Document Detail

Aminobenzioc acid diuretics. 8.(2) 3, 4-Disubstituted 5-methylsulfonylbenzioc acids and related compounds.
MedLine Citation:
PMID:  1255664     Owner:  NLM     Status:  MEDLINE    
Various 2, 4- and 3, 4-disubstituted 5-methylsulfonylbenzoic acids were synthesized as methylsulfonyl analogues of previously described 5-sulfamoylbenzoic acid diuretics. The results of the diuretic screening in dogs reveal that substitution of the sulfamoyl group by the spatially and sterically similar methylsulfonyl group does not affect the diuretic pattern but leads generally to somewhat decreased potency. For the highly potent 3-benzylamino-4-phenoxy-5-methylsulfonylbenzoic acid the corresponding 5-methylthio and 5-methylsulfinyl analogs were prepared and found still to exhibit diuretic activity. Internal aldol condensation and subsequent dehydration of 3-benzylamino-and 3-n-butylamino-4-benzoyl-5-methylsulfonylbenzoic acid provided the corresponding inactive 4-alkylamino-6-carboxy-2, 3-dihydro-3-hydroxy-3-phenylbenzo[b]thiophene 1, 1-dioxides and 4-alkylamino-6-carboxy-3-phenyl-benzo[b]thiophene 1,1-dioxides.
P W Feit; O B Nielsen
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of medicinal chemistry     Volume:  19     ISSN:  0022-2623     ISO Abbreviation:  J. Med. Chem.     Publication Date:  1976 Mar 
Date Detail:
Created Date:  1976-05-25     Completed Date:  1976-05-25     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:  402-6     Citation Subset:  IM    
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MeSH Terms
Aminobenzoic Acids / chemical synthesis*,  pharmacology
Chlorides / urine
Diuresis / drug effects
Potassium / urine
Sodium / urine
Structure-Activity Relationship
Sulfones / chemical synthesis,  pharmacology
Reg. No./Substance:
0/Aminobenzoic Acids; 0/Chlorides; 0/Sulfones; 7440-09-7/Potassium; 7440-23-5/Sodium

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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