The synthesis of new thiazole derivatives and their biological activity studies

In medicinal chemistry, new thiazolyl hydrazone derivatives have gained importance in antifungal and anticancer drug design and development. In the current study, new thiazolyl hydrazone derivatives bearing quinoline ring were synthesized. The structures of the obtained compounds were elucidated by IR, 1H NMR, 13C NMR, mass spectra and elemental analysis. The anticandidal effects of the synthesized compounds were evaluated using disc diffusion method. Besides, the cytotoxic effects of these compounds on A549 human lung adenocarcinoma, HepG2 human hepatocellular carcinoma, MCF-7 human breast adenocarcinoma and NIH/3T3 mouse embryonic fibroblast (healthy) cell lines were investigated using MTT assay. 4-(4-Fluorophenyl)-2-(2-((quinolin-4-yl)methylene)hydrazinyl)thiazole (4) showed antifungal activity against Candida albicans and Candida krusei in the concentration of 1 mg/mL. Due to its anticandidal activity, Ames MPF genotoxicity assay was applied to compound 4. In MTT and Ames MPF tests, it was determined that compound 4 did not show cytotoxic and genotoxic effects. It was determined that 4-(naphthalen-2-yl)-2-(2-((quinolin-4-yl)methylene)hydrazinyl)thiazole (10) showed more selective anticancer activity than positive control cisplatin against A549 and MCF-7 cell lines. Besides, 4-(4-chlorophenyl)-2-(2-((quinolin-4-yl)methylene)hydrazinyl)thiazole (5) exhibited more selective anticancer activity than cisplatin against HepG2 cell line. Due to their high selectivity index, these compounds are considered as candidate compounds to participate in advancing research.