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

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.
AuthorsKaoru Warabi, Brian O Patrick, Pamela Austin, Calvin D Roskelley, Michel Roberge, Raymond J Andersen
JournalJournal of natural products (J Nat Prod) Vol. 70 Issue 5 Pg. 736-40 (May 2007) ISSN: 0163-3864 [Print] United States
PMID17407351 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Antineoplastic Agents
  • Diterpenes
  • strongylophorine-26
Topics
  • Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
  • Diterpenes (chemical synthesis, chemistry, pharmacology)
  • Drug Screening Assays, Antitumor
  • Molecular Structure
  • Stereoisomerism
  • Structure-Activity Relationship
  • X-Ray Diffraction

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