Cerebrovasodilatation through selective inhibition of the enzyme carbonic anhydrase. 3. 5-(Arylthio)-, 5-(arylsulfinyl)-, and 5-(arylsulfonyl)thiophene-2-sulfonamides

J Med Chem. 1981 Aug;24(8):959-64. doi: 10.1021/jm00140a009.

Abstract

A series of 5-(arylthio)-, 5-(arylsulfinyl)-, and 5-(arylsulfonyl)thiophene-2-sulfonamides is described and anticonvulsant activities are listed for the compounds. In most cases, the sulfones had the highest activity and the sulfides the least. Sulfones with 3- or 4-halo substituents generally had the highest activity, and one analogue, 5-[(4-fluorophenyl)sulfonyl]thiophene-2-sulfonamide (51, UK-17022), had an anticonvulsant ED50 fo 2 mg/kg when administered orally to mice. Compound 51 selectively increased cerebral blood flow in animals without an unacceptable level of diuresis.

MeSH terms

  • Animals
  • Anticonvulsants*
  • Brain / blood supply
  • Brain / enzymology
  • Carbonic Anhydrase Inhibitors*
  • Carbonic Anhydrases / metabolism
  • Erythrocytes / enzymology
  • Male
  • Mice
  • Regional Blood Flow
  • Structure-Activity Relationship
  • Sulfonamides / pharmacology*
  • Thiophenes / pharmacology*

Substances

  • Anticonvulsants
  • Carbonic Anhydrase Inhibitors
  • Sulfonamides
  • Thiophenes
  • Carbonic Anhydrases