Monoamine oxidase-catalyzed oxidation of endo,endo-2-amino-6-[(Z)-2'-phenyl]ethenylbicyclo[2.2.1]heptane, a potential probe for a radical cation intermediate

Xueqing Wang, Richard B. Silverman*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

An 11-step synthesis of endo,endo-2-amino-6-[(E)-2'-phenyl]ethenylbicyclo[2.2.1]heptane (6) and the corresponding (Z)-isomer (7) was carried out in an attempt to make a compound that could trap the purported amine radical cation intermediate during monoamine oxidase (MAO)-catalyzed oxidation of amines. The E-isomer was not a substrate for MAO, and the Z-isomer was a very poor substrate. No trapping product was observed. Possible explanations for the inability of these compounds to trap a potential radical cation intermediate are discussed. Copyright (C) 2000 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)1645-1651
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume8
Issue number7
DOIs
StatePublished - Jul 2000

Funding

We are grateful to the National Institutes of Health (Grant GM32634) for financial support of this research. We thank Charlotte Stern for the crystal structures.

ASJC Scopus subject areas

  • Drug Discovery
  • Molecular Medicine
  • Molecular Biology
  • Biochemistry
  • Clinical Biochemistry
  • Pharmaceutical Science
  • Organic Chemistry

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