Abstract
A series of 1-[4-(substituted phenyl)-2-(substituted phenyl azomethyl)-benzo[b]-[1,4]diaze pin-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-C hloro-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-dimethylaminophenyl)-2-(p-tolylazo-methyl)-benzo[b][1,4]diazepin-1-yl]-2-phenyl aminoethanone (1, IC50 = 1.42 mu M/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 (kappa alpha(1)) and valence zero order molecular connectivity index ((0)chi(v)) in describing antimicrobial activity, LUMO and kappa alpha(2) in describing anticancer activity of 1-[4-(substituted phenyl)-2-(substituted phenyl azomethyl)-benzo[b]-[1,4]diazepin-1-yl]-2-substitu ted phenylaminoethanones. (C) 2015 The Authors. Published by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).