Challenges associated with the synthesis of unusual O-Carboxamido Stilbenes by the Heck Protocol: intriguing substituent effects, their toxicological and chemopreventive implications

Ariffin, A. and Thomas, N.F. and Kee, C.H. and Awang, K. and Takeya, K. and Morita, H. and Hussain, S.I. and Chan, K.M. and Weber, J.F.F. and Wood, P.J. and Threadgill, M.D. and Lim, C.G. and Ng, S. (2010) Challenges associated with the synthesis of unusual O-Carboxamido Stilbenes by the Heck Protocol: intriguing substituent effects, their toxicological and chemopreventive implications. Organic & Biomolecular Chemistry, 8 (24). pp. 5646-5660. ISSN 1477-0520

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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 IC50 of 4.9 mu M, 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.

Item Type: Article
Additional Information: Department of Chemistry, Faculty of Science Building, University of Malaya, 50603 Kuala Lumpur, MALAYSIA
Uncontrolled Keywords: Amides/*chemistry; Antineoplastic agents/*chemical synthesis/*pharmacology; Catalysis; Cell line; Cell survival/drug effects; HT29 cells; Humans; Oxidation-reduction; Palladium/chemistry; Stilbenes/*chemical synthesis/*pharmacology; Structure-sctivity relationship
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science > Dept of Chemistry
Depositing User: Miss Malisa Diana
Date Deposited: 03 Jul 2013 04:30
Last Modified: 21 Dec 2014 07:56
URI: http://eprints.um.edu.my/id/eprint/8086

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