Design, synthesis, and structure-activity relationship of a novel series of GluN2C-selective potentiators

J Med Chem. 2014 Mar 27;57(6):2334-56. doi: 10.1021/jm401695d. Epub 2014 Feb 25.

Abstract

NMDA receptors are tetrameric complexes composed of GluN1 and GluN2A-D subunits that mediate a slow Ca(2+)-permeable component of excitatory synaptic transmission. NMDA receptors have been implicated in a wide range of neurological diseases and thus represent an important therapeutic target. We herein describe a novel series of pyrrolidinones that selectively potentiate only NMDA receptors that contain the GluN2C subunit. The most active analogues tested were over 100-fold selective for recombinant GluN2C-containing receptors over GluN2A/B/D-containing NMDA receptors as well as AMPA and kainate receptors. This series represents the first class of allosteric potentiators that are selective for diheteromeric GluN2C-containing NMDA receptors.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Chromatography, High Pressure Liquid
  • Computational Biology
  • Drug Design
  • Excitatory Amino Acid Agonists / chemical synthesis*
  • Excitatory Amino Acid Agonists / pharmacology*
  • High-Throughput Screening Assays
  • Humans
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Oocytes / drug effects
  • Patch-Clamp Techniques
  • Pyrrolidinones / chemical synthesis
  • Pyrrolidinones / pharmacology
  • Pyruvates / chemical synthesis
  • Pyruvates / pharmacology
  • Receptors, N-Methyl-D-Aspartate / agonists*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Xenopus laevis

Substances

  • Excitatory Amino Acid Agonists
  • Indicators and Reagents
  • NR2C NMDA receptor
  • Pyrrolidinones
  • Pyruvates
  • Receptors, N-Methyl-D-Aspartate