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RESEARCH PRODUCT
Synthesis and monoamine uptake inhibition of conformationally constrained 2β-carbomethoxy-3β-phenyl tropanes
René HummerichPatrick J. RissPatrick Schlosssubject
StereochemistryMolecular ConformationLigandsBiochemistryStructure-Activity Relationshipchemistry.chemical_compoundHumansBiogenic MonoaminesPhysical and Theoretical ChemistrySerotonin transporterDopamine transporterSerotonin Plasma Membrane Transport ProteinsDopamine Plasma Membrane Transport ProteinsNorepinephrine Plasma Membrane Transport ProteinsbiologyMonoamine transporterChemistryOrganic ChemistryHEK 293 cellsBiological TransportStereoisomerismTransporterTropaneMonoamine neurotransmitterbiology.proteinSelectivityTropanesdescription
A series of 2beta-carbomethoxy-3beta-phenyl tropanes with conformationally constrained nitrogen substituents were synthesized as potential selective dopamine transporter ligands. These novel compounds were examined for their monoamine uptake inhibition potency at the human dopamine transporter (hDAT), the human serotonin transporter (hSERT) and the human noradrenalin transporter (hNET), stably expressed in human embryonic kidney cells (HEK). A SAR-study was conducted to determine the contribution of extended, 4-fluorinated, conformationally constrained C4 chains at the tropane nitrogen to human monoamine transporter affinity and selectivity.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2009-06-18 | Organic & Biomolecular Chemistry |