Combretastatin a-3 prodrug

Details Combretastatin a-3 prodrug Combretastatin a-3 prodrug

C - Chemistry, Metallurgy

07

F

C07F 9/09 (2006.01) A61K 31/675 (2006.01) A61P 35/00 (2006.01) C07D 213/82 (2006.01) C07D 295/027 (2006.01) C07D 453/02 (2006.01) C07D 453/04 (2006.01) C07F 9/11 (2006.01) C07F 9/12 (2006.01) C07F 9/576 (2006.01)

Patent

CA 2418102

A new and more efficient synthesis of combretastatin A-3 (2a) was completed (8.4% overall yield) starting from methyl gallate and isovanillin with aldehyde 5 and phosphonium salt 8 as key intermediates. Conversion of combretastatin A-3 (2a) to a series of diphosphate prodrugs (lOa -lOl) containing selected anions was achieved. Both the diphosphate sodium (lOa) and potassium salts (lOc) displayed aqueous solubility in excess of 220 mg/ml at room temperature and good cancer cell line inhibitory activity.

L'invention concerne une synthèse de combrétastatine A3 (2a) nouvelle et plus efficace, effectuée (à un rendement global de 8,4%) à partir de gallate de méthyle et d'isovanilline, un aldéhyde (5) et un sel de phosphonium (8) servant d'intermédiaires clés. Ladite synthèse a consisté à transformer la combrétastatine A3 (2a) en un ensemble de promédicaments diphosphates (10a 10l) contenant une sélection d'anions. Aussi bien le sodium de diphosphate (10a) que les sels de potassium (10c) ont présenté une solubilité aqueuse en excès de 220 mg/ml à température ambiante, et une activité inhibitrice des lignées cellulaires cancéreuses satisfaisante.

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