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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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| Authors: | Svenja Hruschka Kenneth L Kirk |
| Institution: | a Organisch-Chemisches Institut and International NRW Graduate School of Chemistry, Universität Münster, Corrensstr. 40, D-48149 Münster, Germany b Tottori Institute of Industrial Technology, Tottori 689-1112, Japan c Laboratory of Bioorganic Chemistry, National Institute of Diabetes, and Digestive and Kidney Diseases, National Institutes of Health, Department of Health and Human Services, Bethesda, MD 20892, USA |
| 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 pKa 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. |
| Keywords: | Cyclopropylamines Fluorine Monoamine oxidase inhibitors Microbial tyramine oxidase Arthrobacter sp |
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