N-Thiolated β-lactams: A new family of anti-Bacillus agents

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 8, 2006, Pages 2084-2090

  Turos, Edward ^a   Long, Timothy E ^a   Heldreth, Bart ^a   Leslie, J Michelle ^a   Reddy, G Suresh Kumar ^a   Wang, Yang ^a   Coates, Cristina ^a   Konaklieva, Monika ^a,c   Dickey, Sonja ^a   Lim, Daniel V ^a   Alonso, Eduardo ^b   Gonzalez, Javier ^b  

^a UNIVERSITY OF SOUTH FLORIDA   (United States)

^b UNIVERSITY OF OVIEDO   (Spain)

^c AMERICAN UNIVERSITY   (United States)

Author keywords

Antibiotics; Bacillus; N Thiolated lactams; SAR

Indexed keywords

ANTIINFECTIVE AGENT; BETA LACTAM ANTIBIOTIC; THIOL DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACILLUS ANTHRACIS; BACTERIAL GROWTH; BACTERIAL STRAIN; CONTROLLED STUDY; DRUG ACTIVITY; DRUG EFFECT; GROWTH INHIBITION; LIPOPHILICITY; NONHUMAN; STAPHYLOCOCCUS; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; BACILLUS; BACILLUS ANTHRACIS; BETA-LACTAMS; DRUG RESISTANCE, BACTERIAL; METHICILLIN RESISTANCE; MICROBIAL SENSITIVITY TESTS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFHYDRYL COMPOUNDS;

BACILLUS (BACTERIUM); BACILLUS ANTHRACIS; BACTERIA (MICROORGANISMS); STAPHYLOCOCCUS;

EID: 33644796914     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.01.070     Document Type: Article

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11. Spirocyclic lactam 1j was tested as a single enantiomer with absolute stereochemistry as shown.
12. 3-Derivatives 1r-t were synthesized with exclusive trans relative stereochemistry and tested as racemic mixtures.
13. Testing against the Ames strain of B. anthracis was performed at the Center for Biodefense, University of South Florida.
14. Lactams 5 and 6 were prepared and tested as mixtures of diastereomers in which the stereogenic centers within the sulfur side chains, and the β-lactam ring, are all racemic.