Thienothiopyran-2-sulfonamides: a novel class of water-soluble carbonic anhydrase inhibitors

J Med Chem. 1987 Apr;30(4):591-7. doi: 10.1021/jm00387a002.


An attempt to develop a water-soluble carbonic anhydrase inhibitor focused on exploring structure-activity relationships in the thienothiopyransulfonamide class. The strategy to influence water solubility while retaining carbonic anhydrase activity involved the introduction of a hydroxyl moiety and adjusting the oxidation state of the sulfur on the thiopyran portion of the molecule. Compounds 4 and 17 best fit the criteria of aqueous solubility and inhibitory potency vs. human carbonic anhydrase II and are candidates for evaluation as topically effective antiglaucoma agents.

Publication types

  • Comparative Study

MeSH terms

  • Carbonic Anhydrase Inhibitors / chemical synthesis*
  • Carbonic Anhydrase Inhibitors / pharmacology
  • Chemical Phenomena
  • Chemistry
  • Erythrocytes / enzymology
  • Glaucoma / drug therapy
  • Heterocyclic Compounds / pharmacology*
  • Humans
  • Solubility
  • Structure-Activity Relationship
  • Sulfonamides / pharmacology*
  • Water


  • Carbonic Anhydrase Inhibitors
  • Heterocyclic Compounds
  • Sulfonamides
  • Water