Discovery of 4,5-diphenyl-1,2,4-triazole derivatives as a novel class of selective antagonists for the human V(1A) receptor

Bioorg Med Chem. 2002 Jun;10(6):1905-12. doi: 10.1016/s0968-0896(02)00009-3.

Abstract

In the search for a novel class of selective antagonists for the human V(1A) receptor, high-throughput screening (HTS) of the Yamanouchi chemical library using CHO cells expressing the cloned human V(1A) (hV(1A)) receptor led to the discovery of 5-(4-biphenyl)-4-(2-methoxyphenyl)-3-methyl-1,2,4-triazole (3) which possessed the novel 4,5-diphenyl-1,2,4-triazole structure. Subsequent structure-activity relationships studies on a series of the 4,5-diphenyl-1,2,4-triazole derivatives related to 3 revealed that the 4,5-diphenyl-1,2,4-triazole structure played an essential role in exerting high affinity for the hV(1A) receptor and that introduction of a basic amine moiety to the methoxy part of the 4-phenyl ring was effective in the improvement of both affinity for the hV(1A) receptor and selectivity versus the hV(2) receptor. Compound 3 and the 2-(morphorino)ethoxy derivative (11b) were shown to be antagonists for the hV(1A) receptor, from their effects on AVP-induced [Ca(2+)](i) response in CHO cells expressing the hV(1A) receptor.

MeSH terms

  • Animals
  • Antidiuretic Hormone Receptor Antagonists*
  • Antihypertensive Agents / chemical synthesis
  • Antihypertensive Agents / chemistry
  • Antihypertensive Agents / pharmacology
  • CHO Cells
  • Calcium Signaling / drug effects
  • Cricetinae
  • Humans
  • Radioligand Assay
  • Receptors, Vasopressin / genetics
  • Receptors, Vasopressin / metabolism
  • Structure-Activity Relationship
  • Substrate Specificity
  • Triazoles / chemistry*
  • Triazoles / isolation & purification
  • Triazoles / metabolism
  • Triazoles / pharmacology*

Substances

  • Antidiuretic Hormone Receptor Antagonists
  • Antihypertensive Agents
  • Receptors, Vasopressin
  • Triazoles