Synthesis and antiallergic properties of some 4H,5H-pyrano[3,2-c][1]benzopyran-4-one, 4H,5H-[1]benzothiopyrano[4,3-b]pyran-4-one, and 1,4-dihydro-5h-[1]benzothiopyrano[4,3-b]pyridin-4-one derivatives

J Med Chem. 1980 Dec;23(12):1372-6. doi: 10.1021/jm00186a016.

Abstract

A series of novel 2-carboxylic acids of the title ring systems has been synthesized from the corresponding 3-acetyl-4H-[1]benzopyran-4-one and benzothiopyran-4-one. These acids were examined for their ability to inhibit the rat passive cutaneous anaphylaxis; the pyridinone carboxylic acids 6 displayed a higher degree of iv and ip anaphylactic activities than their pyranone analogues 5. The potassium salt 5a (R6 = K) was the only compound that exhibited a moderate oral activity.

MeSH terms

  • Animals
  • Benzopyrans / chemical synthesis*
  • Benzopyrans / pharmacology
  • Chemical Phenomena
  • Chemistry
  • Hypersensitivity / drug therapy*
  • Male
  • Passive Cutaneous Anaphylaxis / drug effects
  • Rats

Substances

  • Benzopyrans