Fe(II)-induced reduction of labelled endoperoxides. NMR degradation studies on G3 factor and its methyl ether.
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.
André-Barrès
Christiane
C
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
Najjar
Fadia
F
Bottalla
Anne-Lise
AL
Massou
Stéphane
S
Zedde
Chantal
C
Baltas
Michel
M
Gorrichon
Liliane
L
D004987:Ethers / Q000737:chemistry*; D005296:Ferrous Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D010084:Oxidation-Reduction; D010545:Peroxides / Q000737:chemistry*
D004987:Ethers; D005296:Ferrous Compounds; D010545:Peroxides