Thienothiopyran-2-sulfonamides: a novel class of water-soluble carbonic anhydrase inhibitors.
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.
D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D004912:Erythrocytes / Q000201:enzymology; D005901:Glaucoma / Q000188:drug therapy; D006571:Heterocyclic Compounds / Q000494:pharmacology*; D006801:Humans; D012995:Solubility; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000494:pharmacology*; D014867:Water
D002257:Carbonic Anhydrase Inhibitors; D006571:Heterocyclic Compounds; D013449:Sulfonamides; D014867:Water