Development and SAR of functionally selective allosteric modulators of GABAA receptors

Bioorg Med Chem. 2011 May 1;19(9):2927-38. doi: 10.1016/j.bmc.2011.03.035. Epub 2011 Mar 29.

Abstract

Positive modulators at the benzodiazepine site of α2- and α3-containing GABA(A) receptors are believed to be anxiolytic. Through oocyte voltage clamp studies, we have discovered two series of compounds that are positive modulators at α2-/α3-containing GABA(A) receptors and that show no functional activity at α1-containing GABA(A) receptors. We report studies to improve this functional selectivity and ultimately deliver clinical candidates. The functional SAR of cinnolines and quinolines that are positive allosteric modulators of the α2- and α3-containing GABA(A) receptors, while simultaneously neutral antagonists at α1-containing GABA(A) receptors, is described. Such functionally selective modulators of GABA(A) receptors are expected to be useful in the treatment of anxiety and other psychiatric illnesses.

MeSH terms

  • Allosteric Regulation
  • Anti-Anxiety Agents / chemical synthesis
  • Anti-Anxiety Agents / chemistry
  • Anti-Anxiety Agents / pharmacology
  • Benzodiazepines / chemistry
  • GABA-A Receptor Antagonists / chemical synthesis
  • GABA-A Receptor Antagonists / chemistry
  • GABA-A Receptor Antagonists / pharmacology
  • Heterocyclic Compounds, 2-Ring / chemistry
  • Quinolines / chemistry
  • Receptors, GABA-A / chemistry*
  • Receptors, GABA-A / metabolism
  • Structure-Activity Relationship

Substances

  • Anti-Anxiety Agents
  • GABA-A Receptor Antagonists
  • Heterocyclic Compounds, 2-Ring
  • Quinolines
  • Receptors, GABA-A
  • Benzodiazepines
  • quinoline
  • cinnoline