Send to

Choose Destination
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.

Author information

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


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.

Supplemental Content

Full text links

Icon for PubMed Central
Loading ...
Support Center