Design, synthesis, X-ray analysis, and biological screening of new oxime and enaminone thiazoline-2-thione derivatives

Abstract

ABSTRACT An urgent need exists to develop antimicrobial and anticancer drugs that are safer and less prone to the development of resistance. To this end, a series of 12 new thiazoline-2-thione derivatives (oxime and enaminone) were synthesized using an appropriate synthetic route. The characterization of the newly synthesized compounds was performed using X-ray single-crystal diffractometry, elemental analysis, 1H NMR, 13C NMR, IR, and MS techniques. These compounds were then evaluated for their biological activities against a variety of microbes and human cancer cell lines. Our results revealed that the prepared thiazoline derivatives 4a, 4b, 6a, 6c, and 7 showed potent antifungal activity against Aspergillus fumigatus, comparable to the standard drugs. Additionally, all the thiazoline derivatives, except compound 4b, were effective against Candida albicans. The tested thiazolines also demonstrated potent antibacterial activity comparable to the standard drugs for all tested Gram-positive and Gram-negative bacterial species. The cytotoxicity evaluation of synthesized compounds 3, 6b and 7 against two cancer cell lines (HCT-116 and HepG-2) revealed that they had moderate cytotoxic activities, with compound 6b showing the best cytotoxic activity against the HCT-116 (IC50 = 79 µg/ml) and HepG-2 (IC50 = 49 µg/ml) cell lines. These findings open the pathway for the development of new lead compounds with chemotherapeutic properties.