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

Background: 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.

Results: 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-7-pyrano[2,3-]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.

Conclusions: Compound has been shown to be useful in the synthesis of a new series of 1,3-thiazole, pyrano[2,3-]thiazole and 4,5-dihydrothiazolo[4,5-]pyridine derivatives using hydrazonoyl halides as precursors. The anticancer efficacy of compounds , , and against MCF-7, a breast cancer cell line, was also compared to the standard anticancer drug doxorubicin.