| 5-sulfamoylorthanilic acids, a sulfonamide series with salidiuretic activity. | |
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MedLine Citation:
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PMID: 6876086 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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K Sturm; R Muschaweck; M Hropot |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Journal of medicinal chemistry Volume: 26 ISSN: 0022-2623 ISO Abbreviation: J. Med. Chem. Publication Date: 1983 Aug |
Date Detail:
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Created Date: 1983-09-09 Completed Date: 1983-09-09 Revised Date: 2003-11-14 |
Medline Journal Info:
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Nlm Unique ID: 9716531 Medline TA: J Med Chem Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 1174-87 Citation Subset: IM |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Animals Diuresis / drug effects* Dogs Furosemide / analogs & derivatives*, chemical synthesis Glomerular Filtration Rate / drug effects Natriuresis / drug effects |
| Chemical | |
Reg. No./Substance:
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54-31-9/Furosemide |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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