Synthesis, in vitro antioxidant, anticancer activity and molecular docking of new thiazole derivatives

Nitrogen and sulfur-containing heterocyclic aromatic derivatives play an enormous and important role in the field of medicine and in synthesis of pharmaceutically active compounds. In this study, a series of new 2-[1-(1,3-diphenyl-1H-pyrazol-4-yl)ethylidene]hydrazinyl)-4-methyl-5-aryldiazinyl)-thiazole derivatives (9a–d) was synthesized by an efficient and convenient method by reacting hydrazonoyl chloride derivatives (4) with carbothioamide derivative (3). The structures of these compounds were elucidated using elemental analyses, spectroscopic analyses (IR, NMR, Mass spectrometer) and computational measurements. Density functional theory (DFT) is performed to get the optimized structures with minimization Energy. The main goal of preparing these compounds is to evaluate their in vitro antioxidant and anticancer activities after studying their molecular docking. The docking was performed on compounds (9a–d) against tyrosine kinase (PDB ID: 2HCK). The results revealed that all docked compounds (9a-d) have a higher binding energy, ranging from −7.56 to −8,89 kcal/mol. compared to the original ligand quercetin, which was −5.92 kcal/mol. Moreover, the results of antioxidant and anticancer activity assay methods demonstrated that the tested derivatives (9a-d) exhibited potent antioxidant and anti-tumor activities against HepG2 cell lines.