Synthesis, Characterization, and Anticancer Activity of Some Thiazole and Imidazolidine Derivatives Containing Pyridine Moiety

Resumo

5-Phenyl-2-[(6-acetylpyridine-2-ylethylidene)hydrazino]thiazole 4 and 1-[(6-acetylpyrid-ine-2-ylethylidene)amino]-2-thioxoimidazolidine-4-one 6 are synthesized by cyclization of 1-[1-(6-acetylpyridin-2- yl)ethylidene]thiosemicarbazide 2 with phenacyl(ω)bromide or ethyl chloroacetate in the presence of fused sodium acetate. Reaction of compounds 2, 4, and 6 with acetic anhydride gives N-triacetyl derivative 3 and N-acetyl derivatives 5 and 7. Treatment of compound 6 with 4-methoxy benzaldehyde yields the corresponding carbanol derivative 8. Structures of the synthesized heterocyclic compounds are characterized by EI-MS and NMR spectroscopy. Antitumor activity of compounds 4, 6, 8, and 9 is evaluated against human breast carcinoma cell line (MCF-7).