Synthesis of dopamine transporter selective 3-{2-(diarylmethoxyethylidene)}-8-alkylaryl-8-azabicyclo[3.2.1]octanes

Amy L. Bradley, Sari E Izenwasser, Dean Wade, Shaine Cararas, Mark L. Trudell

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

A series of 3-{2-(diarylmethoxyethylidene)}-8-alkylaryl-8-azabicyclo[3.2.1]octanes was synthesized and the binding affinities of the compounds were determined at the dopamine and serotonin transporters. The 8-phenylpropyl analogues 8a (Ki=4.1 nM) and 8b (Ki=3.7 nM) were the most potent compounds of the series with binding affinities 3 times greater than GBR-12909. In addition, 8a (SERT/DAT=327) was over 300-fold more selective for the dopamine transporter than the serotonin transporter.

Original languageEnglish
Pages (from-to)629-632
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume13
Issue number4
DOIs
StatePublished - Feb 1 2003

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Serotonin Plasma Membrane Transport Proteins
Dopamine Plasma Membrane Transport Proteins
8-azabicyclo(3.2.1)octane
vanoxerine

ASJC Scopus subject areas

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

Cite this

Synthesis of dopamine transporter selective 3-{2-(diarylmethoxyethylidene)}-8-alkylaryl-8-azabicyclo[3.2.1]octanes. / Bradley, Amy L.; Izenwasser, Sari E; Wade, Dean; Cararas, Shaine; Trudell, Mark L.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 13, No. 4, 01.02.2003, p. 629-632.

Research output: Contribution to journalArticle

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