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2-Substituted-3H-indol-3-one-1-oxides: Preparation and Radical Trapping Properties |
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| Authors: | Jeremie Boyer Vania Bernardes-Genisson Vincent Farines Jean-Pierre Souchard Francoise Nepveu |
| Institution: | 1. Laboratoire Pharmacochimie des Substances Naturelles et Pharmacophores Redox, UMR-IRD-UPS 152, Faculté de Pharmacie, Université Paul Sabatier, cedex 4, 31062, Toulouse, Francenepveu@cict.fr;3. Laboratoire Pharmacochimie des Substances Naturelles et Pharmacophores Redox, UMR-IRD-UPS 152, Faculté de Pharmacie, Université Paul Sabatier, cedex 4, 31062, Toulouse, France |
| Abstract: | 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 β-hydrogen atom gives rise to highly stable adducts with free radicals. |
| Keywords: | Indolone-1-oxide Nitrones Free radicals Spin trapping EPR EPR electron paramagnetic resonance -BPN --butylphenylnitrone DMPO 5 5-dimethyl-1pyrroline--oxide HFS hyperfine splitting |