Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 18, Issue 19, Pages 5277-5279Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2008.08.056
Keywords
cancer; garlic; synthesis; ajoene; radical addition
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Funding
- National Research Foundation of South Africa, Atlantic Philanthropies
- Council for Scientific and Industrial Research (CSIR)
- Medical Research Council (MRC)
- University of Cape Town
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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. broblast 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. (c) 2008 Elsevier Ltd. All rights reserved.
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