Abstract
Reaction of 1-[4-(1,2-dihydro-1,5-dimethyl-2-phenyl-3-oxo-3H-pyrazol-4-yl)-2-phenylsulfonyl-1-ethanone (1) with phenyl isothiocyanate afforded the 4-(3-mercapto-3-(phenylamino)-2-(phenylsulfonyl)acryloyl)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (2). Treatment of compound 2 with hydrazonoyl chlorides 3a-h afforded the corresponding1,3,4-thiadiazole derivatives 5a-h. Cyclocondensation reaction of compound 2 with the appropriate -halo-compounds 6, 8, 10, 12a,b or 14 (ethyl 2-chloroacetate, chloroacetonitrile, 1-chloropropan-2-one, 2-bromo-1-phenylethanone, 2-bromo-1-p-tolylethanone, and 2-bromoacetyl-3H-benzo [f]chromen-3-one) afforded the 1,3-thiazole derivatives 7, 9, 11, 13a,b, and 15, respectively. Coupling of the ketosulphone 1 with the appropriate diazotized 4H-1,2,4-triazol-3-amine 16 and 2-aminobenzimidazole 19 afforded triazolo[5,1-c][1, 2, 4]triazine 18 and benzo[4,5]imidazo[2,1-c][1, 2, 4]triazine 21, respectively. The structures of the synthesized compounds were confirmed on the basis of their elemental analysis and spectral data and evaluated as potential anti-breast cancer agents. Moreover, the computational studies using MOE 2014.09 software are confirming the results in biological activity.