Synthesis and Anticancer Evaluation of Some New 4-Amino-3-(p-methoxybenzyl)-4,5-dihydro-1,2,4-triazole-5-one Derivatives

BEKİRCAN O., KÜÇÜK M., Kahveci B., Bektas H.

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, vol.63, no.11, pp.1305-1314, 2008 (SCI-Expanded) identifier identifier


4-Amino-3-p-methoxybenzyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl-acetic acid ethyl ester (2) was prepared from 4-amino-4,5-dihydro-1H-1,2,4-triazole-5-one (1) and ethyl bromoacetate. Compound 3 was synthesized by the condensation of 2 with hydrazine hydrate. The treatment of compound 3 with various aromatic aldehydes resulted in the formation of arylidene hydrazides as cistrans conformers 4a-g. Thiosemicarbazide derivative 5 was prepared by the reaction Of compound 3 with phenylisothiocyanate. Cyclization of 5 with sodium hydroxide resulted in the formation of compound 6. Treatment of 6 with benzyl bromide gave compound 7. Four of the newly synthesized compounds were screened for their anticancer activity against a panel of 60 cell lines derived from nine cancer types, namely, non-small cell lung, colon, breast, ovarian, leukemia, renal, melanoma, prostate and CNS cancers at a fixed dose of 10 mu M.