Synthesis and anticancer (MCF-7, PC-3) activities of new 2-hydroxy-2,2-bis(4-substitutedphenyl)-N'-[(1E)-(3/4- substitutedphenyl)methylene]-acetohydrazides

Abstract

A series of five –CH3, -NO2, -OCH3 and -Cl substituted 2-hydroxy-2,2-bis(4-phenyl)-N'-[(1E)-(3/4phenyl)methylene]acetohydrazide (1a-1e) was synthesized by the reaction of 2-hydroxy-2,2-diphenylacetohydrazide with substituted aromatic aldehydes to give intermediate Schiff bases. Structures of the synthesized compounds were characterized using NMR (1D; 1H, 13C/APT and 2D 1H-1H COSY, and NOESY), FT-IR, UV, LC-MS/MS spectral data and elemental analysis. The geometry of compounds 1a-1e were determined to be “E” by NOESY. All the tested compounds showed cytotoxic activity on MCF-7 and PC-3 cell line at highest experimental concentration (100 μM). Compounds 1b (18.24 ± 7.62 μM) and 1e (7.62 ± 1.85 μM) have strong anti-proliferative activity on MCF-7 cell line, while compound 1b (45.81 ± 1.10 μM) has the strongest activity on PC-3 cell line.