Studies on v-triazoles. 7. Antiallergic 9-oxo-1H,9H-benzopyrano[2,3-d]-v-triazoles

J Med Chem. 1983 Feb;26(2):251-4. doi: 10.1021/jm00356a025.

Abstract

A series of the little compounds was prepared by cyclization of the appropriate 5-(aryloxy)-v-triazole-4-carboxylic acids and evaluated for antiallergic activity by the rat passive cutaneous anaphylaxis (PCA) screen. The most potent compounds were 6-(mesyloxy)-9-oxo-1H,9H-benzopyrano[2,3-d]-v-triazole and its 5-methyl homologue, which were some tenfold more potent than disodium cromoglycate. Dialkyl derivatives, especially those substituted at C-5 and C-6 or C-6 and C-7, and 6-methoxy compounds were also among the more potent compounds. One compound, 6,7-dimethyl-9-oxo-1H,9H-benzopyrano[2,3-d]-v-triazole, was further evaluated and shown to be a potent inhibitor of rat PCA when given orally.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Benzopyrans / chemical synthesis*
  • Benzopyrans / therapeutic use
  • Histamine H1 Antagonists / chemical synthesis*
  • Indicators and Reagents
  • Male
  • Passive Cutaneous Anaphylaxis
  • Rats
  • Rats, Inbred Strains
  • Structure-Activity Relationship
  • Triazines / chemical synthesis*
  • Triazines / therapeutic use

Substances

  • Benzopyrans
  • Histamine H1 Antagonists
  • Indicators and Reagents
  • Triazines