(Acylaryloxy)acetic acid diuretics. 2. (2-Alkyl-2-aryl-1-oxo-5-indanyloxy)acetic acids

J Med Chem. 1978 May;21(5):437-43. doi: 10.1021/jm00203a006.

Abstract

The introduction of an aryl group at the 2 position of the uricosuric diuretics, (1-oxo-2-alkyl-5-indanyloxy)acetic acids, provided compounds with markedly increased potency over their monosubstituted precursors. These compounds were synthesized either by arylation of the corresponding 2-alkyl-5-methoxy-1-indanones with diaryliodonium salts or by alkylation of the 2-aryl-5-methoxy-1-indanones which were cleaved to the corresponding phenols and then converted to the desired oxyacetic acids. Systematic structural variation of the 2-arylindanyloxyacetic acids provided aryl-substituted compounds with varying degrees of uricosuric and diuretic activity.

MeSH terms

  • Acetates / chemical synthesis*
  • Acetates / pharmacology
  • Animals
  • Chlorides / urine
  • Diuretics / chemical synthesis*
  • Dogs
  • Natriuresis / drug effects
  • Pan troglodytes
  • Potassium / urine
  • Rats
  • Stereoisomerism
  • Structure-Activity Relationship
  • Uricosuric Agents / chemical synthesis

Substances

  • Acetates
  • Chlorides
  • Diuretics
  • Uricosuric Agents
  • Potassium