Synthesis and Biological Evaluation of Cyclopentaquinoline Derivatives as Nonsteroidal Glucocorticoid Receptor Antagonists

J Med Chem. 2015 Jun 25;58(12):4918-26. doi: 10.1021/jm501758q. Epub 2015 Jun 4.

Abstract

The steroidal glucocorticoid antagonist mifepristone has been reported to improve the symptoms of depression. We report the discovery of 6-(3,5-dimethylisoxazol-4-yl)-2,2,4,4-tetramethyl-2,3,4,7,8,9-hexahydro-1H-cyclopenta[h]quinolin-3-one 3d (QCA-1093) as a novel nonsteroidal glucocorticoid receptor antagonist. The compound displayed potent in vitro activity, high selectivity over other steroid hormone receptors, and significant antidepressant-like activity in vivo.

MeSH terms

  • Animals
  • Antidepressive Agents / chemical synthesis
  • Antidepressive Agents / chemistry*
  • Antidepressive Agents / pharmacology
  • Antidepressive Agents / therapeutic use*
  • Cell Line
  • Depression / drug therapy*
  • Humans
  • Male
  • Molecular Docking Simulation
  • Quinolines / chemical synthesis
  • Quinolines / chemistry*
  • Quinolines / pharmacology
  • Quinolines / therapeutic use*
  • Rats
  • Rats, Wistar
  • Receptors, Glucocorticoid / antagonists & inhibitors*
  • Receptors, Glucocorticoid / metabolism
  • Structure-Activity Relationship

Substances

  • Antidepressive Agents
  • Quinolines
  • Receptors, Glucocorticoid