An Efficient Procedure of Synthesis Acyclic C-Glycosides of Thiazolo [4, 5-b]Pyrazine and Imidazo[4,5-d]Thiazole with Expected Anti-Cancer Activities

Abstract

In this research, we aimed to synthesize a new series of C-glycosides that have thiazole-4, 5-diamine base. C-glycosides 8 was prepared by coupling compound 7 with D-glucose in the presence of iodine used as an oxidant/promoter dissolved in acetic acid and stirring at room temperature. Compound 8 was protected by reaction with acetic anhydride in the presence of pyridine gave compound 9. Furthermore, cyclization compound 7 with hydrazine hydrate and D-glucose gave the cyclic glycosides analogs 10. The compound 7 was condensed with phenyl hydrazine hydrochloride and D-xylose gave C-glycoside 11. The anticancer activity of the newly synthesized compounds was tested in vitro for their anticancer activities against human colorectal carcinoma (HCT-116), human prostate adenocarcinoma (PC-3), and human liver hepatocellular carcinoma (HepG-2) cell lines.

Keywords:

• C-glycoside
• D-glucose
• oxidant
• phenyl hydrazine
• thiazole-4,5-diamine and anti-cancer activity

Acknowledgements

A.A. Ghoneim. Thanks Professor Ahmed Fouad El Farargy, Chemistry Department, Faculty of Science, Zagazig University, Zagazig, Egypt for the facilities offered of his effort and abundant facilities in the science of chemistry during the previous stages.

Disclosure statement

The authors declare no conflict of interest, financial or otherwise.