Deepak Verma, Pradeep Kumar, B. Narasimhan
Jun 17, 2015
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Influential Citations
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Journal
Arabian Journal of Chemistry
Abstract
Abstract A series of 1-[4-(substituted phenyl)-2-(substituted phenyl azomethyl)-benzo[ b ]-[1,4]diazepin-1-yl]-2-substituted phenylaminoethanones ( 1–17 ) was synthesized and evaluated in vitro for its antimicrobial and anticancer activities. Results of antimicrobial screening indicated that 1-[4-[4-Chloro-phenyl)-2-[(3-nitro-phenylazo)-methyl]-benzo[ b ][1,4]diazepin-1-yl]-2-(2-methyl-5-nitro-phenyl amino)-ethanone ( 16 ) and 1-[4-(3,4-dimethoxy-phenyl)-2-[(4-nitro-phenylazo)-methyl]-benzo[ b ][1,4]diazepin-1-yl]-2-(3-nitrophenylamino)-ethanone ( 17 ) were found to be the most effective antimicrobial agents. The anticancer screening results indicated that 1-[4-(4-dimethylamino-phenyl)-2-( p- tolylazo-methyl)-benzo[b][1,4]diazepin-1-yl]-2-phenyl aminoethanone ( 1 , IC 50 = 1.42 μM/mL against HCT 116 cancer cell lines) was the most potent anticancer agent and was more potent than 5-FU. The results of QSAR studies demonstrated the importance of topological parameters, Kier’s alpha first order shape index ( κα 1 ) and valence zero order molecular connectivity index ( 0 χ v ) in describing antimicrobial activity, LUMO and κα 2 in describing anticancer activity of 1-[4-(substituted phenyl)-2-(substituted phenyl azomethyl)-benzo[ b ]-[1,4]diazepin-1-yl]-2-substituted phenylaminoethanones.