title: Elaboration of simplified vinca alkaloids and phomopsin hybrids.
abstract: Nine simplified vinca alkaloids and phomospin A hybrids, in which vindoline moiety has been replaced by a simpler scaffold, have been elaborated to evaluate their activity on the inhibition of tubulin polymerization.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.
authors.affiliation: Centre de recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France.
authors.forename: Quoc Anh
authors.initials: QA
authors.lastname: Ngo
authors.forename: Fanny
authors.initials: F
authors.lastname: Roussi
authors.forename: Sylviane
authors.initials: S
authors.lastname: Thoret
authors.forename: Françoise
authors.initials: F
authors.lastname: Guéritte
mesh_terms: 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
chemical_list: D000432:Methanol; D009183:Mycotoxins; D014404:Tubulin; D050257:Tubulin Modulators; D014747:Vinblastine; D014748:Vinca Alkaloids; C009667:vindoline; C035753:phomopsin; D009842:Oligopeptides; C017836:catharanthine