N′-[4-[(Substituted imino)methyl]benzylidene]-substituted benzohydrazides: synthesis, antimicrobial, antiviral, and anticancer evaluation, and QSAR studies

Kumar, Pradeep; Narasimhan, Balasubramanian; Ramasamy, Kalavathy; Mani, Vasudevan; Mishra, Rakesh Kumar; Majeed, Abu Bakar Abdul; De Clercq, Erik

ABSTRACT: A variety of N′-[4-[(substituted imino)methyl]benzylidene]-substituted benzohydrazides have been synthesized and evaluated for antimicrobial and anticancer potential. Results from testing of antimicrobial activity indicated the most potent antimicrobial agents had pMIC (am) = 1.51. The synthesized compounds were bacteriostatic and fungistatic in action. Results from evaluation of antiviral activity indicated that none of the synthesized hydrazide derivatives inhibited viral replication at sub-toxic concentrations. Results from anti-HIV screening against HIV-2 strain ROD indicated that one compound was more potent (IC (50) ≥ 1 μg/cm(3)) than the standard drug nevirapine (IC (50) ≥ 4 μg/cm(3)) and another was equipotent (IC (50) ≥ 4 μg/cm(3)). The most effective anticancer agent against both HCT116 and MCF7 cancer cell lines had IC (50) = 19 and 18 μg/cm(3), respectively. QSAR analysis indicated the importance of Wiener index (W) and energy of the lowest unoccupied molecular orbital (LUMO) in describing the antimicrobial activity of the synthesized compounds. GRAPHICAL ABSTRACT: [Image: see text]