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

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 t...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1981-08, Vol.24 (8), p.959-964
Main Authors: Barnish, Ian T, Cross, Peter E, Dickinson, Roger P, Parry, Michael J, Randall, Michael J
Format: Article
Language:English
Subjects:
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
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Summary: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.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00140a009