Synthesis and cytotoxicity evaluation of some novel tetrahydronaphthalene-pyrazole derivatives

Abstract

1-(1,2,3,4-Tetrahydronaphthalen-6-yl)-3-(1,3-diphenyl-1H-pyrazol-4-yl)prop-2-en-1-one (3) was synthesized and then treated with various hydrazine hydrate derivatives to afford the corresponding dihydropyrazoles 4-9, respectively. Condensation of pyrazole carbothioamide 9 with á-haloketones yielded the corresponding thiazole derivatives 10a, b. Also, the reaction of the chalcone 3 with various sulphonyl hydrazide derivatives produced the corresponding sulphonyl pyrazole derivatives 11a, b, while its reaction with hydroxylamine hydrochloride yielded the isoxazole derivative 12. Treatment of the chalcone 3 with thiourea or guanidine sulfate gave the pyrimidine derivatives 13 and 14 respectively. Furthermore, the pyrane derivatives 15-17 were obtained by cyclization of the chalcone 3 with malononitrile, ethyl cyanoacetate and/or ethyl acetoacetate respectively. In addition, 2-oxopyridine 18 was allowed to react with different alkyl halides to yield the corresponding 2-substituted pyridine derivatives 19-21. Schiff base 23 was obtained by the reaction of carbohydrzide derivative 22 with anisaldehyde. Some of synthesized compounds were evaluated for cytotoxicity activity against HepG2 (liver carcinoma cell line) and MCF-7 (brest carcinoma cell line) using Doxorubicin as a reference drug.