title: 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.
authors.affiliation: Department of Chemistry, University of British Columbia, Vancouver, B.C. V6T 1Z1, Canada.
authors.forename: Kaoru
authors.initials: K
authors.lastname: Warabi
authors.forename: Brian O
authors.initials: BO
authors.lastname: Patrick
authors.forename: Pamela
authors.initials: P
authors.lastname: Austin
authors.forename: Calvin D
authors.initials: CD
authors.lastname: Roskelley
authors.forename: Michel
authors.initials: M
authors.lastname: Roberge
authors.forename: Raymond J
authors.initials: RJ
authors.lastname: Andersen
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014961:X-Ray Diffraction
chemical_list: D000970:Antineoplastic Agents; D004224:Diterpenes; C491871:strongylophorine-26