N-thiolated β-lactam antibacterials: Defining the role of unsaturation in the C4 side chain

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 2, 2003, Pages 193-196

  Coates, Cristina ^a   Long, Timothy E ^a   Turos, Edward ^a   Dickey, Sonja ^a   Lim, Daniel V ^a  

^a UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM ANTIBIOTIC; BETA LACTAM DERIVATIVE; N METHYLTHIOLACTAM DERIVATIVE; THIOL DERIVATIVE; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT; BETA LACTAM;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL GROWTH; DRUG MECHANISM; GROWTH INHIBITION; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MICROCOCCUS LUTEUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS; STAPHYLOCOCCUS SAPROPHYTICUS; STAPHYLOCOCCUS SIMULANS; STRUCTURE ACTIVITY RELATION; CHEMISTRY; DRUG EFFECT; MICROBIOLOGICAL EXAMINATION; PENICILLIN RESISTANCE; STAPHYLOCOCCUS;

ANTI-BACTERIAL AGENTS; BETA-LACTAMS; METHICILLIN RESISTANCE; MICROBIAL SENSITIVITY TESTS; STAPHYLOCOCCUS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFHYDRYL COMPOUNDS;

EID: 0037449351     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(02)00383-8     Document Type: Article

References (8)

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3. Ren X.-F., Konaklieva M.I., Turos E. J. Org. Chem. 60:1995;4980.
4. Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds., Academic Press: New York, 1982, Volumes 1-3.
5. Turos, E.; Long, T. E.; Konaklieva, M. I.; Coates, C.; Shim, J.-Y.; Dickey, S.; Lim, D. V.; Cannons, A. Bioorg. Med. Chem. Lett. 2002, 12, 2229.
6. Woulfe S.R., Iwagami H., Miller M.J. Tetrahedron Lett. 26:1985;3891.
7. This postulated S-demethylation would resemble that which occurs in vivo in the transfer of S-adenosylmethionine to nitrogen bionucleophiles.
8. Shah, N. V.; Cama, L. D. Heterocycles 1987, 25, 221. Likewise, we have observed in solution studies that the N-methylthio lactams react with glutathione via transfer of the methylthio group with N-S bond cleavage.