title: Synthesis of cytotoxic ferrocenyl flavones via a ferricenium-mediated 1,6-oxidative cyclization.
abstract: The oxidation of the ferrocenyl group of 2'-hydroxyferrocenyl chalcones activates the beta-position of the unsaturated ketone to nucleophilic attack to yield the first examples of ferrocenyl flavones. These compounds are significantly more cytotoxic than their organic analogs on B16 melanoma cells, with IC(50) values in the low micromolar range.
authors.affiliation: Chimie ParisTech (Ecole Nationale Supérieure de Chimie de Paris), Laboratoire Charles Friedel, UMR CNRS 7223, 11 rue Pierre et Marie Curie, 75231 Paris cedex 05, France.
authors.forename: Jean-Philippe
authors.initials: JP
authors.lastname: Monserrat
authors.forename: Guy G
authors.initials: GG
authors.lastname: Chabot
authors.forename: Louis
authors.initials: L
authors.lastname: Hamon
authors.forename: Lionel
authors.initials: L
authors.lastname: Quentin
authors.forename: Daniel
authors.initials: D
authors.lastname: Scherman
authors.forename: Gérard
authors.initials: G
authors.lastname: Jaouen
authors.forename: Elizabeth A
authors.initials: EA
authors.lastname: Hillard
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D047188:Chalcones / Q000138:chemical synthesis / Q000737:chemistry / Q000627:therapeutic use; D003500:Cyclization; D005296:Ferrous Compounds / Q000737:chemistry*; D047309:Flavones / Q000737:chemistry* / Q000627:therapeutic use / Q000633:toxicity; D008546:Melanoma, Experimental / Q000188:drug therapy; D000075163:Metallocenes; D051379:Mice; D010084:Oxidation-Reduction
chemical_list: D000970:Antineoplastic Agents; D047188:Chalcones; D005296:Ferrous Compounds; D047309:Flavones; D000075163:Metallocenes; C004998:ferrocene