Design, synthesis, and biological evaluation of 1,2,4-triazole bearing 5-substituted biphenyl-2-sulfonamide derivatives as potential antihypertensive candidates

Bioorg Med Chem. 2013 Dec 15;21(24):7742-51. doi: 10.1016/j.bmc.2013.10.017. Epub 2013 Oct 23.

Abstract

A series of novel 1,2,4-triazole bearing 5-substituted biphenyl-2-sulfonamide derivatives were designed and synthesized to develop new angiotensin II subtype 2 (AT2) receptor agonists as novel antihypertensive candidates. It was found that 14f (IC50=0.4 nM) and 15e (IC50=5.0 nM) displayed potent AT2 receptor affinity and selectivity in binding assays. Biological evaluation in vivo suggested that 14f is obviously superior to that of reference drug losartan in RHRs, and meanwhile, 14f has no significant impact on heart rate. The interesting activities of these compounds may make them promising candidates as antihypertensive agents.

Keywords: AT(2) receptor; Agonists; Antihypertensive activity; Biphenyl-2-sulfonamide derivatives; Structure–activity relationships.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antihypertensive Agents / chemical synthesis
  • Antihypertensive Agents / chemistry
  • Antihypertensive Agents / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Design*
  • Female
  • Heart Rate / drug effects
  • Liver / drug effects
  • Liver / metabolism
  • Male
  • Molecular Structure
  • Myometrium / drug effects
  • Myometrium / metabolism
  • Rats
  • Rats, Inbred SHR
  • Receptor, Angiotensin, Type 2 / agonists*
  • Receptor, Angiotensin, Type 2 / metabolism
  • Structure-Activity Relationship
  • Sulfonamides / chemistry*
  • Swine
  • Triazoles / chemical synthesis
  • Triazoles / chemistry
  • Triazoles / pharmacology*

Substances

  • Antihypertensive Agents
  • Receptor, Angiotensin, Type 2
  • Sulfonamides
  • Triazoles
  • 1,2,4-triazole