Identification of a novel, selective GABA(A) alpha5 receptor inverse agonist which enhances cognition

J Med Chem. 2003 May 22;46(11):2227-40. doi: 10.1021/jm020582q.

Abstract

In pursuit of a GABA(A) alpha5-subtype-selective inverse agonist to enhance cognition, a series of 6,7-dihydro-2-benzothiophen-4(5H)-ones has been identified as a novel class of GABA(A) receptor ligands. These thiophenes have higher binding affinity for the GABA(A) alpha5 receptor subtype compared to the GABA(A) alpha1, alpha2, and alpha3 subtypes, and several analogues exhibit high GABA(A) alpha5 receptor inverse agonism. 6,6-Dimethyl-3-(2-hydroxyethyl)thio-1-(thiazol-2-yl)-6,7-dihydro-2-benzothiophen-4(5H)-one (43) has been identified as a full inverse agonist at the GABA(A) alpha5 receptor and is functionally selective over the other major GABA(A) receptor subtypes. 43 readily penetrates into the CNS to give selective occupancy of GABA(A) alpha5 receptors. In addition, 43 enhances cognitive performance in rats in the delayed 'matching-to-place' Morris water maze test-a hippocampal-dependent memory task-without the convulsant or proconvulsant activity associated with nonselective, GABA(A) receptor inverse agonists.

MeSH terms

  • Animals
  • Brain / metabolism
  • Cell Line
  • Cognition / drug effects*
  • Female
  • GABA Agonists / adverse effects
  • GABA Agonists / chemical synthesis*
  • GABA Agonists / pharmacology
  • Hippocampus / physiology
  • Humans
  • In Vitro Techniques
  • Ligands
  • Male
  • Maze Learning / drug effects
  • Memory / drug effects
  • Mice
  • Nootropic Agents / adverse effects
  • Nootropic Agents / chemical synthesis*
  • Nootropic Agents / pharmacology
  • Oocytes / drug effects
  • Oocytes / physiology
  • Patch-Clamp Techniques
  • Protein Subunits
  • Radioligand Assay
  • Rats
  • Receptors, GABA-A / drug effects*
  • Seizures / chemically induced
  • Structure-Activity Relationship
  • Thiazoles / adverse effects
  • Thiazoles / chemical synthesis*
  • Thiazoles / pharmacology
  • Thiophenes / adverse effects
  • Thiophenes / chemical synthesis*
  • Thiophenes / pharmacology
  • Xenopus laevis

Substances

  • 6,6-dimethyl-3-(2-hydroxyethyl)thio-1-(thiazol-2-yl)-6,7-dihydro-2-benzothiophen-4(5H)-one
  • GABA Agonists
  • Ligands
  • Nootropic Agents
  • Protein Subunits
  • Receptors, GABA-A
  • Thiazoles
  • Thiophenes