Document Detail

Antibacterial activity and chemical reactivity of sulphanylamides. Rate constants of alkaline hydrolysis of N4-acetylsulphanylamides.
MedLine Citation:
PMID:  631319     Owner:  NLM     Status:  MEDLINE    
The alkaline deacylation rate constants of a collection of N4-acetylderivatives of acidic and non-acidic sulphonamides (SA) clearly show a definite trend due to the intramolecular effects induced by the different substitutions on the N1 nitrogen. The rate constant is interpreted as a reactivity index of the corresponding non-acetylated compound, and is found to be strictly correlated with the electron-availability of the p-amino group; thus providing an interesting correlation with the antibacterial activity of these drugs. Moreover, the reported experiments corroborate early predictions that the greatest reactivity of the p-amino group pertains to p-aminobenzoate (PAB) in the series of chemically related compounds, and that SA anions show the highest chemical and electronic resemblance to the essential metabolite (PAB); thus the high antibacterial activity of SA anions correctly corresponds to its close resemblance to the metabolite.
A Albasini; G Vampa; P Pecorari; A Rastelli; P G De Benedetti
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Il Farmaco; edizione scientifica     Volume:  33     ISSN:  0430-0920     ISO Abbreviation:  Farmaco Sci     Publication Date:  1978 Feb 
Date Detail:
Created Date:  1978-05-08     Completed Date:  1978-05-08     Revised Date:  2009-06-05    
Medline Journal Info:
Nlm Unique ID:  0370716     Medline TA:  Farmaco Sci     Country:  ITALY    
Other Details:
Languages:  eng     Pagination:  142-7     Citation Subset:  IM    
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MeSH Terms
Bacteria / drug effects*
Indicators and Reagents
Structure-Activity Relationship
Sulfanilamides / analysis,  pharmacology*
Reg. No./Substance:
0/Alkalies; 0/Indicators and Reagents; 0/Protons; 0/Sulfanilamides

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

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