4-Substituted cubylcarbinylamines: A new class of mechanism-based monoamine oxidase B inactivators

J. J P Zhou, J. Li, S. Upadhyaya, P. E. Eaton, R. B. Silverman

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

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 β-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 mere potent inactivators than the unsubstituted analogue, indicating a benefit to 4-substitution in this class of inactivators.

Original languageEnglish (US)
Pages (from-to)1165-1168
Number of pages4
JournalJournal of Medicinal Chemistry
Volume40
Issue number7
DOIs
StatePublished - 1997

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

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