Synthesis of dopamine transporter selective 3-[2-(diarylmethoxyethylidene)]-8-alkylaryl-8-azabicyclo[3.2.1]octanes.
Bioorg Med Chem Lett, 2003/2/24;13(4):629-32.
Bradley AL[1], Izenwasser S, Wade D, Cararas S, Trudell ML
Affiliations
PMID: 12639545
Impact factor: 2.94
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 (K(i)=4.1 nM) and 8b (K(i)=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.
MeSH terms
Animals; Bridged Bicyclo Compounds, Heterocyclic; Caudate Nucleus; Dopamine Plasma Membrane Transport Proteins; Membrane Glycoproteins; Membrane Transport Modulators; Membrane Transport Proteins; Nerve Tissue Proteins; Octanes; Protein Binding; Rats; Structure-Activity Relationship
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