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...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1987-04, Vol.30 (4), p.591-597
Main Authors: Ponticello, Gerald S, Freedman, Mark B, Habecker, Charles N, Lyle, Paulette A, Schwam, Harvey, Varga, Sandor L, Christy, Marcia E, Randall, William C, Baldwin, John J
Format: Article
Language:English
Subjects:
Carbonic Anhydrase Inhibitors - chemical synthesis
Carbonic Anhydrase Inhibitors - pharmacology
Chemical Phenomena
Chemistry
Erythrocytes - enzymology
Exact sciences and technology
Glaucoma - drug therapy
Heterocyclic compounds
Heterocyclic Compounds - pharmacology
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Humans
Organic chemistry
Preparations and properties
Solubility
Structure-Activity Relationship
Sulfonamides - pharmacology
Water
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Summary: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.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00387a002