Acta Pharm. 67 (2017) 495-510

 

full paper

Original research paper

 

Synthesis and cytotoxicity evaluation of thiazole derivatives obtained from 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile

RAFAT M. MOHAREB, AMIRA E. M. ABDALLAH and EBTSAM A. AHMED

amiraelsayed135@ yahoo.com; miroemao@yahoo.com

1 Department of Chemistry, Faculty of Science, Cairo University, Giza, A. R. Egypt

2 Department of Chemistry, Faculty of Science, Helwan University, Ain Helwan
Cairo A. R. Egypt

Accepted October 8, 2017

Published online October 30, 2017

 

Reactivity of 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile towards thioglycolic acid resulted in thiazole derivative 1. The latter reacted with different chemical reagents to give thiazole, pyrano[2,3-d]thiazole and thiazolo[4,5-d]thiazole derivatives. Cytotoxicity effects of the newly synthesized products against six cancer cell lines, namely, human gastric cancer (NUGC), human colon cancer (DLD-1), human liver cancer (HA22T and HEPG-2), human breast cancer (MCF) and nasopharyngeal carcinoma (HONE-1) as well as against a normal fibroblast cell (WI-38) were evaluated. The study showed that the 4,5,6,7 tetrahydrobenzo[b]thiophene derivatives 6a, 7, 8a,b, 9b and 10b,c were the most active compounds. Their potencies were attributed to the presence of the electron withdrawing groups.

 

Keywords: tetrahydrobenzo[b]thiophene, thiazole, pyrano[2,3-d]thiazole, thiazolo[4,5-d]thiazole, cytotoxicity, anticancer activity