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Issue 11, 2013
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On the synthesis and biological properties of isocombretastatins: a case of ketone homologation during Wittig reaction attempts

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Abstract

New isocombretastatins were synthesized by reacting the corresponding phenstatin analogs with CH3PPh3Br in presence of tBuOK. These new derivatives showed significant activities against cellular proliferation and tubulin polymerization. In particular, monomethoxylated derivatives of phenstatin and isoCA-4 exhibit similar activities to those of parent phenstatin. Attempts of the Wittig reaction on 2- (or 4-) methoxy-4′-nitrobenzophenones in the same conditions do not lead to the expected isocombretastatins but to methyleneketones with the exclusion of triphenylphosphine. A mechanism for this new ketone homologation was proposed.

Graphical abstract: On the synthesis and biological properties of isocombretastatins: a case of ketone homologation during Wittig reaction attempts

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Article information


Submitted
03 Oct 2012
Accepted
02 Jan 2013
First published
04 Jan 2013

RSC Adv., 2013,3, 3683-3696
Article type
Paper

On the synthesis and biological properties of isocombretastatins: a case of ketone homologation during Wittig reaction attempts

V. Stocker, A. Ghinet, M. Leman, B. Rigo, R. Millet, A. Farce, D. Desravines, J. Dubois, C. Waterlot and P. Gautret, RSC Adv., 2013, 3, 3683
DOI: 10.1039/C2RA22391K

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