principal, Yeshwant Mahavidyalaya, Nanded for providing
laboratory facilities.

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