Synthesis and nicotinic acetylcholine receptor binding affinities of 2- and 3-isoxazolyl-8-azabicyclo[3.2.1]octanes

Jie Cheng, Sari Izenwasser, Chunming Zhang, Suhong Zhang, Dean Wade, Mark L. Trudell

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

A series of epiboxidine homologues, 2- and 3-isoxazole substituted 8-azabicyclo[3.2.1]octane derivatives was synthesized and evaluated as potential ligands for neuronal nicotinic acetylcholine receptors in [ 3H]cytisine labeled rat brain. The 2β-isoxazolyl-8-azabicyclo[3. 2.1]octane 9b (Ki=3 nM) was the most potent compound of the series with a binding affinity twice that of nicotine. The 3β-isoxazolyl-8- azabicyclo[3.2.1]octane 15b (Ki=148 nM) exhibited moderate affinity while the corresponding 2α- and 3α-isomers exhibited micromolar binding affinity.

Original languageEnglish (US)
Pages (from-to)1775-1778
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume14
Issue number7
DOIs
StatePublished - Apr 1 2004

ASJC Scopus subject areas

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

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