A number of substituted-α,β-unsaturated carbonyl compounds (1a-i) were prepared by Claisen-Schmidt condensation of substituted acetophenone with selected araldehydes, which on cycloaddition with thiourea furnished 4,6-disubstituted pyrimidine-2-thiols (2a-i). Reaction of (2a-i) with ethyl chloroacetate followed by condensation with hydrazine hydrate yielded 2-[(4,6-disubstituted pyrimidine-2-yl) thio] acetohydrazides (4a-c). Condensation of compounds (4a-c) with phenyl isothiocyanate gave 2-{[(4,6-disubstituted pyrimidine-2-yl) thio] acetyl}-N-phenylhydrazinecarbothioamides (5a-c) which on treatment with concentrated sulphuric acid afforded titled compounds 5-{(4,6-disubstituted pyrimidine-2-yl) thio] methyl}-N-phenyl-1,3,4-thiadiazole-2-amines (6a-c). These compounds have been characterized on the basis of elemental analysis, IR, 1H NMR and MS. Compounds have been evaluated for their anticancer and antioxidant activities. Compounds 2b, 2c and 6b exhibited significant antitumor activity against human breast cancer MCF 7 cell line. However, moderate antioxidant activity was observed with compounds 2c, 2d, 2g and 6b.
A series of copper(II) and cobalt(II) coordination compounds with 2-substituted benzimidazole derived monodentate and bidentate ligands have been prepared and characterized by microanalysis, IR and UV-Vis spectroscopy. Synthesized metal complexes have been screened for their in vitro antioxidant and antitumor activity. The complex 4a showed significant nitric oxide free radical scavenging activity (IC 50 65µg/ml), while 3i and 3g showed potent superoxide dismutase activity with IC 50 of 0.26 and 0.28 µM respectively. In vitro cytotoxicity study with human breast MCF-7 and CNS SF 268 cancer cell lines showed that the most active 2-benzyl-1H-benzimidazole Cu(II) complex 3a inhibited the growth of cancer cells at 20 µM concentration.
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