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Bioorg Med Chem Lett. 2008 Oct 1;18(19):5277-9. doi: 10.1016/j.bmcl.2008.08.056. Epub 2008 Aug 22.

Substituted ajoenes as novel anti-cancer agents.

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Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa.


A new synthesis of the ajoene pharmacophore core is presented involving the regioselective radical addition of a thiyl radical to a terminal alkyne as the key step. The synthesis allows structural variation of the two end groups on sulfur, and a range of novel derivatives varying the R(1) group (sulfoxide end) has been prepared and tested against CT-1 transformed fibroblast cells for anti-cancer activity. The results indicate comparable or even improved activity compared to the parent natural product ajoene isomers. This opens up the way to systematically studying the biology of the ajoene core.

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