Inhibition of Monoamine oxidases by fluorinated phenylcyclopropylamines
2006
Yoshida, S.(Tottori-ken. Industrial Research Inst. (Japan)) | Haufe, G. | Kirk, K.L.
Fluorinated phenylcyclopropylamines were synthesized to develop novel inhibitors for monoamine oxidases (MAOs) which involved in Parkinson's disease, depressive illnesses and so on. 2-Fluoro-2-phenycyclopropylamine was a good inhibitor against three kinds of MAOS (copper-containing MAO, flavin-containing MAO-A and -B) than a non-fluorinated compound, 2-phenylcyclopropylamine . Introduction of methyl group to the aromatic ring of 2-fluoro-2-phenycyclopropylamine increased the inhibitory against copper-containing MAO, and fluorine and chlorine were effective for MAO-A and -B. Fluorination at the 2-position of 1-phenylcyclopropylamine, which was known as a selective inhibitor of MAO-B relative to MAO-A reversed the selectivity and resulted in a potent inhibitor selective for MAO-A. These results suggest that the stereochemisty of the fluorine substitution at cyclopropane ring and the p-substitution of the aromatic ring have a strong influence on the level and selectivity of inhibition.
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