Structure-activity relationships of N-substituted ligands for the alpha7 nicotinic acetylcholine receptor

Bioorg Med Chem Lett. 2010 Jan 1;20(1):104-7. doi: 10.1016/j.bmcl.2009.11.023. Epub 2009 Nov 14.

Abstract

A series of alpha7 neuronal nicotinic acetylcholine receptor ligands were designed based on a structural combination of a potent, but non-selective ligand, epibatidine, with a selective lead structure, 2. Three series of compounds in which aryl moieties were attached via a linker to different positions on the core structure were studied. A potent and functionally efficacious analog, (3aR,6aS)-2-(6-phenylpyridazin-3-yl)-5-(pyridin-3-ylmethyl)octahydropyrrolo[3,4-c]pyrrole (3a), was identified.

MeSH terms

  • Animals
  • Humans
  • Ligands*
  • Nicotinic Agonists / chemical synthesis
  • Nicotinic Agonists / chemistry*
  • Nicotinic Agonists / pharmacology
  • Oocytes / metabolism
  • Pyridazines / chemical synthesis
  • Pyridazines / chemistry*
  • Pyridazines / pharmacology
  • Pyrroles / chemical synthesis
  • Pyrroles / chemistry*
  • Pyrroles / pharmacology
  • Receptors, Nicotinic / chemistry*
  • Receptors, Nicotinic / metabolism
  • Structure-Activity Relationship
  • Xenopus
  • alpha7 Nicotinic Acetylcholine Receptor

Substances

  • 2-(6-phenylpyridazin-3-yl)-5-(pyridin-3-ylmethyl)octahydropyrrolo(3,4-c)pyrrole
  • Chrna7 protein, human
  • Ligands
  • Nicotinic Agonists
  • Pyridazines
  • Pyrroles
  • Receptors, Nicotinic
  • alpha7 Nicotinic Acetylcholine Receptor