Challenges associated with the synthesis of unusual o-carboxamido stilbenes by the Heck protocol

Intriguing substituent effects, their toxicological and chemopreventive implications

Chin Hui Kee, Azhar Ariffin, Khalijah Awang, Koichi Takeya, Hiroshi Morita, Salmaan Inayat Hussain, Chan Kok Meng, Pauline J. Wood, Michael D. Threadgill, Chuan Gee Lim, Seikweng Ng, Jean Frédéric F Weber, Noel F. Thomas

Research output: Contribution to journalArticle

9 Citations (Scopus)

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 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.

Original languageEnglish
Pages (from-to)5646-5660
Number of pages15
JournalOrganic and Biomolecular Chemistry
Volume8
Issue number24
DOIs
Publication statusPublished - 21 Dec 2010

Fingerprint

Stilbenes
stilbene
Toxicology
Derivatives
synthesis
Cytotoxicity
Colonic Neoplasms
Inhibitory Concentration 50
Hepatocytes
cancer
Cells
resveratrol

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

Cite this

Challenges associated with the synthesis of unusual o-carboxamido stilbenes by the Heck protocol : Intriguing substituent effects, their toxicological and chemopreventive implications. / Kee, Chin Hui; Ariffin, Azhar; Awang, Khalijah; Takeya, Koichi; Morita, Hiroshi; Hussain, Salmaan Inayat; Kok Meng, Chan; Wood, Pauline J.; Threadgill, Michael D.; Lim, Chuan Gee; Ng, Seikweng; Weber, Jean Frédéric F; Thomas, Noel F.

In: Organic and Biomolecular Chemistry, Vol. 8, No. 24, 21.12.2010, p. 5646-5660.

Research output: Contribution to journalArticle

Kee, Chin Hui ; Ariffin, Azhar ; Awang, Khalijah ; Takeya, Koichi ; Morita, Hiroshi ; Hussain, Salmaan Inayat ; Kok Meng, Chan ; Wood, Pauline J. ; Threadgill, Michael D. ; Lim, Chuan Gee ; Ng, Seikweng ; Weber, Jean Frédéric F ; Thomas, Noel F. / Challenges associated with the synthesis of unusual o-carboxamido stilbenes by the Heck protocol : Intriguing substituent effects, their toxicological and chemopreventive implications. In: Organic and Biomolecular Chemistry. 2010 ; Vol. 8, No. 24. pp. 5646-5660.
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