title: Design and syntheses of putative bioactive taxanes.
abstract: Reduction of 5 alpha-hydroxy-7 beta,9 alpha,10 beta-triacetoxy-4(20), 11(12)-taxadien-13-one 1 with activated zinc in glacial acetic acid led to rearranged products, including compounds with double bonds at C3-C4, C10-C11 or with an epoxide at C11-C12. Molecular modeling studies suggested that addition of a side chain at C-20 or C-5 of the taxanes with a C3-C4 double bond might lead to bioactivity. Semi-syntheses and results of bioactivities are discussed.
authors: Human Health Research Center, INRS-Institut Armand-Frappier, Université du Québec, 531 Boulevard des Prairies, Laval, Québec, Canada H7V 1B7.
authors: Anastasia
authors: A
authors: Nikolakakis
authors: Jian Hui
authors: JH
authors: Wu
authors: Gerald
authors: G
authors: Batist
authors: Françoise
authors: F
authors: Sauriol
authors: Orval
authors: O
authors: Mamer
authors: Lolita O
authors: LO
authors: Zamir
mesh_terms: D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D016339:Spectrometry, Mass, Fast Atom Bombardment; D043823:Taxoids
chemical_list: D001952:Bridged-Ring Compounds; D043823:Taxoids; C080625:taxane