Synthesis, Characterization and Anti-Microbial Evaluation of Derivative of Chalcone
Gopi C.* and Dhanaraju M. D.
Research Lab, GIET School of Pharmacy, NH-5, Chaitanya Nagar, Rajahmundry-533294, India
*Corresponding Author E-mail: gopi.baid@yahoo.com
ABSTRACT:
To development of antimicrobial agents a series of chalcones were prepared by condensation of appropriate acetophenones with different aromatic aldehyde in the presence of alkali at 37°C. The synthesized compounds were characterized by IR, NMR spectral studies. The synthesized compounds were evaluated for anti-bacterial activity, and anti-fungal activity. The result had shown that anti-bacterial and anti-fungal activity of Compound containing electron withdrawing group (G2, G4, and G6).
KEYWORDS: chalcone, Aromatic aldehyde, acetophenone, anti-bacterial, anti-fungal
Chalcone constitute an impartment group of natural products and some of them possess a wide range of biological activities like analgesic1, antimicrobial2, anti-inflammatory3, antioxidant4, antiplatelet5, antimalarial6, anticancer7, antitubercular8, antihyperglycemic9, antiviral10, antileishmanial11, antiulcerative12 etc,. Based on the above pharmacological activity it is worthwhile to prepare newer compound for better activity against anti-bacterial and anti-fungal. The heterocyclic compound with the background of Chalcone intermediate shown very potent biological activity. Chalcone posses α-β unsaturated keto group in its structure, which is responsible for Anti microbial activity. In the presence work we report the reaction of acetophenone with different aromatic aldehyde by condensation to form chalcones. The synthesized compounds were ascertained from spectral analysis. Result of IR, NMR analysis conformed the synthesized derived chalcone.
MATERIALS AND METHODS:
General procedure for preparation of chalcone:
Acetophenone (0.01 mole) and Aromatic aldehyde are dissolve in 30ml of ethanol, and mixed with 15 ml of potassium hydroxide solution, kept it for overnight, this mixture is poured in to the beaker containing HCl and ice cube and water, chalcones were precipitated out which is separated by filtration process (Scheme- 1).
Scheme- 1
Table-1:- ZONE OF INHIBITION OF SYNTHESIZED COMPOUND (CONCENTRATION µg/ml-1)
|
COMPOUND
|
ZONE OF INHIBITION(mm) |
|||||||||||||||||||||
|
BACTERIA |
FUNGUS |
|||||||||||||||||||||
|
B.subtilis |
E.coli |
P.aeuruginosa |
S.aureus |
A.Fumigatus |
A.flavus |
|||||||||||||||||
|
10 |
50 |
100 |
10 |
50 |
100 |
10 |
50 |
100 |
10 |
50 |
100 |
50 |
50 |
|||||||||
|
G1 |
09 |
10 |
12 |
07 |
08 |
12 |
07 |
09 |
11 |
08 |
10 |
11 |
07 |
08 |
||||||||
|
G2 |
14 |
17 |
20 |
12 |
15 |
21 |
10 |
16 |
18 |
15 |
17 |
21 |
13 |
14 |
||||||||
|
G3 |
08 |
10 |
11 |
07 |
09 |
11 |
07 |
10 |
11 |
08 |
09 |
10 |
07 |
07 |
||||||||
|
G4 |
13 |
15 |
16 |
10 |
13 |
18 |
08 |
14 |
17 |
13 |
15 |
19 |
13 |
12 |
||||||||
|
G5 |
11 |
12 |
14 |
07 |
09 |
13 |
07 |
11 |
14 |
9 |
11 |
13 |
09 |
10 |
||||||||
|
G6 |
12 |
14 |
15 |
09 |
11 |
15 |
07 |
12 |
16 |
11 |
13 |
14 |
10 |
11 |
||||||||
|
STANDARE |
AMPICILLIN |
FLUCONAZOLE |
||||||||||||||||||||
|
16 |
20 |
24 |
14 |
20 |
24 |
15 |
21 |
24 |
21 |
22 |
25 |
17 |
17 |
|||||||||
RESULT:
Characterization of Synthesized Compound:
1, 5-diphenylpenta-2, 4-dien-1-one (G1):
Yield (74%), melting point-(370-375), IR spectroscopy (cm-1)- 1645(-C=O),1634(-CH=CH), 1H-NMR-(CDCl3,δ ppm): 7.89 (2H,d,=Ar), 7.22 (1H,d,=CO-CH),7.02-7.68 (8H,m,Ar-H), 6.73 (1H,d,-CH=CH),7.31(2H,d,-CH=CH).
3-(3-hydroxy-4-methoxyphenyl)-1-phenylprop-2-en-1-one (G2):
Yield (85%),melting point-(510-515), IR spectroscopy(cm-1)- 1670(-C=O),1645(-CH=CH),3645 (phenolic OH), 1280(-OCH3), 1H-NMR-(CDCl3,δ ppm): 7.2-7.9 (8H,m,=Ar),7.60 (1H,d,=CO-CH), 7.9 (1H,s,-CH=CH),3.5(3H,s,-OCH3),5.5(1H,s,OH).
3-(furan-2yl)-1-phenylprop-2en-1-one (G3):
Yield (68%),melting point-(362-367), IR spectroscopy(cm-1)- 1632(-C=O),1663(-CH=CH),1H-NMR-(CDCl3,δ ppm): 7.3-7.8 (8H,m,=Ar), 7.45 (1H,m,=CO-CH), 7.7 (1H,m,-CH=CH).
3-hydroxyphenyl-1-phenylprop-2-ene-1-one (G4):
Yield (92%), melting point-(460-470), IR spectroscopy(cm-1)- 1628(-C=O),1612(-CH=CH),3658 (phenolic OH), 1H-NMR-(CDCl3,δ ppm): 6.5-7.2 (9H,m,=Ar), 7.4 (1H,m,=CO-CH), 8.3 (1H,d,-CH=CH), 5.1(1H,s,OH).
3-4-(dimethyl amino) phenyl)-1-phenylprop-2-en-1-one (G5):
Yield (69%), melting point-(420-430), IR spectroscopy (cm-1)- 1687(-C=O),1616(-CH=CH),1324(N-(CH3)2) 1H-NMR-(CDCl3,δ ppm): 6.5-8.4 (9H,m,=Ar), 7.2 (1H,m,=CO-CH), 8.3 (1H,d,-CH=CH), 3.5(6H,d,-N(CH3)2.
1-phenyl-3-p-tolylprop-2-en-1-one (G6):
Yield (76%), melting point-(375-380), IR spectroscopy (cm-1)- 1662(-C=O),1637(-CH=CH), 36451H-NMR-(CDCl3,δ ppm): 7.0-8.2 (7H,m,=Ar), 7.2-7.3(2H,d,Ar-H)7.3 (1H,d,=CO-CH), 8.4 (1H,d,-CH=CH),2.7-2.8(3H,s,CH3)
Anti-microbial activity:
The synthesized compounds were screened against four bacteria, and two fungal organisms. Anti-microbial activity of the synthesized drug has been carried out by paper disc diffusion method13. The name of micro-organism used in the microbial study was B.subtilis, E.coli, P.aeuruginosa, P.aeuruginosa, A.Fumigatus, and A.flavus. The sterilized medium was inoculated with the suspension of the micro-organism and poured into a petridish to give a depth of 3-4mm. The paper impregnated with the synthesised compounds (10, 50, 100µg ml-1 in dimethyl formamide) was placed on the solidified medium. The plates were pre-incubated for 1 hour at RT and incubated at 37◦C for 24 and 48 hour for anti-bacterial and anti-bacterial and anti-fungal activities, respectively. Ampicilline (10, 50,100µg/disc) and Fluconazole (50µg/disc) were used as standard for anti-bacterial and anti-fungal activities.
DISCUSSION:
Compounds (G2, G4, and G6) contain electron releasing group such as methoxy, hydroxyl, methyl, were showed significant anti-bacterial and anti-fungal activity than the other group. The α-β unsaturated keto functional group may be activated by presence of electron releasing group. Compound (G5) showing moderate activity, whereas (G1, G3) shown mild activity against bacteria and fungus (table-1).
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Received on 15.09.2010 Modified on 12.10.2010
Accepted on 30.10.2010 © AJRC All right reserved
Asian J. Research Chem. 4(2): February 2011; Page 181-182