Synthesis and biological activity of novel penem sulfoxides and sulfones

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 17, 1997, Pages 2217-2222

  Pfaendler, Hans Rudolf ^a   Weishaupt, Ralf ^a   Medicus, Claus ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

PENEM DERIVATIVE; SULFONE DERIVATIVE;

ARTICLE; DRUG ACTIVITY; DRUG STABILITY; DRUG SYNTHESIS; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030961147     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00401-0     Document Type: Article

References (13)

1. Pfaendler H. R.; Medicus C. Bioorg. Med. Chem. Lett. 1997, 7, 623. See also corrected configuration in Bioorg. Med. Chem. Lett. 1997, 7, 757.
2. Pfaendler H. R.; Medicus C. Bioorg. Med. Chem. Lett. 1997, 7, 623. See also corrected configuration in Bioorg. Med. Chem. Lett. 1997, 7, 757.
3. Gorman M.; Ryan C. W. In Cephalosporins and Penicillins; Flynn E. H., Ed.; Academic Press: New York, 1982; p 577.
4. Campoli-Richards D. M.; Brogden R. N. Drugs 1987, 53, 577.
5. de Koning J. J.; Marx A. F.; Poot M. M.; Smid P. M.; Verweij J. In Recent Advances in the Chemistry of β-Lactam Antibiotics, Elks J., Ed.; The Chemical Society, London, 1976; pp 161-166.
6. Dürckheimer W.; Klesel N.; Limbert M.; Schrinner E.; Seeger K.; Seliger H. In Recent Advances in the Chemistry of β-Lactam Antibiotics; Gregory G. I., Ed.; The Royal Society of Chemistry, London, 1980; pp 46-56.
7. Lombardi P.; Franceschi G.; Arcamone F. Tetrahedron Lett., 1979, 39, 3777.
8. Tanaka R.; Oyama Y.; Ishiguro M. J. Chem. Soc., Chem. Commun., 1990, 853.
9. 3, J = 6.5 Hz); 1.25 (s, 9H, tBu), 3.64 (dd, 1H, 6-H, J = 3.1 Hz, J = 4.9 Hz); 4.34 (m, 1H, 1′-H); 5.00 (d, 1H, 5-H, J = 3.1 Hz).
10. The sulfone esters 5a and 5b decomposed on tlc and should be investigated by irspectroscopy. Column chromatography is possible with low yields at room temperature. Yields were substantially increased by low temperature chromatography. Mass spectra were consistent with structures 5a and 5b.
11. 3CN / 3:1).
12. 1. The sulfide as well as the sulfoxide in this series were not significantly active, nor as antibacterials, neither as β-lactamase inhibitors.
13. The β-lactamases were available by the Sigma Chemical Co. (P 4524 type IV and P 3553).