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

2013; Royal Society of Chemistry; Volume: 3; Issue: 11 Linguagem: Inglês

10.1039/c2ra22391k

2046-2069

Vivien Stocker, Alina Ghinet, Marie Leman, Benoı̂t Rigo, Régis Millet, Amaury Farce, Déborah Desravines, Joëlle Dubois, Christophe Waterlot, Philippe Gautret,

Click Chemistry and Applications

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.