Novel diazenyl chalcones with a 2-arylidene hydrazineylidene thiazole moiety: synthesis, anticancer potential,...

A series of diazenyl chalcones bearing 2-arylidene-hydrazinylidene thiazole units (4-6a,b) were designed, synthesised, and fully characterised by NMR, IR, MS, and UV spectroscopy. The compounds were evaluated for cytotoxicity against normal skin cells and the MDA and HepG2 cancer cell lines. The results reveal that most synthetic chemicals exhibited limited toxicity on normal cells at concentrations of 100 µg mL^-1 or below. Additionally, all pharmaceuticals, except for compound 4a, all pharmaceuticals demonstrated antiproliferation activity at quantities below the safety threshold. MDA and HepG2 cells exhibited no significant differences in cytotoxicity; however, compounds 5b and 6a showed the highest selectivity indices. The new compounds exhibited excellent affinity for the MMP-2 receptor, with values between -32.67 and -14.98 kcal mol^-1. Compounds 6a and 6b demonstrated the most advantageous results, with values of -32.67 and -32.27 kcal mol^-1, respectively, in comparison to the ligand's value of -33.73 kcal mol^-1. Compound 5b attained a third-place ranking with a score of -29.72 kcal mol^-1. Compounds 4a and 4b demonstrated relatively lower scores; however, compound 5a revealed markedly worse performance in comparison to other derivatives. Finally, these findings should be regarded as preliminary, indicating promising biological potential but not confirming any specific mechanism of action.