Prasadarao.

K*

et al. /International Journal Of Pharmacy&Technology

IJPT | April-2012 | Vol. 4 | Issue No.1 | 4060-4066 Page 4060
ISSN: 0975-766X
CODEN: IJPTFI
Available Online through Research Article
www.ijptonline.com
SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL ACTIVITY OF SOME CHALCONES
Prasadarao.K*, Mohan.S
Dept. of Chemistry, Bapatla Engineering College, Bapatla 522101, Andhra Pradesh, India.
Email: prasad17467@gmail.com
Received on 15-03-2012 Accepted on 28-03-2012
Abstract
Chalcones are the important constituent of many natural sources and have variety of biological activities. The
compounds are synthesized by Claisen- Schmidt base catalyzed condensation of parachloroacetophenone with
benzaldehyde and parahydroxybenzaldehyde .The structures of the synthesized compounds were confirmed by
elemental analysis, IR,
1
H NMR spectroscopic data. The antimicrobial activities of these compounds were evaluated
by filter paper disc plate method.
Keywords: Chalcones, Parachloroacetophenone, Benzaldehyde, Parahydroxybenzaldehyde, Antimicrobial activity.
Introduction
The Chemistry of chalcones has generated intensive scientific studies throughout the world. Especially interest
has been focused on the synthesis and biodynamic activities of chalcones. The name Chalcone was given by
kostanecki and tambor
1
. These compounds are precursors of flavonoids and isoflavonoids which are abundant in
plants. Various biological activities are associated with chalcones, such as anticancer
2
, antitumor
3
, antioxidant
4
and
antimalarial
5
. The presence of naphthyl ring in chalcones has shown promising antimicrobial and antihyperglycemic
activity
6, 7
. These are used to synthesize several derivatives like cyanopyridines, pyrazolines, isoxazoles and
pyrimidines having different heterocyclic ring systems
8-11.
The most convenient methods are the Claisen-Schmidt
condensation of equimolar quantities of an arylmethylketones with aryl aldehyde in the presence of alcoholic alkali
12
.
The chalcones (1, 3-diaryl-2-propenones) and their derivatives are important intermediates in organic synthesis
13-15
.
In the present communication we report the reaction of parachloroacetophenone with benzaldehyde and
Prasadarao.K*

et al. /International Journal Of Pharmacy&Technology

IJPT | April-2012 | Vol. 4 | Issue No.1 | 4060-4066 Page 4061
parahydroxybenzaldehyde in the presence of sodium hydroxide solution at room temperature. The structures of the
synthesized compounds are elucidated on the basis of their elemental analysis, IR and
1
H NMR spectral studies these
are also screened for their antimicrobial activity.
Materials and Methods
All the products were synthesized and characterized by their spectral analysis. The chemicals, 4-
chloroacetophenone, benzaldehyde, 4-hydroxybenzaldehyde, sodium hydroxide, hydrochloric acid, and ethanol were
purchased from either E- Merk or Qualigens (AR quality) reagents, pure distilled solvents were used throughout the
work. Ethanol (Bengal, B.P, 78
0
C) was refluxed with calcium oxide for 6 hours and allowed to stand overnight.
Later, it was distilled and distillate was fractionated over sodium ethoxide. Melting points were determined in an
open capillary tube and are uncorrected. IR spectra were recorded in KBr on a JASCO FT/IR-5300. 1H NMR spectra
were recorded on Brucker spectrometer at 300MHz in CdCl3, (900W).
Elemental analysis was carried out on a Flash Ea 1112 Series Chn Report Thermo Finnigan. Chalcones were
synthesized by Clasien- Schmidt condensation
16
using ethanol as reaction solvent. The chemicals and solvents used
were of laboratory grade and were purified. Completion of the reaction was monitored by thin layer chromatography
(TLC) on pre-coated sheets of silica gel-G (Merck, Germany) using iodine vapour for detection. Column
chromatography was performed on silica gel (Merck, 60-120 mesh). The synthetic pathway is presented in Scheme 1
and physicochemical data and spectroscopic data for the synthesized compounds are given Table a) and Table b).


Prasadarao.K*

et al. /International Journal Of Pharmacy&Technology

IJPT | April-2012 | Vol. 4 | Issue No.1 | 4060-4066 Page 4062
(1) Synthesis of 4-chloro chalcone
An equimolar mixture of 2.2gm (1.8ml, 0.0125 moles) p-chloroacetophenone and 1.6gm (0.0125 moles)
benzaldehyde are dissolved in ethanol in 150 ml conical flask. The mixture was stirred with a magnetic stirrer and 16
ml of NaOH (50%) was added drop wise into it. The mixture was stirred at room temperature until it was solidified.
After the completion of the reaction (monitored by TLC), the crude mixture was poured into ice water and then
acidified the product with 10%HCl solution in cold condition. The bright yellow coloured compound was collected
on a Buckner funnel under suction pump. The solid is washed with water thoroughly and dried and recrystallised
from absolute ethanol to give 4-chlorochalcone (1) as light yellow solids.
O
Cl

(2) Synthesis of 4- chloro, 4- hydroxy chalcone
Reaction with parachloroacetophenone (2.2gm) and parahydroxy benzaldehyde (2 gm); 4-chloro, 4-hydroxy
chalcone (2) was obtained by the above described procedure.
O
Cl
OH

Results and discussions

Prasadarao.K*

et al. /International Journal Of Pharmacy&Technology

IJPT | April-2012 | Vol. 4 | Issue No.1 | 4060-4066 Page 4063
Table: a) physicochemical data of Chalcones






The Claisen-Schmidt condensation is an important C-C bond formation for the synthesis of 1, 3-diaryl-2-propen-1-
ones (chalcones). It is generally carried out of the use of strong bases such as NaOH or KOH in polar solvents
(MeOH or DMF). Synthesis of chalcone is a single step method. The synthesized chalcone derivatives were
undergone physicochemical characterization and the obtained results are given in Table.1. The yields of the
synthesized compounds were found to be significant. The structure of the synthesized compounds was confirmed by
IR, Mass and elemental analysis. Elemental analysis showed that the percentage of the carbon, hydrogen, Chlorine
and oxyzen was found experimentally is equivalent to the calculated values in all compounds. All the compounds
give the characteristic IR and peak that proved that the presence of particular functional group (Table b), and
1
H
NMR helps to find the different types of protons present in the structure.
4-chloro chalcone have the molecular formula of C
15
H
11
OCl. The IR band at 1654.6cm-
1
suggesting the
presence of (C=O) group. The IR band at 1589.5 cm-
1
indicates that the presence of (C=C) (olifinic) group. IR band
at 1565.9 cm-
1
& 1444 cm-
1
indicates presence of (C=C) (aromatic) group. The IR band at 2310.6 cm-
1
suggesting the
presence of (C-H) group. Melting point of the compound is 98C which is uncorrected.
The molecular formula of 4-chloro, 4-hydroxy chalcone is C
15
H
11
O
2
Cl. The IR band at 1653.5 cm-
1
suggesting the presence of (C=O) group. The IR band at 1586.0cm-
1
indicates that the presence of (C=C) (olifinic)
group. IR band at 1575 cm-
1
& 1425 cm-
1
indicates presence of (C=C) (aromatic) group. The IR band at 2340.5 cm-
1
suggesting the presence of (C-H) group. Melting point of the compound is 103C which is uncorrected.

Comd M.F.
Yield
%
M.W
M.P
0
C
ElementalAnalysis
C H Cl O
%
Found
%
calcd
%
Found
%
calcd
%
Found
%
calcd
%
Found
%
calcd
1
C
15
H
11
OCl 86 242.5 98 74.0 74.2 4.4 4.5 14.2 14.6 6.6 6.7
2
C
15
H
11
O
2
Cl 89 258.5 103 69.3 69.6 4.1 4.2 13.3 13.7 12.4 12.5
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et al. /International Journal Of Pharmacy&Technology

IJPT | April-2012 | Vol. 4 | Issue No.1 | 4060-4066 Page 4064
Table: b) Spectral data of the Chalcones
S.No Compound
IR (cm
-1
)
(C=O), (C=C) (C=C), (C-H)
(Olef) (aroma)
PMR( ppm)
1
4-chloro
chalcone
1654.6 1589.5 1565.9 2310.6
1444
7.3-8.19 (m, 5H)
8.1(d,2H,6H,J= 8.6Hz)
6.9(d,J=8.7 ,3H&4H)
7.48(1H,S,H-);7.85(1H,d,J=15.6 ,H-)
2
4-chloro, 4-
hydroxy
chalcone
1653.5 1586.0 1575 2340.5
1425
7.95(d,2H,6H,J= 7.9 Hz)
6.95 (d,3H,&5H,J= 8.6 Hz)
7.85(d,2H,&6H,J= 8.35 Hz)
7.25 (d,3H,&5H,J= 8.35 Hz)
7.42 (S,1H,H-); 7.82 (S,1H, H-)

Table: c) Antimicrobial data of compounds
S.no compounds
Mean zone of inhibition (in cm )
Xanthomonas
campestris
Agrobacterium tumifaciens
1 4-chloro chalcone 0.8 1.0
2
4-chloro,4-hydroxy
chalcone
0.3 0.9

Antimicrobial activity
Compounds with electron releasing groups such as hydroxyl and methoxy showed better antibacterial activity
than the others not having such groups. Compounds having pharmachophores such as chloro, dichloro and fluoro
groups have exhibited more antifungal activity on all the three fungi than the others. Chalcone derivatives with these
substituents showing greater antimicrobial activity
17
.
Prasadarao.K*

et al. /International Journal Of Pharmacy&Technology

IJPT | April-2012 | Vol. 4 | Issue No.1 | 4060-4066 Page 4065
The synthesized compounds were screened for their in vitro Antimicrobial activity against Xanthomonas
campestris, Agrobacterium tumifaciens by measuring the zone of inhibition in cm.The antimicrobial activity was
performed by filter paper disc plate method
18, 19
. The agar mediums were purchased from HI media Laboratories
Ltd., Mumbai, India, and reporet in Table: c) . Muller Hinton agar & Sabouroud Dextrose agar were employed as
culture medium and DMSO were used as solvent control for antimicrobial activity.
Conclusion
The synthesized substituted Chalcones were characterized by TLC, melting point, IR,
1
H NMR spectral studies
and Elemental analysis. From the antimicrobial screening it was observed that all the compounds exhibited activity
against all the organisms employed. The results obtained from this study confirmed that the product has formed.
Hence forth viewing these characteristic properties more compounds can be synthesized and subjected to
pharmacological evaluation.
Acknowledgements
Authors are thankful to Mr. K.M.K. Reddy, Dept. of Biotechnology, Bapatla Engineering College, Bapatla for their
help in antimicrobial study and LAILA IMPEX Research Center, Vijayawada for
1
H- NMR spectra and IR spectra.
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Corresponding Author:
K. Prasadarao*
Email: prasad17467@gmail.com