Document Detail


Design and synthesis of bridged gamma-lactams as analogues of beta-lactam antibiotics.
MedLine Citation:
PMID:  15109638     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Anti-Bredt bridged bicyclo[3.2.1] gamma-lactams were designed as inhibitors of penicillin binding proteins (PBPs). The compounds were prepared by a carbenoid insertion into a lactam N-H bond. Their weak antibacterial activity could either be explained by a poor chemical stability or by unfavorable steric interactions of the methylene bridge of the gamma-lactam with the targeted enzymes.
Authors:
Jozsef Aszodi; David A Rowlands; Pascale Mauvais; Pascal Collette; Alain Bonnefoy; Maxime Lampilas
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Bioorganic & medicinal chemistry letters     Volume:  14     ISSN:  0960-894X     ISO Abbreviation:  Bioorg. Med. Chem. Lett.     Publication Date:  2004 May 
Date Detail:
Created Date:  2004-04-27     Completed Date:  2004-12-22     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9107377     Medline TA:  Bioorg Med Chem Lett     Country:  England    
Other Details:
Languages:  eng     Pagination:  2489-92     Citation Subset:  IM    
Affiliation:
Medicinal Chemistry, Aventis pharma, 102, route de Noisy, 93235 Romainville Cedex, France.
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MeSH Terms
Descriptor/Qualifier:
Anti-Bacterial Agents / chemical synthesis*,  pharmacology
Bicyclo Compounds, Heterocyclic / chemical synthesis,  pharmacology
Drug Design
Drug Stability
Gram-Negative Bacteria / drug effects
Gram-Positive Bacteria / drug effects
Inhibitory Concentration 50
Lactams / chemical synthesis*,  pharmacology
Microbial Sensitivity Tests
Penicillin-Binding Proteins / antagonists & inhibitors
Structure-Activity Relationship
beta-Lactamases / antagonists & inhibitors
Chemical
Reg. No./Substance:
0/Anti-Bacterial Agents; 0/Bicyclo Compounds, Heterocyclic; 0/Lactams; 0/Penicillin-Binding Proteins; EC 3.5.2.6/beta-Lactamases

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


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