Synthesis and Antitumor Activity of 1,3,4-Thiadiazole Derivatives Bearing Coumarine Ring

Abstract

In the present study, preparation of a novel series of N'- (3,5-diphenyl-1,3,4-thiadiazol-2(3H)-ylidene)-2-oxo-2H-chromene-3-carbohydrazide (8a-m) was prepared by two methods via the reaction of hydrazonoyl halides with methyl 2-(2oxo-2H-chromene-3-carbonyl)hydrazinecarbodithioate or 3-(5-mercapto-1,3,4oxadiazol-2-yl)-2H-chromen-2-one.Structures of the newly synthesized compounds were elucidated on the basis of elemental analyses and spectral data.All the newly synthesized compounds have been evaluated for their antitumor activity against a liver carcinoma cell line HEPG2-1.Also, their structure activity relationship (SAR) was studied.Many of the tested compounds showed moderate to high anticancer activity with respective to doxorubicin as a reference drug.In continuation of our studies dealing with the utility of hydrazonoyl halides for synthesis of various bridgehead nitrogen polyheterocycles, 1-10 we wish to report herein a new facile synthesis of various functionalized derivatives of 1,3,4-thiadiazoles bearing coumarine moiety that have not been reported hitherto.8][19][20][21] In the light of the above findings and in continuation of authors' efforts to