Synthesis of cytotoxic ferrocenyl flavones via a ferricenium-mediated 1,6-oxidative cyclization.
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.
Monserrat
Jean-Philippe
JP
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.
Chabot
Guy G
GG
Hamon
Louis
L
Quentin
Lionel
L
Scherman
Daniel
D
Jaouen
Gérard
G
Hillard
Elizabeth A
EA
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
D000970:Antineoplastic Agents; D047188:Chalcones; D005296:Ferrous Compounds; D047309:Flavones; D000075163:Metallocenes; C004998:ferrocene