title: Fluorinated phenylcyclopropylamines. Part 6: Effects of electron withdrawing or donating aryl substituents on the inhibition of tyramine oxidase from Arthrobacter sp. by diastereomeric 2-aryl-2-fluoro-cyclopropylamines.
abstract: Diastereomeric arylcyclopropylamines substituted with fluorine in the 2-position and with electron donating or electron withdrawing groups at the aromatic ring were evaluated as inhibitors of microbial tyramine oxidase. The trans-isomers were consistently more potent inhibitors of the enzyme than the cis-isomers. Electron donating substituents increased the potency of tyramine oxidase inhibition, while electron withdrawing substituents decreased the activity. The results obtained are discussed in terms of pK(a) and log D values of the inhibitors as well as the mechanism of action of tranylcypromines and the geometry of the active site of the enzyme.
authors.affiliation: Organisch-Chemisches Institut and International NRW Graduate School of Chemistry, Universität Münster, Corrensstr. 40, D-48149 Münster, Germany.
authors.forename: Svenja
authors.initials: S
authors.lastname: Hruschka
authors.forename: Shinichi
authors.initials: S
authors.lastname: Yoshida
authors.forename: Kenneth L
authors.initials: KL
authors.lastname: Kirk
authors.forename: Günter
authors.initials: G
authors.lastname: Haufe