Design and Synthesis of Non-Peptide, Selective Orexin Receptor 2 Agonists

J Med Chem. 2015 Oct 22;58(20):7931-7. doi: 10.1021/acs.jmedchem.5b00988. Epub 2015 Aug 26.

Abstract

Orexins are a family of neuropeptides that regulate sleep/wakefulness, acting on two G-protein-coupled receptors, orexin receptors 1 (OX1R) and 2 (OX2R). Genetic and pharmacologic evidence suggests that orexin receptor agonists, especially OX2R agonist, will be useful for mechanistic therapy of the sleep disorder narcolepsy/cataplexy. We herein report the discovery of a potent (EC50 on OX2R is 0.023 μM) and OX2R-selective (OX1R/OX2R EC50 ratio is 70) agonist, 4'-methoxy-N,N-dimethyl-3'-[N-(3-{[2-(3-methylbenzamido)ethyl]amino}phenyl)sulfamoyl]-(1,1'-biphenyl)-3-carboxamide 26.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Benzamides / chemical synthesis*
  • Benzamides / pharmacology*
  • CHO Cells
  • Calcium / metabolism
  • Cataplexy / drug therapy
  • Cell Line, Tumor
  • Cricetinae
  • Cricetulus
  • Drug Design
  • High-Throughput Screening Assays
  • Humans
  • Hydrogen Bonding
  • Models, Molecular
  • Narcolepsy / drug therapy
  • Orexin Receptors / agonists*
  • Small Molecule Libraries
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / pharmacology*
  • X-Ray Diffraction

Substances

  • 4'-methoxy-N,N-dimethyl-3'-(N-(3-((2-(3-methylbenzamido)ethyl)amino)phenyl)sulfamoyl)-(1,1'-biphenyl)-3-carboxamide
  • Benzamides
  • Orexin Receptors
  • Small Molecule Libraries
  • Sulfonamides
  • Calcium