Synthesis and nicotinic receptor activity of a hydroxylated tropane

Bioorganic & Medicinal Chemistry Letters
2004.0

Abstract

(+/-)-3alpha-hydroxy homoepibatidine 4 has been synthesized from the alkaloid scopolamine 5 and its properties as a nicotinic agonist assessed. While still binding strongly, the compound showed reduced agonist potency for the alpha(4)beta(2) nAChR compared with the parent compound epibatidine 1. Compound 4 also displayed generally similar binding and selectivity profiles at alpha(4)beta(2), alpha(2)beta(4), alpha(3)beta(4), and alpha(4)beta(4) nAChR subtypes to those for nicotine.

Knowledge Graph

Similar Paper

Synthesis and nicotinic receptor activity of a hydroxylated tropane
Bioorganic & Medicinal Chemistry Letters 2004.0
Epibatidine analogues as selective ligands for the αxβ2-containing subtypes of nicotinic acetylcholine receptors
Bioorganic & Medicinal Chemistry Letters 2005.0
Epibatidine structure–activity relationships
Bioorganic & Medicinal Chemistry Letters 2004.0
Synthesis and pharmacological characterization of bivalent ligands of epibatidine at neuronal nicotinic acetylcholine receptors
Bioorganic & Medicinal Chemistry Letters 2004.0
Synthesis, Nicotinic Acetylcholine Receptor Binding, and Antinociceptive Properties of 3‘-Substituted Deschloroepibatidine Analogues. Novel Nicotinic Antagonists
Journal of Medicinal Chemistry 2005.0
Synthesis and binding affinity at α4β2 and α7 nicotinic acetylcholine receptors of new analogs of epibatidine and epiboxidine containing the 7-azabicyclo[2.2.1]hept-2-ene ring system
Bioorganic & Medicinal Chemistry Letters 2012.0
6′-Methylpyrido[3,4-b]norhomotropane: synthesis and outstanding potency in relation to the α4β2 nicotinic receptor pharmacophore model
Bioorganic & Medicinal Chemistry Letters 2005.0
Epibatidine isomers and analogues: Structure–activity relationships
Bioorganic & Medicinal Chemistry Letters 2006.0
Synthesis, Nicotinic Acetylcholine Receptor Binding, and Antinociceptive Properties of 3′-(Substituted Phenyl)epibatidine Analogues. Nicotinic Partial Agonists
Journal of Natural Products 2010.0
Novel α3β4 Nicotinic Acetylcholine Receptor-Selective Ligands. Discovery, Structure−Activity Studies, and Pharmacological Evaluation
Journal of Medicinal Chemistry 2010.0