Discovery of N-[(3R,5R)-1-azabicyclo[3.2.1]oct-3-yl]furo[2,3-c]pyridine-5-carboxamide as an agonist of the alpha7 nicotinic acetylcholine receptor: in vitro and in vivo activity

Bioorg Med Chem Lett. 2008 Jun 15;18(12):3611-5. doi: 10.1016/j.bmcl.2008.04.070. Epub 2008 May 1.

Abstract

A novel alpha7 nAChR agonist, N-[(3R,5R)-1-azabicyclo[3.2.1]oct-3-yl]furo[2,3-c]pyridine-5-carboxamide (3a, PHA-709829), has been identified for the potential treatment of cognitive deficits in schizophrenia. The compound shows potent and selective alpha7 in vitro activity, excellent brain penetration, good rat oral bioavailability and robust in vivo efficacy in a rat auditory sensory gating model.

MeSH terms

  • Animals
  • Azabicyclo Compounds / chemical synthesis
  • Azabicyclo Compounds / chemistry
  • Azabicyclo Compounds / pharmacology*
  • Benzamides / pharmacology
  • Blood Proteins / drug effects
  • Bridged Bicyclo Compounds / pharmacology
  • Bridged Bicyclo Compounds, Heterocyclic / pharmacology
  • Dogs
  • Dose-Response Relationship, Drug
  • Humans
  • Mice
  • Microsomes, Liver / drug effects
  • Molecular Conformation
  • Nicotinic Agonists / chemical synthesis
  • Nicotinic Agonists / chemistry
  • Nicotinic Agonists / pharmacology*
  • Pyridines / chemical synthesis
  • Pyridines / chemistry
  • Pyridines / pharmacology*
  • Quinuclidines / pharmacology
  • Rats
  • Receptors, Muscarinic / drug effects
  • Receptors, Nicotinic / drug effects*
  • Stereoisomerism
  • Structure-Activity Relationship
  • alpha7 Nicotinic Acetylcholine Receptor

Substances

  • Azabicyclo Compounds
  • Benzamides
  • Blood Proteins
  • Bridged Bicyclo Compounds
  • Bridged Bicyclo Compounds, Heterocyclic
  • Chrna7 protein, human
  • Chrna7 protein, mouse
  • Chrna7 protein, rat
  • N-(1-azabicyclo(2.2.2)oct-3-yl)furo(2,3-c)pyridine-5-carboxamide
  • N-(1-azabicyclo(3.2.1)oct-3-yl)furo(2,3-c)pyridine-5-carboxamide
  • Nicotinic Agonists
  • PNU-282987
  • Pyridines
  • Quinuclidines
  • Receptors, Muscarinic
  • Receptors, Nicotinic
  • alpha7 Nicotinic Acetylcholine Receptor