Elaboration of simplified vinca alkaloids and phomopsin hybrids.
Nine simplified vinca alkaloids and phomospin A hybrids, in which vindoline moiety has been replaced by a simpler scaffold, have been elaborated to evaluate their activity on the inhibition of tubulin polymerization. This article deals with the synthesis of various simplified vinca alkaloids, using a stereoselective coupling of catharantine with reactive aromatic compounds and methanol as well as their subsequent condensation with a large peptide chain mimicking those of phomopsin A. Biological evaluation and molecular modeling studies are also reported.
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Centre de recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France.
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D000432:Methanol / Q000737:chemistry; D009183:Mycotoxins / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013816:Thermodynamics; D014404:Tubulin / Q000737:chemistry / Q000378:metabolism; D050257:Tubulin Modulators / Q000138:chemical synthesis / Q000737:chemistry; D014747:Vinblastine / Q000031:analogs & derivatives* / Q000737:chemistry; D014748:Vinca Alkaloids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D009842:Oligopeptides
D000432:Methanol; D009183:Mycotoxins; D014404:Tubulin; D050257:Tubulin Modulators; D014747:Vinblastine; D014748:Vinca Alkaloids; C009667:vindoline; C035753:phomopsin; D009842:Oligopeptides; C017836:catharanthine