Synthesis of 2-, 3- or 4-phenylsubtituted Chalcones Based on 4- phenylamino-6-nitro-2-[(E)-2-phenylvinyl]quinoline, Evaluation of their Antimicrobial and Antifungal Activity

Author(s): Sulochana Mudaliar, Kishor H. Chikhalia, Nisha K. Shah

Journal Name: Letters in Drug Design & Discovery

Volume 13 , Issue 8 , 2016


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Abstract:

A series of thirteen (2E)-1-[4-({6-nitro-2-[(E)-2-phenylvinyl]quinolin-4-yl}amino)phenyl]- 3-[(substituted) phenyl]prop-2-en-1-ones (5a-5m) were synthesized by five-step synthesis starting from 4-nitroaniline via 2-methyl-6-nitroquinolin-4-ol (2), 4-chloro-2-methyl-6-nitroquinoline (3), 4- chloro-6-nitro-2-[(E)-2-phenylethenyl]quinoline (3), and 1-[4-({6-nitro-2-[(E)-2-phenylvinyl]quinolin- 4-yl}amino)phenyl]ethanone (5), respectively. Final chalcones 6a-6m were synthetized from 4 by condensation reaction with corresponding benzaldehydes (unsubstituted, 2-, 3- and 4-methyl-, 2-, 3- and 4-methoxy-, 2- and 4-fluoro-, 2-, 3- and 4-chloro-, and 4-trifluoromethylbenzaldehyde, respectively). Chalcones 6a-6m were characterized by IR, 1H NMR and MS spectroscopy deflate, is not presented. Antimicrobial and antifungal activity of the compound 6 was studied against the four bacterial types (Staphylococcus aureus MTCC 96, Streptococcus pyogenes MTCC 443, Escherichia coli MTCC 442, Pseudomonas aeruginosa MTCC 441) and three different types fungal strains (Aspergillus niger MTCC 282, Aspergillus clavatus MTCC1323, Candida albicans MTCC 227). From the above synthesized compounds the chalcones 6e, 6f, 6k, and 6m exhibited very good activity against studied gram-positive and gram-negative bacterial strains and compounds 6a, 6e, 6f, 6j 6k and 6m showed very good anti-fungal activity against fungi above.

Keywords: Chalcone, quinoline, antibacterial, claisen–schmidt condensation, benzaldehyde, 4-aminoacetophenone.

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Article Details

VOLUME: 13
ISSUE: 8
Year: 2016
Published on: 25 August, 2016
Page: [818 - 823]
Pages: 6
DOI: 10.2174/1570180812666151016205033
Price: $65

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