4,5-diphenyltriazol-3-ones: openers of large-conductance Ca(2+)-activated potassium (maxi-K) channels

J Med Chem. 2002 Jul 4;45(14):2942-52. doi: 10.1021/jm010569q.

Abstract

A series of diphenyl-substituted heterocycles were synthesized and evaluated by electrophysiological techniques as openers of the cloned mammalian large-conductance, Ca(2+)-activated potassium (maxi-K) channel. The series was designed from deannulation of known benzimidazolone maxi-K opener NS-004 (2) thereby providing an effective template for obtaining structure-activity-related information. The triazolone ring system was the most studied wherein 4,5-diphenyltriazol-3-one 6d (maxi-K = 158%) was identified as the optimal maxi-K channel opener.

MeSH terms

  • Animals
  • Crystallography, X-Ray
  • In Vitro Techniques
  • Large-Conductance Calcium-Activated Potassium Channels
  • Models, Molecular
  • Molecular Conformation
  • Oocytes / drug effects
  • Oocytes / physiology
  • Patch-Clamp Techniques
  • Potassium Channels, Calcium-Activated / agonists*
  • Potassium Channels, Calcium-Activated / physiology
  • Structure-Activity Relationship
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry
  • Triazoles / pharmacology
  • Xenopus laevis

Substances

  • 4-(5-chloro-2-hydroxyphenyl)-5-(3,5-bis(trifluoromethyl)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one
  • Large-Conductance Calcium-Activated Potassium Channels
  • Potassium Channels, Calcium-Activated
  • Triazoles