SAR STUDIES OF FLUORINE-SUBSTITUTED BENZYLAMINES AND SUBSTITUTED 2-PHENYLETHYLAMINES AS SUBSTATES 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 inactiv ators, a series of fluorine-substituted benzylamines and a series of s ubstituted 2-phenylethylamines were synthesized and tested as substrat es and inactivators of monoamine oxidase B. All of the compounds were substrates. None of the benzylamines was an inactivator, but several o f the phenethylamines were. These results suggest that either stronger electron withdrawing character or additional stabilizing factors are needed to stabilize the hypothesized enzyme adduct.