Discovery and Characterization of 1H-Pyrazol-5-yl-2-phenylacetamides as Novel, Non-Urea-Containing GIRK1/2 Potassium Channel Activators

ACS Chem Neurosci. 2017 Sep 20;8(9):1873-1879. doi: 10.1021/acschemneuro.7b00217. Epub 2017 Jul 19.

Abstract

The G protein-gated inwardly-rectifying potassium channels (GIRK, Kir3) are a family of inward-rectifying potassium channels, and there is significant evidence supporting the roles of GIRKs in a number of physiological processes and as potential targets for numerous indications. Previously reported urea containing molecules as GIRK1/2 preferring activators have had significant pharmacokinetic (PK) liabilities. Here we report a novel series of 1H-pyrazolo-5-yl-2-phenylacetamides in an effort to improve upon the PK properties. This series of compounds display nanomolar potency as GIRK1/2 activators with improved brain distribution (rodent Kp > 0.6).

Keywords: GIRK; Kir3; activator; pharmacokinetics; thallium flux.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Acetamides / pharmacokinetics*
  • Acetamides / pharmacology*
  • Animals
  • Brain / drug effects
  • Brain / metabolism
  • G Protein-Coupled Inwardly-Rectifying Potassium Channels / metabolism*
  • HEK293 Cells
  • Humans
  • Liver / drug effects
  • Liver / metabolism
  • Membrane Transport Modulators / pharmacokinetics*
  • Membrane Transport Modulators / pharmacology*
  • Mice
  • Microsomes, Liver / drug effects
  • Microsomes, Liver / metabolism
  • Molecular Structure
  • Pyrazoles / pharmacokinetics*
  • Pyrazoles / pharmacology*
  • Structure-Activity Relationship

Substances

  • Acetamides
  • G Protein-Coupled Inwardly-Rectifying Potassium Channels
  • Membrane Transport Modulators
  • Pyrazoles