Selective inhibitors of monoamine oxidase. 3. Structure-activity relationship of tricyclics bearing imidazoline, oxadiazole, or tetrazole groups.
Inhibition of monoamine oxidase A (MAO A) is believed to cause antidepressant and possibly antianxiety effects.  The previous paper had developed structure-activity relationships (SAR) for in vitro MAO A inhibition by tricyclic N-arylamides.  It is shown in this paper that the same in vitro SAR can be carried over to tricyclics whose potentially toxic amide function is replaced by an appropriately substituted imidazoline, a 1,2,4- or 1,3,4-oxadiazole, or an alkylated tetrazole moiety.  Dialysis of the inhibitor from the enzyme was used as a measure of reversibility which correlates with a low ability to cause a blood pressure rise with ingested tyramine ("cheese effect").
Harfenist
M
M
Division of Organic Chemistry, Wellcome Research Laboratories, Research Triangle Park, North Carolina 27709, USA.
Heuser
D J
DJ
Joyner
C T
CT
Batchelor
J F
JF
White
H L
HL
D007093:Imidazoles / Q000032:analysis*; D008996:Monoamine Oxidase Inhibitors / Q000737:chemistry / Q000494:pharmacology*; D010069:Oxadiazoles / Q000032:analysis*; D013329:Structure-Activity Relationship; D013777:Tetrazoles / Q000032:analysis*
D007093:Imidazoles; D008996:Monoamine Oxidase Inhibitors; D010069:Oxadiazoles; D013777:Tetrazoles