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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, IC50 = 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 (κα1) and valence zero order molecular connectivity index (0χv) in describing antimicrobial activity, LUMO and κα2 in describing anticancer activity of 1-[4-(substituted phenyl)-2-(substituted phenyl azomethyl)-benzo[b]-[1,4]diazepin-1-yl]-2-substituted phenylaminoethanones. Keywords: Benzodiazepines, QSAR, Antibacterial, Antifungal, Anticancer