Paper
Selective monoamine oxidase inhibitors. 3. Cyclic compounds related to 4-aminophenethylamine. Preparation and neuron-selective action of some 5-(2-aminoethyl)-2,3-dihydroindoles.
Published Aug 1, 1986 · L. Florvall, Y. Kumar, A. Ask
Journal of medicinal chemistry
13
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Abstract
Nine 5-(2-aminoethyl)-2,3-dihydroindole derivatives were synthesized and tested as monoamine oxidase (MAO) inhibitors in vitro and in vivo. All compounds were found to be selective MAO-A inhibitors in vitro, the most active ones, 5-[1-(2-aminopropyl)]-2,3-dihydro-4-methylindole acetate (3), 5-[1-(2-aminopropyl)]-4-chloro-2,3-dihydroindole acetate (5), 5-[1-(2-aminopropyl)]-2,3-dihydro-1-ethyl-4-methylindole tartrate (6), 5-[1-(2-aminopropyl)]-2,3-dihydro-1-ethyl-6-methylindole tartrate (7), and 5-[1-(2-aminobutyl)]-4-chloro-2,3-dihydroindole acetate (9) being equipotent with amiflamine, (S)-(+)-4-(dimethylamino)-2, alpha-dimethylphenethylamine. Some of the compounds, 3, 6, 5-[1-(2-aminopropyl)]-2,3-dihydroindole acetate (1), and 5-[1-(2-amino-2-methylpropyl)]-2,3-dihydroindole acetate (8), were found to be very potent inhibitors of MAO in serotonergic and/or noradrenergic nerve terminals in the rat brain in vivo, inhibiting MAO within these neurons at doses 1/10 of those required to inhibit MAO in other neurons or cells. Compound 1 was also a potent and selective inhibitor of MAO within dopaminergic nerve terminals in vivo. This neuron selectivity is due to the uptake of these compounds by the neuronal uptake mechanisms.
In Vitro Study5-(2-aminoethyl)-2,3-dihydroindole derivatives are selective monoamine oxidase inhibitors with potential neuron-selective action in serotonergic, noradrenergic, and dopaminergic nerve terminals.
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