Synthesis, and Cytotoxic Activity of Novel Pyrazoline-Thiazolidinone Derivatives with Molecular Docking Studies

Abstract

1-(4-substitutesd)-2-(5-phenyl-3-(1H-pyrrol-2-yl)-4,5-dihydropyrazol-1-yl)thiazol-5-yl)-2-aryldiazene 9a-f were prepared through reactions of 5-phenyl-3-(1H-pyrrol-2-yl)-4, 5-dihydropyrazole-1-carbothioamide 5 with hydrazonoyl halides. Furthermore, thioamide 5 was utilized as starting materials for thiazolidone synthesis 10 and arylidene thiazoles 15a–c. Also pyran derivatives 12a-b, 13a-b,14a-b and thioanilide derivaives 16 were obtained from the reaction of thiazilidone 10 with arylidenemalononitrile and phenyl isothiocyanat, respectively. When possible, the structures of experimentally synthesized compounds were identified by elemental analysis, spectral analysis, and alternative synthesis routes. Some of the synthesized compounds as 9f, 10, 12b, and 16 were screened for their cytotoxicity against MCF-7 and HCT-116 cells using the MTT assay. They exhibited remarkable cytotoxic activities with promising IC50 values. Interestingly, compound 16 exhibited potent cytotoxicity against MCF-7 and HCT-116 with IC50 values of 5.05 and 3.08 μM, compared to doxorubicin with IC50 values of 7.27 and 8.92 μM, respectively show interesting biological activities as anticancer activities. Additionally, the tested compounds were nontoxic against WISH cells with higher IC50 values. Hence, these compounds may serve as potent and selective cytotoxic agents.