A novel class of positive allosteric modulators of AMPA receptors: design, synthesis, and structure-activity relationships of 3-biphenyl-4-yl-4-cyano-5-ethyl-1-methyl-1H-pyrrole-2-carboxylic acid, LY2059346

Bioorg Med Chem Lett. 2006 Oct 1;16(19):5203-6. doi: 10.1016/j.bmcl.2006.07.012. Epub 2006 Jul 25.

Abstract

The synthesis and structure-activity relationship (SAR) of novel and highly potent positive allosteric modulators of AMPA receptors, 3-biphenyl-4-yl-4-cyano-5-ethyl-1-methyl-1H-pyrrole-2-carboxylic acid, are described. These studies indicated that higher potency was achieved with ortho substitution of the distal (D) phenyl of the 3-biphenyl ring and resulted in the discovery of a potent pyrrole LY2059346 (23q), that was selected for further evaluation in in vitro native tissue assays and in vivo experiments.

MeSH terms

  • Allosteric Regulation*
  • Carboxylic Acids / chemical synthesis
  • Carboxylic Acids / pharmacology
  • Cell Line
  • Drug Design
  • Excitatory Amino Acids / metabolism
  • Glutamic Acid / metabolism
  • Humans
  • Pyrroles / chemical synthesis*
  • Pyrroles / pharmacology*
  • Receptors, AMPA / agonists*
  • Structure-Activity Relationship
  • Transfection

Substances

  • Carboxylic Acids
  • Excitatory Amino Acids
  • Pyrroles
  • Receptors, AMPA
  • Glutamic Acid