Synthesis of thiazole clubbed pyrazole derivatives as apoptosis inducers and anti-infective agents

Abstract

Fourteen N-[{(substituted-phenylthiazol-2-yl)-3-aryl-1H-pyrazol-4-yl}methylene]-5-substituted-thiazol-2-amine (5a-n) analogs were synthesized by the reaction of 3-aryl-1-(thiazol-2-yl)-1H-pyrazole-4-carbaldehyde and substituted thiazole amines. The structures of prepared compounds were delineated by elemental analysis, FT-IR and 1H NMR spectra. These analogs were scrutinized for in vitro anti-infective and cytotoxic activities. Some thaizole clubbed pyrazole derivatives were assessed for their cytological changes in germ cells of Capra hircus by using histomorphological analysis, fluorescence assay and apoptosis quantification. Compound 5l having 4-NO2 substituent induced the significant apoptosis in tested cells of Capra hircus. The results revealed that compounds 5c, 5e, 5k, and 5l have commendable antibacterial activity within MIC range of 62.5–250 μg/ml. Compound 5c emerged as a potent antimalarial compound by exhibiting IC50 value of 0.23 μg/ml and compound 5j induced paralysis of Pherentima posthuma at 8.6 ± 1.94 min and death at 20 ± 5.04 min, respectively. Compound 5j revealed an excellent cytotoxicity at IC50 value of 30.7 and < 10 μg/ml against MCF-7 and HeLa cells, respectively. Individually, compounds 5c, 5j and 5l could be considered as promising anti-infective and cytotoxic compounds.