Synthesis of 5,6-dichloroindan-1-acids and their tetrazolyl derivatives as analgesic and anti-inflammatory agents

Med Chem. 2012 Sep;8(5):874-82. doi: 10.2174/157340612802084234.

Abstract

Indan derivatives, namely, 5-(5',6'-dichloroindan-1'-yl)-tetrazole (12a) and 5-(5',6'-dichloroindan-1'-yl)- methyltetrazole (12b), were synthesized conveniently from 5,6-dichloroindan-1-carboxylic acid (9a) and 5,6- dichloroindan-1-acetic acid (9b), respectively, as potential analgesic and anti-inflammatory agents. The analgesic and anti-inflammatory properties of 9a, 9b, 12a and 12b were evaluated by the acetic acid induced writhing in Swiss albino mice and the carrageenan-induced rat paw edema models, respectively. Compounds 9a and 12a exhibited significant analgesic activity with the doses of 50 and 100 mg/kg body weight, comparable to that of the positive controls, phenylbutazone, indomethacin and aminopyrine. The anti-inflammatory potencies of 9a and 12a were also comparable to that of the positive control, phenylbutazone. Compounds 9b and 12b showed analgesic and anti-inflammatory activities, but were weaker than that of compounds 9a and 12a.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetic Acid
  • Aminopyrine / pharmacology
  • Analgesics / chemical synthesis*
  • Analgesics / pharmacology
  • Animals
  • Anti-Inflammatory Agents / chemical synthesis*
  • Anti-Inflammatory Agents / pharmacology
  • Carrageenan
  • Dose-Response Relationship, Drug
  • Edema / chemically induced
  • Edema / drug therapy*
  • Indans / chemical synthesis*
  • Indans / pharmacology
  • Indomethacin / pharmacology
  • Mice
  • Pain / chemically induced
  • Pain / drug therapy*
  • Pain Measurement
  • Phenylbutazone / pharmacology
  • Rats
  • Structure-Activity Relationship
  • Tetrazoles / chemical synthesis*
  • Tetrazoles / pharmacology

Substances

  • Analgesics
  • Anti-Inflammatory Agents
  • Indans
  • Tetrazoles
  • Aminopyrine
  • Carrageenan
  • Phenylbutazone
  • Acetic Acid
  • Indomethacin