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Strongylophorine-26, an inhibitor of cancer cell invasion: SAR revealed by synthesis of analogues

TitleStrongylophorine-26, an inhibitor of cancer cell invasion: SAR revealed by synthesis of analogues
Publication TypeJournal Article
Year of Publication2007
AuthorsWarabi, K, Patrick, BO, Austin, P, Roskelley, CD, Roberge, M, Andersen, RJ
JournalJournal of Natural Products
Volume70
Pagination736-740
Date PublishedMay
ISBN Number0163-3864
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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