New analogues of N-(2-aminoethyl)-4-chlorobenzamide (Ro 16-6491). Some of the most potent monoamine oxidase-B inactivators.
A series of halo- and nitro-substituted analogues of N-(2-aminoethyl)benzamide has been synthesized. All of the compounds are competitive, time-dependent inhibitors of monoamine oxidase-B (MAO-B), but upon dialysis complete return of enzyme activity is observed for all compounds. Therefore, these are mechanism-based reversible inhibitors of MAO-B. The relative potencies of the compounds are rationalized in terms of steric and hydrophobic effects.
Annan
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Department of Chemistry, Northwestern University, Evanston, Illinois 60208-3113.
Silverman
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RB
D000818:Animals; D001549:Benzamides / Q000737:chemistry* / Q000494:pharmacology; D001667:Binding, Competitive; D002417:Cattle; D003956:Dialysis; D008099:Liver / Q000201:enzymology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D008995:Monoamine Oxidase / Q000378:metabolism*; D008996:Monoamine Oxidase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship
D001549:Benzamides; D008996:Monoamine Oxidase Inhibitors; C051040:Ro 16-6491; D008995:Monoamine Oxidase