Synthesis of novel thiazole, pyranothiazole, thiazolo[4,5-b ]pyridines and thiazolo[5',4':5,6]pyrano[2,3-d ]pyrimidine derivatives and incorporating isoindoline-1,3-dione group

BMC Chemistry
Mona A HosnyAbdou O Abdelhamid

Abstract

Thiazole is a core structural motif presents in a wide range of natural products. Thiazole derivatives also have a wide range of medicinal and biological properties. The reaction of hydrazonoyl halides with 2-(1-(4-(1,3-dioxoisoindolin-2-yl)phenyl)ethylidene)hydrazinecarbothioamidein ethanol and triethylamine yielded 2-(4-(1-(2-(4-(2-Arylhydrazono)-5-s-4,5-dihydrothiazol-2-yl)hydrazono)-ethyl)phenyl)isoindoline-1,3-dione and 2-(4-(1-(2-(5-(2-Arylhydrazono)-4-oxo-4,5-dihydrothiazol-2-yl)hydrazono)ethyl)-phenyl)isoindoline-1,3-dione.The reaction of 2-(4-(1-(2-(4-oxo-4,5-dihydrothiazol-2-yl)hydrazono)ethyl)phenyl)isoindoline-1,3-dione with arylidenemalononitrile also yielded 5-amino-2-(2-(1-(4-(1,3-dioxoisoindolin-2-yl)phenyl)ethylidene)hydrazinyl)-7-substituted-7H-pyrano[2,3-d]thiazole-6-carbonitrile. The structures of the newly synthesized compound were elucidated whenever possible on the basis of elemental analysis, spectral data, and alternative synthetic routes. Three of them were evaluated against a breast cancer cell line for their antitumor activity. Compound (1) has been shown to be useful in the synthesis of a new series of 1,3-thiazole, pyrano[2,3-d]thiazole and 4,5-dihydrothiazolo[4,5-b]pyridine derivatives using hydra...Continue Reading

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