Challenges associated with the synthesis of unusual o-carboxamido stilbenes by the Heck protocol: Intriguing substituent effects, their toxicological and chemopreventive implications |
| |
Authors: | Kee Chin Hui Ariffin Azhar Awang Khalijah Takeya Koichi Morita Hiroshi Hussain Salmaan Inayat Chan Kok Meng Wood Pauline J Threadgill Michael D Lim Chuan Gee Ng Seikweng Weber Jean Frédéric F Thomas Noel F |
| |
Affiliation: | Department of Chemistry, Faculty of Science, University of Malaya, 50603, Kuala Lumpur, Malaysia. |
| |
Abstract: | The syntheses of fourteen unusual o-carboxamido stilbenes by the Heck protocol revealed surprising complexity related to intriguing substituent effects with mechanistic implications. The unexpected cytotoxic and chemopreventive properties also seem to be substituent dependent. For example, although stilbene 15d (with a 4-methoxy substituent) showed cytotoxicity on HT29 colon cancer cells with an IC(50) of 4.9 μM, the 3,4-dimethoxy derivative (15c) is inactive. It is interesting to observe that the 3,5-dimethoxy derivative (15e) showed remarkable chemopreventive activity in WRL-68 fetal hepatocytes, surpassing the gold standard, resveratrol. The resveratrol concentration needed to be 5 times higher than that of 15e to produce comparable elevation of NQO1. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|