2-substituted-3H-indol-3-one-1-oxides: preparation and radical trapping properties.
A series of 2-alkyl and 2-aryl substituted-3H-indol-3-one-1-oxides was prepared and evaluated for its radical trapping properties. Spin trapping and electron paramagnetic resonance experiments demonstrate the ability of these indolone-1-oxides to trap hetero- and carbon-centered radicals. The most stable spin adducts (lifetime of several hours) are obtained with 2-alkyl substituted nitrones, the 2-ethyl-5,6-dioxolo-3H-indolone-1-oxide, 5e and the 2-secbutyl-3H-indolone-1-oxide, 5f. These two nitrones are also sensitive to redox reactions in solution. Therefore this indolone-1-oxide series lacking a beta-hydrogen atom gives rise to highly stable adducts with free radicals.
Laboratoire Pharmacochimie des Substances Naturelles et Pharmacophores Redox, UMR-IRD-UPS 152, Faculté de Pharmacie, Université Paul Sabatier, 31062 Toulouse 4, France.
Jeremie
J
Boyer
Vania
V
Bernardes-Genisson
Vincent
V
Farines
Jean-Pierre
JP
Souchard
Francoise
F
Nepveu
D003497:Cyclic N-Oxides / Q000138:chemical synthesis / Q000737:chemistry; D004578:Electron Spin Resonance Spectroscopy / Q000379:methods*; D017665:Hydroxyl Radical; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009589:Nitrogen Oxides; D013113:Spin Labels / Q000138:chemical synthesis*; D019097:Spin Trapping; D013329:Structure-Activity Relationship; D013481:Superoxides / Q000378:metabolism*
D003497:Cyclic N-Oxides; D007211:Indoles; D009589:Nitrogen Oxides; D013113:Spin Labels; C015388:nitrones; D013481:Superoxides; D017665:Hydroxyl Radical