Structure-Activity Relationship Studies in a Series of 2-Aryloxy- N-(pyrimidin-5-yl)acetamide Inhibitors of SLACK Potassium Channels

Molecules. 2024 Nov 21;29(23):5494. doi: 10.3390/molecules29235494.

Abstract

Epilepsy of infancy with migrating focal seizures (EIMFS) is a rare, serious, and pharmacoresistant epileptic disorder often linked to gain-of-function mutations in the KCNT1 gene. KCNT1 encodes the sodium-activated potassium channel known as SLACK, making small molecule inhibitors of SLACK channels a compelling approach to the treatment of EIMFS and other epilepsies associated with KCNT1 mutations. In this manuscript, we describe a hit optimization effort executed within a series of 2-aryloxy-N-(pyrimidin-5-yl)acetamides that were identified via a high-throughput screen. We systematically prepared analogs in four distinct regions of the scaffold and evaluated their functional activity in a whole-cell, automated patch clamp (APC) assay to establish structure-activity relationships for wild-type (WT) SLACK inhibition. Two selected analogs were also profiled for selectivity versus other members of the Slo family of potassium channels, of which SLACK is a member, and versus a panel of structurally diverse ion channels. The same two analogs were evaluated for activity versus the WT mouse channel as well as two clinically relevant mutant human channels.

Keywords: CNS; EIMFS; KCNT1; KNa1.1; MMPSI; SLACK; Slo2.2; epilepsy; pyrimidine.

MeSH terms

  • Acetamides* / chemistry
  • Acetamides* / pharmacology
  • Animals
  • Humans
  • Mice
  • Nerve Tissue Proteins / antagonists & inhibitors
  • Nerve Tissue Proteins / genetics
  • Nerve Tissue Proteins / metabolism
  • Patch-Clamp Techniques
  • Potassium Channel Blockers* / chemistry
  • Potassium Channel Blockers* / pharmacology
  • Potassium Channels, Sodium-Activated
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacology
  • Structure-Activity Relationship

Substances

  • Acetamides
  • Potassium Channel Blockers
  • Potassium Channels, Sodium-Activated
  • KCNT1 protein, human
  • Pyrimidines
  • Nerve Tissue Proteins