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J Fluor Chem. 2008 Sep;129(9):875-880.

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.

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1
Organisch-Chemisches Institut and International NRW Graduate School of Chemistry, Universität Münster, Corrensstr. 40, D-48149 Münster, Germany.

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.

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