Structure-based design of β-lactamase inhibitors. 2. Synthesis and evaluation of bridged sulfactams and oxamazins

Journal of Medicinal Chemistry

Volumn 41, Issue 21, 1998, Pages 3972-3975

  Hubschwerlen, Christian ^a   Angehrn, Peter ^a,b   Gubernator, Klaus ^a   Page, Malcolm G P ^a   Specklin, Jean Luc ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

^b Formerly CombiChem Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAMASE INHIBITOR; PENICILLINASE; SODIUM [2 (4 CARBAMOYLPHENYLCARBAMOYL) 7 OXO 2,6 DIAZABICYCLO[3.2.0]HEPTAN 6 YL]SULFATE; SODIUM [2 (TERT BUTOXYCARBONYL) 7 OXO 2,6 DIAZABICYCLO[3.2.0]HEPTAN 6 YL]SULFATE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ASSAY; ENZYME INHIBITION; MINIMUM INHIBITORY CONCENTRATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

ACETIC ACIDS; BETA-LACTAMASES; BETA-LACTAMS; CEFTRIAXONE; CEPHALOSPORINS; CITROBACTER FREUNDII; DRUG DESIGN; DRUG SYNERGISM; ENZYME INHIBITORS; ESCHERICHIA COLI; KINETICS; PSEUDOMONAS AERUGINOSA; SULFONIC ACIDS;

EID: 0032497590     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9800245     Document Type: Article

References (10)

1. Heinze-Krauss, I.; Angehrn, P.; Charnas, R. L.; Gubernator, K.; Gutknecht, E.; Hubschwerlen, C.; Kania, M.; Oefner, C.; Page, M. G. P.; Sogabe, S.; Specklin. J.-L.; Winkler, F. K. Structure-based design of β-Lactamase Inhibitors. 1. Synthesis and Evaluation of Bridged Monobactams. J. Med. Chem. 1998, 41, 3961-3971.
2. Livermore, D. M.; Chen, H. Y. Potentiation of β-Lactams against Pseudomonas aeruginosa strains by Ro 48-1256, a bridged monobactam inhibitor of AmpC β-lactamases. J. Antimicrob. Chemother. 1997, 40, 335-343.
3. Girard, S.; Doslongchamp, P. Formation of 14-membered Carbocycles by Intramolecular Michael Addition on Ynones and Enones. Can. J. Chem. 1992, 70, 1265-1273.
4. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. Catalytic Asymmetrie Epoxidation and Kinetic Resolution: Modified Procedures Including in situ Derivatization. J. Am. Chem. Soc. 1987, 109, 5765-5780.
5. Miller, M.; Mattingly, P. G.; Morrison, M. A.; Kerwin, J. R., Jr.; Synthesis of β-Lactams from Substituted Hydroxamic Acids. J. Am. Chem. Soc. 1980, 102, 7026-7032.
6. Breuer, H.; Straub, H.; Treuner, U. D.; Drossard, J.-M.; Höhn, H.; Lindner, K. R. [(2-Oxo-1-azetidinyl)oxy]acetic Acids: A New Class of Synthetic Monobactams. J. Antibiot. 1985, 38, 813-818.
7. Smith, A. B., III; Branca, S. J.; Guarciaro, M. A.; Wovkulich, P. M.; Korn, A. 2-Hydroxymethyl-2-cyclopentenone. In Organic Synthettin; Stevens, R. V., Ed.; J. Wiley and Sons: New York, 1983, Vol. 61, pp 65-70.
8. Belleteni, J. R.; Miller, M. J. A Short Synthesis of an Important Precursor to a New Class of Bicyclic β-Lactamase Inhibitors. Tetrahedron Lett. 1997, 38, 167-168.
9. Page, M. G. P. The Kinetics of Non-Stoichiometric Bursts of β-Lactam Hydrolysis Catalysed by Class C β-Lactamases. Biochem. J. 1993, 295, 295-304.
10. Heinze-Krauss, I.; Angehrn, P.; Guerry, P.; Hebeisen, P.; Hubschwerlen, C.; Kompis, I.; Page, M. G. P.; Richter, H. G. F.; Runtz, V.; Stalder, H.; Weiss, U.; Wei, C.-C. Synthesis and Structure-Activity Relationship of (Lactamylvinyl)cephalosporins Exhibiting Activity against Staphylococci, Pneumococci, and Enterococci. J. Med. Chem. 39, 1864-1871.