Chemistry and antiinflammatory activities of prodolic-acid and related 1,3,4,9-tetrahydropyrano[3,4-b]indole-1-alkanoic acids. 1

J Med Chem. 1975 Feb;18(2):189-91. doi: 10.1021/jm00236a017.

Abstract

The synthesis and antiinflammatory activities of a series of 23 novel 1,3,4,9-tetrahydropyrano[3,4-b]indole-1-alkanoic acids are described and some relationships between structure and activity are discussed. One of these compounds, 1,3,4,9-tetrahydro-1-propylpyrano[3,4-b]indole-1-acetic acid (prodolic acid, USAN), has been selected for further studies.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemical synthesis*
  • Anti-Inflammatory Agents / therapeutic use
  • Arthritis, Rheumatoid / drug therapy
  • Arthritis, Rheumatoid / immunology
  • Carboxylic Acids / chemical synthesis
  • Carboxylic Acids / therapeutic use
  • Freund's Adjuvant
  • Indoleacetic Acids
  • Indoles / chemical synthesis*
  • Indoles / therapeutic use
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Pyrans / chemical synthesis
  • Pyrans / therapeutic use
  • Rats
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Anti-Inflammatory Agents
  • Carboxylic Acids
  • Indoleacetic Acids
  • Indoles
  • Pyrans
  • Freund's Adjuvant
  • prodolic acid