4-substituted cubylcarbinylamines: a new class of mechanism-based monoamine oxidase B inactivators.
Cubylcarbinylamine (1a), (4-cyclopropylcubyl)carbinylamine (1b), and (4-phenylcubyl)carbinylamine (1c) were synthesized and shown to be time-dependent, irreversible inactivators of monoamine oxidase B (MAO B). Substrate protects the enzyme from inactivation, but beta-mercaptoethanol does not, suggesting that these compounds are mechanism-based inactivators. All three compounds were also substrates for MAO B with partition ratios ranging from 152 to 536. The 4-substituted analogues were more potent inactivators than the unsubstituted analogue, indicating a benefit to 4-substitution in this class of inactivators.
Zhou
J J
JJ
Department of Chemistry, Northwestern University, Evanston, Illinois 60208-3113, USA.
Li
J
J
Upadhyaya
S
S
Eaton
P E
PE
Silverman
R B
RB
D001952:Bridged-Ring Compounds / Q000737:chemistry* / Q000494:pharmacology; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008744:Methylamines / Q000737:chemistry* / Q000494:pharmacology; D008996:Monoamine Oxidase Inhibitors / Q000737:chemistry*; D013379:Substrate Specificity
C105318:(4-cyclopropylcubyl)carbinylamine; C105316:(4-phenylcubyl)carbinylamine; D001952:Bridged-Ring Compounds; D008744:Methylamines; D008996:Monoamine Oxidase Inhibitors; C105317:cubylcarbinylamine