[Vinflunine: a new anti-cancer fluorinated agent derived from Vinca-alkaloids].
Reaction in superacid HF-SbF5 in the presence of CCl4 of vinorelbine yields (4'R)-20',20'difluoro-3',4'dihydrovinorelbine (vinflunine), whereas vinblastine or anhydrovinblastine give the difluoro analog. The reaction implies a 20' chloro derivative as intermediate which undergoes hydrid abstraction at C20' followed by halogen exchange. Vinflunine is presently in phase III experimentation for treatment of bladder cancer and non small lung cancer.
Jacquesy
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UMR 6514 Synthèse et réactivité des substances naturelles, 40, avenue du Recteur Pineau, F 86022 Poitiers, France.
Jouannetaud
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MP
D020533:Angiogenesis Inhibitors / Q000627:therapeutic use*; D000818:Animals; D006801:Humans; D045726:Metalloproteases / Q000037:antagonists & inhibitors / Q000502:physiology; D009369:Neoplasms / Q000188:drug therapy* / Q000473:pathology*; D011480:Protease Inhibitors / Q000494:pharmacology / Q000627:therapeutic use; D040262:Receptors, Vascular Endothelial Growth Factor / Q000037:antagonists & inhibitors
D020533:Angiogenesis Inhibitors; D011480:Protease Inhibitors; D040262:Receptors, Vascular Endothelial Growth Factor; D045726:Metalloproteases