Synthesis and evaluation of novel pyrazolo[1,5-alpha]pyrimidine derivatives as nonpeptide angiotensin II receptor antagonists

Chem Pharm Bull (Tokyo). 1995 Jun;43(6):960-5. doi: 10.1248/cpb.43.960.

Abstract

A novel series of 6-alkyl-7-oxo-4,7-dihydropyrazolo[1,5-alpha]pyrimidine-3-carboxyli c acid derivatives was prepared as angiotensin II (AII) receptor antagonists. When evaluated in an in vitro binding assay using COS cells transfected with a cDNA encoding a human AT1 angiotensin II receptor, the compounds in this series showed Ki values in the range of 0.4-4.0 nM. In anesthetized spontaneously hypertensive rats (SHRs), administration of the 6-propyl derivative 4d (1 mg/kg, i.v.) reduced the mean blood pressure (MBP) by a maximum of more than 30 mmHg from the normal value.

MeSH terms

  • Angiotensin II / metabolism*
  • Angiotensin Receptor Antagonists*
  • Animals
  • Antihypertensive Agents / chemical synthesis
  • Antihypertensive Agents / pharmacology
  • Blood Pressure / drug effects
  • Cell Line
  • Chemical Phenomena
  • Chemistry, Physical
  • Humans
  • In Vitro Techniques
  • Kinetics
  • Liver / drug effects
  • Liver / metabolism
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / pharmacology
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / pharmacology
  • Rats
  • Rats, Inbred SHR
  • Receptors, Angiotensin / biosynthesis

Substances

  • Angiotensin Receptor Antagonists
  • Antihypertensive Agents
  • Pyrazoles
  • Pyrimidines
  • Receptors, Angiotensin
  • Angiotensin II