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Fluorinated Phenylcyclopropylamines as Inhibitors of Monoamine Oxidases
Author(s) -
Rosen Thomas C.,
Yoshida Shinichi,
Kirk Kenneth L.,
Haufe Günter
Publication year - 2004
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200400053
Subject(s) - tranylcypromine , monoamine oxidase , chemistry , cyclopropane , substituent , tyramine , stereochemistry , monoamine neurotransmitter , ring (chemistry) , regioselectivity , monoamine oxidase b , fluorine , enzyme , biochemistry , organic chemistry , serotonin , catalysis , receptor
Location makes a difference . Fluorinated analogues of the antidepressive tranylcypromine (see structures) are much stronger inhibitors of different monoamine oxidases such as microbial tyramine oxidase or human liver mitochondrial‐outer‐membrane monoamine oxidases A and B. Regiochemistry, as well as relative and absolute stereochemistry of the fluorine substituent at the cyclopropane ring, has a strong influence on the effectiveness of inhibition and on the physicochemical data, such as p K a values, permeability, and log D values.