Synthesis and antiinflammatory activity of some 1,2,3- and 1,2,4-triazolepropionic acids

J Med Chem. 1978 Dec;21(12):1254-60. doi: 10.1021/jm00210a015.

Abstract

All possible "nonadjacent" phenyltriazolepropionic acids were synthesized and tested for antiinflammatory activity. Two of the isomers displayed activity approximately equal to phenylbutazone: the 4-phenyl-1,2,3,-triazole-2-propionic acid (7) and its reverse counterpart, 2-phenyl-1,2,3-triazole-4-propionic acid (6). The other five isomers were inactive. Since these seven acids are geometrically congruent and possess similar lipophilic characters, antiinflammatory activity must depend on some property that is a function of how the carbon and nitrogen atoms are arranged in the triazole ring.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemical synthesis*
  • Arthritis, Experimental / physiopathology
  • Male
  • Pleural Effusion / physiopathology
  • Propionates / chemical synthesis*
  • Propionates / pharmacology
  • Rats
  • Structure-Activity Relationship
  • Triazoles / chemical synthesis*
  • Triazoles / pharmacology

Substances

  • Anti-Inflammatory Agents
  • Propionates
  • Triazoles