Studies on hindered phenols and analogues. 2. 1,3-Benzoxathioles having SRS-A inhibiting activity

J Med Chem. 1990 May;33(5):1491-6. doi: 10.1021/jm00167a032.

Abstract

A series of hindered phenolic 1,3-benzoxathioles (7a-l) were prepared and investigated for biological properties. Many compounds had LPO-lowering, antisuperoxide inhibiting, SRS-A inhibiting, and 5-lipoxygenase inhibiting activities. Among them, 5-hydroxy-4,6,7-trimethyl-2-propyl-1,3-benzoxathiole (7d) and 3-(5-hydroxy-4,6,7-trimethyl-1,3-benzoxathiol-2-yl)propanol (7j) were most potent in SRS-A inhibiting and 5-lipoxygenase inhibiting activities, respectively, and were selected for further development as candidate drugs for the treatment of asthma.

MeSH terms

  • Animals
  • Asthma / drug therapy*
  • Benzoxazoles / chemical synthesis*
  • Benzoxazoles / pharmacology
  • Chemical Phenomena
  • Chemistry
  • Guinea Pigs
  • Lipid Peroxidation / drug effects
  • Lipoxygenase Inhibitors
  • Mice
  • Mice, Inbred C57BL
  • SRS-A / antagonists & inhibitors*
  • Structure-Activity Relationship

Substances

  • Benzoxazoles
  • Lipoxygenase Inhibitors
  • SRS-A
  • 5-hydroxy-4,6,7-trimethyl-2-propyl-1,3-benzoxathiazole
  • 3-(5-hydroxy-4,6,7-trimethyl-1,3-benzoxathiazol-2-yl)propanol