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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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Main Authors: Ariffin, Azhar, Thomas, N.F., Kee, C.H., Awang, K., Takeya, K., Morita, H., Hussain, S.I., Chan, K.M., Weber, J.F.F., Wood, P.J., Threadgill, M.D., Lim, C.G., Ng, S.
Format: Article
Language:English
Published: 2010
Subjects:
QD Chemistry
Online Access:http://eprints.um.edu.my/8086/1/Kee-2010-Challenges_associate.pdf
http://eprints.um.edu.my/8086/
http://pubs.rsc.org/en/content/articlepdf/2010/ob/c0ob00296h
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spelling my.um.eprints.80862019-08-27T06:14:35Z http://eprints.um.edu.my/8086/ Challenges associated with the synthesis of unusual O-Carboxamido Stilbenes by the Heck Protocol: intriguing substituent effects, their toxicological and chemopreventive implications Ariffin, Azhar Thomas, N.F. Kee, C.H. Awang, K. Takeya, K. Morita, H. Hussain, S.I. Chan, K.M. Weber, J.F.F. Wood, P.J. Threadgill, M.D. Lim, C.G. Ng, S. QD Chemistry 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. 2010 Article PeerReviewed application/pdf en http://eprints.um.edu.my/8086/1/Kee-2010-Challenges_associate.pdf Ariffin, Azhar 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 http://pubs.rsc.org/en/content/articlepdf/2010/ob/c0ob00296h 10.1039/c0ob00296h
institution Universiti Malaya
building UM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaya
content_source UM Research Repository
url_provider http://eprints.um.edu.my/
language English
topic QD Chemistry
spellingShingle QD Chemistry
Ariffin, Azhar
Thomas, N.F.
Kee, C.H.
Awang, K.
Takeya, K.
Morita, H.
Hussain, S.I.
Chan, K.M.
Weber, J.F.F.
Wood, P.J.
Threadgill, M.D.
Lim, C.G.
Ng, S.
Challenges associated with the synthesis of unusual O-Carboxamido Stilbenes by the Heck Protocol: intriguing substituent effects, their toxicological and chemopreventive implications
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 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.
format Article
author Ariffin, Azhar
Thomas, N.F.
Kee, C.H.
Awang, K.
Takeya, K.
Morita, H.
Hussain, S.I.
Chan, K.M.
Weber, J.F.F.
Wood, P.J.
Threadgill, M.D.
Lim, C.G.
Ng, S.
author_facet Ariffin, Azhar
Thomas, N.F.
Kee, C.H.
Awang, K.
Takeya, K.
Morita, H.
Hussain, S.I.
Chan, K.M.
Weber, J.F.F.
Wood, P.J.
Threadgill, M.D.
Lim, C.G.
Ng, S.
author_sort Ariffin, Azhar
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
url http://eprints.um.edu.my/8086/1/Kee-2010-Challenges_associate.pdf
http://eprints.um.edu.my/8086/
http://pubs.rsc.org/en/content/articlepdf/2010/ob/c0ob00296h
_version_ 1643688214708355072
score 13.211869

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