Renal vasodilators. The role of the 4-substituent in isoquinolin-3-ol cardiovascular agents: 4-ureido derivatives of isoquinolin-3-ol with selective renal vasodilator properties

J Med Chem. 1989 May;32(5):990-7. doi: 10.1021/jm00125a011.

Abstract

The synthesis and cardiovascular evaluation of a series of isoquinolin-3-ol derivatives bearing a variety of nitrogen substituents (amino, acylamino, carbamate, and ureido) at C-4 are described. Certain of these compounds have a selective renal vasodilating profile and have minimal effects on arterial blood pressure or heart rate when administered intravenously in the instrumented anesthetized dog. The most potent renal vasodilator in the series is 4-(allylureido)-6,7-dimethoxyisoquinolin-3-ol (38), which at a dose of 1.2 mg/kg iv produces a 97% maximal increase in renal blood flow without significant hypotensive or chronotropic effects. Structure-activity observations on the nature of the 4-substituent and the alkoxy substitution pattern in the aromatic ring of the isoquinolinol nucleus are discussed.

MeSH terms

  • Animals
  • Blood Pressure / drug effects
  • Dogs
  • Heart Rate / drug effects
  • Isoquinolines / pharmacology*
  • Renal Circulation / drug effects*
  • Structure-Activity Relationship
  • Vascular Resistance / drug effects
  • Vasodilator Agents / chemical synthesis
  • Vasodilator Agents / pharmacology*

Substances

  • Isoquinolines
  • Vasodilator Agents
  • isoquinoline