Strongylophorine-26, an inhibitor of cancer cell Invasion: SAR revealed by synthesis of analogues |
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Authors: | Warabi Kaoru Patrick Brian O Austin Pamela Roskelley Calvin D Roberge Michel Andersen Raymond J |
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Institution: | Department of Chemistry, University of British Columbia, Vancouver, B.C. V6T 1Z1, Canada. |
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Abstract: | The absolute configuration of strongylophorine-26 (1) was determined to be 4S, 5R, 8R, 9S, 10S, 13S, 14S by single-crystal X-ray diffraction analysis of the derivative 7 prepared from the co-occurring metabolite strongylophorine-8 (4) and chemical interconversion to the bislactone 8. Synthetic analogues (+)- and (-)-3 have been prepared in order to explore the structure-activity relationship for the anti-invasion pharmacophore of stronglylophorine-26. These studies revealed the unanticipated importance of the A ring lactone moiety for the anti-invasion activity of 1. |
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