SAR studies of fluorine-substituted benzylamines and substituted 2-phenylethylamines as substrates and inactivators of monoamine oxidase B.
To test whether addition of electron-withdrawing substituents to good substrates of monoamine oxidase (MAO) will transform them into inactivators, a series of fluorine-substituted benzylamines and a series of substituted 2-phenylethylamines were synthesized and tested as substrates and inactivators of monoamine oxidase B. All of the compounds were substrates. None of the benzylamines was an inactivator, but several of the phenethylamines were. These results suggest that either stronger electron withdrawing character or additional stabilizing factors are needed to stabilize the hypothesized enzyme adduct.
Silverman
R B
RB
Department of Chemistry, Northwestern University, Evanston, Illinois 60208-3113, USA.
Hawe
W P
WP
D000818:Animals; D001596:Benzylamines / Q000138:chemical synthesis / Q000494:pharmacology*; D002417:Cattle; D004583:Electrons; D017611:Fluorine Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D008099:Liver / Q000201:enzymology; D009682:Magnetic Resonance Spectroscopy; D008995:Monoamine Oxidase / Q000378:metabolism*; D008996:Monoamine Oxidase Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology*; D010627:Phenethylamines / Q000138:chemical synthesis / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013379:Substrate Specificity
D001596:Benzylamines; D017611:Fluorine Compounds; D008996:Monoamine Oxidase Inhibitors; D010627:Phenethylamines; D008995:Monoamine Oxidase