Synthesis and dopamine transporter binding affinities of 3α-benzyl-8-(diarylmethoxyethyl)-8-azabicyclo[3.2.1]octanes

Amy L. Bradley, Sari E Izenwasser, Dean Wade, Cheryl Klein-Stevens, Naijue Zhu, Mark L. Trudell

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

A series of 3α-benzyl-8-(diarylmethoxyethyl)-8-azabicyclo[3.2.1]octanes was synthesized and the binding affinities of the compounds were determined at the dopamine transporter. The unsubstituted analogue 7b (Ki=98 nM) was the most potent compound of the series with binding affinity three-times greater than cocaine and only 5-fold less than GBR-12909. The structure-activity data for 7a-f suggests that these compounds may be binding at the dopamine transporter in a similar fashion to GBR 12909.

Original languageEnglish
Pages (from-to)2387-2390
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume12
Issue number17
DOIs
StatePublished - Sep 2 2002

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

ASJC Scopus subject areas

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

Cite this

Synthesis and dopamine transporter binding affinities of 3α-benzyl-8-(diarylmethoxyethyl)-8-azabicyclo[3.2.1]octanes. / Bradley, Amy L.; Izenwasser, Sari E; Wade, Dean; Klein-Stevens, Cheryl; Zhu, Naijue; Trudell, Mark L.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 12, No. 17, 02.09.2002, p. 2387-2390.

Research output: Contribution to journalArticle

Bradley, Amy L. ; Izenwasser, Sari E ; Wade, Dean ; Klein-Stevens, Cheryl ; Zhu, Naijue ; Trudell, Mark L. / Synthesis and dopamine transporter binding affinities of 3α-benzyl-8-(diarylmethoxyethyl)-8-azabicyclo[3.2.1]octanes. In: Bioorganic and Medicinal Chemistry Letters. 2002 ; Vol. 12, No. 17. pp. 2387-2390.
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