Synthesis and biological activities of an α-methyl and a β-methyl carbapenem and the corresponding unsubstituted compound

Bioorganic and Medicinal Chemistry Letters

Volumn 10, Issue 12, 2000, Pages 1389-1391

  Pfaendler, Hans Rudolf ^a   Weishaupt, Ralf ^a   Meffert, Helmut ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAMASE; CARBAPENEM DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG INHIBITION; DRUG SYNTHESIS; ENTEROBACTER CLOACAE; ENZYME INHIBITION; ESCHERICHIA COLI; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS;

ANTI-BACTERIAL AGENTS; CARBAPENEMS; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; MICROBIAL SENSITIVITY TESTS;

ENTEROBACTER CLOACAE; ESCHERICHIA COLI; PSEUDOMONAS; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS;

EID: 0034686521     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(00)00248-1     Document Type: Article

References (17)

1. Dürckheimer W., Blumbach J., Latrell R., Scheunemann K.H. Angew. Chem. 97:1985;183.
2. Shih D.H., Cama L., Christensen B.G. Heterocycles. 21:1984;29.
3. Shih D.H., Cama L., Christensen B.G. Tetrahedron Lett. 26:1985;587.
4. Sumita J., Nouda H., Shinagawa H., Yamaga H., Sunagawa M. J. Antibiot. 48:1995;188.
5. Sunagawa M., Sasaki A., Matsumura H., Goda K., Tamoto K. Chem. Pharm. Bull. 42:1994;1381.
6. Ratcliffe R.W., Salzmann T.N., Christensen B.G. Tetrahedron Lett. 21:1980;31.
7. 3); 4.21 (m, 1H, 1′-H).
8. 3CN/3:1.
9. Pfaendler H.R., Gosteli J., Woodward R.B., Rihs G. J. Am. Chem. Soc. 103:1981;4526.
10. Cohen N.C. J. Med. Chem. 26:1983;259.
11. Burton G. Bioorg. Med. Chem. Lett. 3:1993;2329.
12. f=0.42 (EtOAc).
13. (a) Uri, J. V.; Actor, P.; Weisbach, J. A. J. Antibiot. 1978, 31, 789.
14. (b) O'Callaghan, C. H.; Morris, A.; Kirby, S.; Shingler, A. H. Antimicrob. Agents and Chemother. 1972, 1, 283.
15. The β-lactamases were available from Sigma Chemical Co. (P 4524 type IV and P 3553).
16. Pfaendler H.R., Medicus C. Bioorg. Med. Chem. Lett. 7:1997;623.
17. Pfaendler H.R., Weishaupt R., Medicus C. Bioorg. Med. Chem. Lett. 7:1997;2217.