1,3,5-Trisubstituted Pyrazoles as Potent Negative Allosteric Modulators of the mGlu2/3 Receptors

ChemMedChem. 2017 Jun 21;12(12):905-912. doi: 10.1002/cmdc.201700101. Epub 2017 Apr 10.

Abstract

The metabotropic glutamate subtype 2 (mGlu2 ) receptor is a presynaptic membrane receptor distributed widely in brain that provides feedback inhibitory control of glutamate release. Inhibition of the mGlu2 receptor function with a negative allosteric modulator (NAM) enhances activity-dependent glutamate release, which may be of therapeutic benefit for the treatment of neurological and psychiatric disorders. An attractive pyrazole hit was identified after a high-throughput screening (HTS) campaign. The evolution of this hit is described by structure-activity relationship (SAR) studies on specific parts of the molecule. From near micromolar potency we could obtain compounds with single-digit nanomolar activity in the mGlu2 NAM GTPγS assay. In addition to SAR on in vitro potency, a more detailed overview is given with a specific set of compounds on the excellent agreement between in vitro potency, free brain concentration, and ex vivo mGlu2 receptor occupancy. Finally, to obtain improved drug-like compounds, plans for future research are suggested toward increasing free brain concentration while maintaining high in vitro potency.

Keywords: ex vivo occupancy; metabotropic glutamate 2 receptor; negative allosteric modulators; pyrazoles.

MeSH terms

  • Allosteric Regulation / drug effects
  • Animals
  • Cell Line
  • Dose-Response Relationship, Drug
  • HEK293 Cells
  • Humans
  • Microsomes, Liver / chemistry
  • Microsomes, Liver / metabolism
  • Molecular Structure
  • Permeability / drug effects
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology*
  • Rats
  • Receptors, Metabotropic Glutamate / chemistry*
  • Receptors, Metabotropic Glutamate / metabolism*
  • Structure-Activity Relationship

Substances

  • Pyrazoles
  • Receptors, Metabotropic Glutamate
  • metabotropic glutamate receptor 2