Document Detail

5-sulfamoylorthanilic acids, a sulfonamide series with salidiuretic activity.
MedLine Citation:
PMID:  6876086     Owner:  NLM     Status:  MEDLINE    
A series of 4,N-disubstituted 5-sulfamoylorthanilic acids was synthesized by nucleophilic substitution reactions starting either from 2,4-dihalogeno-5-sulfamoylbenzenesulfonic acids or, in most cases, from phenyl 2,4-dihalogeno-5-sulfamoylbenzenesulfonates. The latter method is based on the relative stability of the phenoxysulfonyl group to nucleophiles, e.g., amines, phenols, and thiols, and the possibility of smooth hydrolytic or hydrogenolytic cleavage as a final step, with formation of the SO3H group. On evaluation of these compounds for salidiuretic activity in rats orally (po), and in dogs orally and intravenously (iv), a number of highly active substances was found; the best had a threshold dose of 0.02 mg/kg po in dogs. The results are given in tables, and the structure-activity relationships within the series are discussed. Besides the known effect of the phenoxy radical, an outstanding activating effect was shown by the butylsulfonyl and cycloalkylsulfonyl radicals and by the N-methylanilino radical in particular when they were located in the 4-position of the orthanilic acid molecule. The sulfanilic acid isomers corresponding to three of the most active compounds were synthesized and proved to be completely inactive in rats.
K Sturm; R Muschaweck; M Hropot
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of medicinal chemistry     Volume:  26     ISSN:  0022-2623     ISO Abbreviation:  J. Med. Chem.     Publication Date:  1983 Aug 
Date Detail:
Created Date:  1983-09-09     Completed Date:  1983-09-09     Revised Date:  2003-11-14    
Medline Journal Info:
Nlm Unique ID:  9716531     Medline TA:  J Med Chem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  1174-87     Citation Subset:  IM    
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MeSH Terms
Diuresis / drug effects*
Furosemide / analogs & derivatives*,  chemical synthesis
Glomerular Filtration Rate / drug effects
Natriuresis / drug effects
Reg. No./Substance:

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