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

Abstract

6'-Methylpyrido[3,4-b]norhomotropane [synthesis as the racemate reported here] is more potent at the alpha4beta2 nicotinic receptor than any previous bridged nicotinoid. The two nitrogens and 6'-methyl substituent are superimposable on the two nitrogens and 6-chloro substituent of epibatidine, with the best fit on comparing the chair conformer of the (1R)-pyridonorhomotropane with natural (1R)-epibatidine. In this pharmacophore model, the 6'-methyl substituent may be equivalent to the acetyl methyl of acetylcholine.

Knowledge Graph

Similar Paper

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
Synthesis, nicotinic acetylcholine receptor binding, in vitro and in vivo pharmacology properties of 3′-(substituted pyridinyl)-deschloroepibatidine analogs
Bioorganic & Medicinal Chemistry 2015.0
Synthesis and Pharmacological Characterization of Nicotinic Acetylcholine Receptor Properties of (+)- and (−)-Pyrido-[3,4-b]homotropanes
Journal of Medicinal Chemistry 2006.0
Synthesis and Nicotinic Acetylcholine Receptor Binding Properties of Bridged and Fused Ring Analogues of Epibatidine
Journal of Medicinal Chemistry 2007.0
Synthesis and biological characterization of pyridohomotropanes. Structure-activity relationships of conformationally restricted nicotinoids
Journal of Medicinal Chemistry 1988.0
Structure–activity relationships of N-substituted ligands for the α7 nicotinic acetylcholine receptor
Bioorganic & Medicinal Chemistry Letters 2010.0
Synthesis and nicotinic receptor activity of a hydroxylated tropane
Bioorganic & Medicinal Chemistry Letters 2004.0
3-(4-Aminobutyn-1-yl)pyridines: binding at α4β2 nicotinic cholinergic receptors
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 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