Design and syntheses of putative bioactive taxanes.
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.
Nikolakakis
Anastasia
A
Human Health Research Center, INRS-Institut Armand-Frappier, Université du Québec, 531 Boulevard des Prairies, Laval, Québec, Canada H7V 1B7.
Wu
Jian Hui
JH
Batist
Gerald
G
Sauriol
Françoise
F
Mamer
Orval
O
Zamir
Lolita O
LO
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
D001952:Bridged-Ring Compounds; D043823:Taxoids; C080625:taxane