title: Synthesis and dopamine transporter binding affinities of 3alpha-benzyl-8-(diarylmethoxyethyl)-8-azabicyclo[3.2.1]octanes.
abstract: A series of 3alpha-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 (K(i)=98nM) 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.
authors.affiliation: Department of Chemistry, University of New Orleans, LA 70148, USA.
authors.forename: Amy L
authors.initials: AL
authors.lastname: Bradley
authors.forename: Sari
authors.initials: S
authors.lastname: Izenwasser
authors.forename: Dean
authors.initials: D
authors.lastname: Wade
authors.forename: Cheryl
authors.initials: C
authors.lastname: Klein-Stevens
authors.forename: Naijue
authors.initials: N
authors.lastname: Zhu
authors.forename: Mark L
authors.initials: ML
authors.lastname: Trudell
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D050483:Dopamine Plasma Membrane Transport Proteins; D018765:Dopamine Uptake Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D008562:Membrane Glycoproteins; D049990:Membrane Transport Modulators; D026901:Membrane Transport Proteins / Q000037:antagonists & inhibitors / Q000378:metabolism*; D009419:Nerve Tissue Proteins; D009795:Octanes / Q000138:chemical synthesis / Q000494:pharmacology; D011485:Protein Binding; D013329:Structure-Activity Relationship
chemical_list: D001643:Bridged Bicyclo Compounds; D050483:Dopamine Plasma Membrane Transport Proteins; D018765:Dopamine Uptake Inhibitors; D008562:Membrane Glycoproteins; D049990:Membrane Transport Modulators; D026901:Membrane Transport Proteins; D009419:Nerve Tissue Proteins; D009795:Octanes