Challenges associated with the synthesis of unusual o-carboxamido stilbenes by the Heck protocol: Intriguing substituent effects, their toxicological and chemopreventive implications

Challenges associated with the synthesis of unusual o-carboxamido stilbenes by the Heck protocol: Intriguing substituent effects, their toxicological and chemopreventive implications

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...

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Published in:Organic and Biomolecular Chemistry
Main Author: Kee C.H.; Ariffin A.; Awang K.; Takeya K.; Morita H.; Hussain S.I.; Chan K.M.; Wood P.J.; Threadgill M.D.; Lim C.G.; Ng S.; Weber J.F.F.; Thomas N.F.
Format: Article
Language:English
Published: 2010
Online Access:https://www.scopus.com/inward/record.uri?eid=2-s2.0-78649499220&doi=10.1039%2fc0ob00296h&partnerID=40&md5=c57a68f526802b0ad013c49bf14088b4
id 2-s2.0-78649499220
spelling 2-s2.0-78649499220
Kee C.H.; Ariffin A.; Awang K.; Takeya K.; Morita H.; Hussain S.I.; Chan K.M.; Wood P.J.; Threadgill M.D.; Lim C.G.; Ng S.; Weber J.F.F.; Thomas N.F.
Challenges associated with the synthesis of unusual o-carboxamido stilbenes by the Heck protocol: Intriguing substituent effects, their toxicological and chemopreventive implications
2010
Organic and Biomolecular Chemistry
8
24
10.1039/c0ob00296h
https://www.scopus.com/inward/record.uri?eid=2-s2.0-78649499220&doi=10.1039%2fc0ob00296h&partnerID=40&md5=c57a68f526802b0ad013c49bf14088b4
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. © 2010 The Royal Society of Chemistry.

14770520
English
Article
All Open Access; Green Open Access
author Kee C.H.; Ariffin A.; Awang K.; Takeya K.; Morita H.; Hussain S.I.; Chan K.M.; Wood P.J.; Threadgill M.D.; Lim C.G.; Ng S.; Weber J.F.F.; Thomas N.F.
spellingShingle Kee C.H.; Ariffin A.; Awang K.; Takeya K.; Morita H.; Hussain S.I.; Chan K.M.; Wood P.J.; Threadgill M.D.; Lim C.G.; Ng S.; Weber J.F.F.; Thomas N.F.
Challenges associated with the synthesis of unusual o-carboxamido stilbenes by the Heck protocol: Intriguing substituent effects, their toxicological and chemopreventive implications
author_facet Kee C.H.; Ariffin A.; Awang K.; Takeya K.; Morita H.; Hussain S.I.; Chan K.M.; Wood P.J.; Threadgill M.D.; Lim C.G.; Ng S.; Weber J.F.F.; Thomas N.F.
author_sort Kee C.H.; Ariffin A.; Awang K.; Takeya K.; Morita H.; Hussain S.I.; Chan K.M.; Wood P.J.; Threadgill M.D.; Lim C.G.; Ng S.; Weber J.F.F.; Thomas N.F.
title Challenges associated with the synthesis of unusual o-carboxamido stilbenes by the Heck protocol: Intriguing substituent effects, their toxicological and chemopreventive implications
title_short Challenges associated with the synthesis of unusual o-carboxamido stilbenes by the Heck protocol: Intriguing substituent effects, their toxicological and chemopreventive implications
title_full Challenges associated with the synthesis of unusual o-carboxamido stilbenes by the Heck protocol: Intriguing substituent effects, their toxicological and chemopreventive implications
title_fullStr Challenges associated with the synthesis of unusual o-carboxamido stilbenes by the Heck protocol: Intriguing substituent effects, their toxicological and chemopreventive implications
title_full_unstemmed Challenges associated with the synthesis of unusual o-carboxamido stilbenes by the Heck protocol: Intriguing substituent effects, their toxicological and chemopreventive implications
title_sort Challenges associated with the synthesis of unusual o-carboxamido stilbenes by the Heck protocol: Intriguing substituent effects, their toxicological and chemopreventive implications
publishDate 2010
container_title Organic and Biomolecular Chemistry
container_volume 8
container_issue 24
doi_str_mv 10.1039/c0ob00296h
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-78649499220&doi=10.1039%2fc0ob00296h&partnerID=40&md5=c57a68f526802b0ad013c49bf14088b4
description 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. © 2010 The Royal Society of Chemistry.
publisher
issn 14770520
language English
format Article
accesstype All Open Access; Green Open Access
record_format scopus
collection Scopus
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