Investigation of anticancer potencies of newly generated Schiff base imidazolylphenylheterocyclic-2-ylmethylenethiazole-2-amines

Abstract

A new series of multi-heterocyclic Schiff base was constructed starting from 4'-(imidazol-1-yl)acetophenone which was converted to its 2-bromoethanone precursor which on cyclic condensation with thiourea yielded final thiazol-2-amine intermediate (3) to be reacted with substituted aldehydes to generate final imidazolylphenylheterocyclic-2-ylmethylenethiazole-2-amines (4a-4i). New Schiff base was investigated for their in vitro cytotoxic efficacies against a panel of three human cancer cell lines namely, MCF7 (human breast cancer), HCT116 (human colon cancer), and DU145 (human prostate cancer) and one normal skin fibroblast (SF). Most of these synthetic derivatives shown important cytotoxic actions against individual carcinoma cell line collections, but weak actions against SF, which is as anticipated. Observations of SAR suggested that the difference in the characteristics of substituents attached to the Schiff base function leads to the interesting variations within pharmacological effects of resultant molecular systems. Structural analysis performed using FT-IR, H-1 NMR, C-13 NMR spectroscopy and CHN analysis for final potent anticancer Schiff base, which warrant further investigations. (C) 2016 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.