title: Evidence for a trianion intermediate in the metalation of 4-hydroxy-6,7-dimethoxy-8-methyl-2-naphthoic acid. Methodology and application to racemic 5,5'-didesisopropyl-5,5'-dialkylapogossypol derivatives.
abstract: The metalation of 4-hydroxy-6,7-dimethoxy-8-methyl-2-naphthoic acid (8) affording trianion 6 is presented and applied to the regioselective efficient construction of a series of 5,5'-didesisopropyl-5,5'-dialkylapogossypol derivatives 3 that are potent pan-active inhibitors of antiapoptotic Bcl-2 family proteins.
authors.affiliation: Université du Maine and CNRS, Unité de Chimie Organique Moléculaire et Macromoléculaire (UMR 6011), Faculté des Sciences, avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France.
authors.forename: Tin Thanh
authors.initials: TT
authors.lastname: Le
authors.forename: Nguyet Trang Thanh
authors.initials: NT
authors.lastname: Chau
authors.forename: Tai Tan
authors.initials: TT
authors.lastname: Nguyen
authors.forename: Josselin
authors.initials: J
authors.lastname: Brien
authors.forename: Trieu Tien
authors.initials: TT
authors.lastname: Thai
authors.forename: Arnaud
authors.initials: A
authors.lastname: Nourry
authors.forename: Anne-Sophie
authors.initials: AS
authors.lastname: Castanet
authors.forename: Kim Phi Phung
authors.initials: KP
authors.lastname: Nguyen
authors.forename: Jacques
authors.initials: J
authors.lastname: Mortier
mesh_terms: D000818:Animals; D000838:Anions / Q000737:chemistry*; D017209:Apoptosis / Q000187:drug effects; D006072:Gossypol / Q000031:analogs & derivatives* / Q000737:chemistry; D018020:Lithium Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008670:Metals / Q000737:chemistry*; D051379:Mice; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D019253:Proto-Oncogene Proteins c-bcl-2 / Q000737:chemistry / Q000187:drug effects; D013237:Stereoisomerism
chemical_list: C557995:4-hydroxy-6,7-dimethoxy-8-methyl-2-naphthoic acid; D000838:Anions; D018020:Lithium Compounds; D008670:Metals; D009281:Naphthalenes; D019253:Proto-Oncogene Proteins c-bcl-2; C492806:apogossypol; D006072:Gossypol