title: Fe(II)-induced reduction of labelled endoperoxides. NMR degradation studies on G3 factor and its methyl ether.
abstract: The behavior of G3 factor and of its methylated or fluorinated analogues G3Me and G3F, was studied under Fe(II) conditions. Degradation products were isolated and characterized in each case. The use of labelled compounds allowed us to propose mechanisms in which a tertiary radical is involved. This radical rearranges by 5-exo-trig cyclization, or disproportionates in the case of G3Me. A correlation between antiplasmodial activity and stability of this radical is proposed.
authors.affiliation: Laboratoire de Synthèse et de Physicochimie de Molécules d'Intérêt Biologique, UMR CNRS 5068, Université Paul Sabatier, 118 Route de Narbonne, F-31062 Toulouse Cedex 04, France. candre@chimie.ups-tlse.fr
authors.forename: Christiane
authors.initials: C
authors.lastname: André-Barrès
authors.forename: Fadia
authors.initials: F
authors.lastname: Najjar
authors.forename: Anne-Lise
authors.initials: AL
authors.lastname: Bottalla
authors.forename: Stéphane
authors.initials: S
authors.lastname: Massou
authors.forename: Chantal
authors.initials: C
authors.lastname: Zedde
authors.forename: Michel
authors.initials: M
authors.lastname: Baltas
authors.forename: Liliane
authors.initials: L
authors.lastname: Gorrichon
mesh_terms: D004987:Ethers / Q000737:chemistry*; D005296:Ferrous Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D010084:Oxidation-Reduction; D010545:Peroxides / Q000737:chemistry*
chemical_list: D004987:Ethers; D005296:Ferrous Compounds; D010545:Peroxides