Synthesis and in vitro antimicrobial and antitumor activity of some nitrogen heterocycles

Resumo

5-Phenyl-2-[(3,4,5-trimethoxybenzylidene)hydrazino]-thiazole and 3-[(3,4,5-trimethoxybenzylidene)amino]-4-oxoimidazolidin-2-thione were prepared by cyclization of 1-[(3,4,5-trimethoxybenzyliden)amino]-thiourea with phenacyl bromide and ethyl chloroacetate in the presence of fused sodium acetate. Acetylation of the synthesized compounds with acetic anhydride gave corresponding N-acetyl derivatives. Condensation of the synthesized thione with aromatic aldehydes yielded two 3-substituted 5-arylidene-4oxo-imidazolidin-2-thiones. Acetylation of the latter compounds with acetic anhydride afforded the corresponding N-acetyl-4-oxo-imidazolidin-2-thiones. Some of the synthesized compounds exhibited antimicrobial activity. The cytotoxic activity of the prepared thiazole and imidazolidin-2-thione derivatives was studied on several tumor cell lines.