Trifluoromethyl alcohol and ketone inhibitors of metallo-β-lactamases

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 20, 1996, Pages 2455-2458

  Walter, Magnus W ^a   Felici, Antonio ^c   Galleni, Moreno ^b   Soto, Raquel Paul ^b   Adlington, Robert M ^a   Baldwin, Jack E ^a   Frère, Jean Marie ^b   Gololobov, Mikhail ^b   Schofield, Christopher J ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF LIÈGE   (Belgium)

^c UNIVERSITY OF L'AQUILA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAMASE; BETA LACTAMASE INHIBITOR; KETONE;

ARTICLE; BACILLUS CEREUS; CHIRALITY; DRUG SYNTHESIS; ENZYME INHIBITION; PSEUDOMONAS AERUGINOSA; SPECTROPHOTOMETRY; STENOTROPHOMONAS MALTOPHILIA; STRUCTURE ACTIVITY RELATION;

BACILLUS CEREUS; PSEUDOMONAS; PSEUDOMONAS AERUGINOSA; STENOTROPHOMONAS MALTOPHILIA;

EID: 0030598201     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00453-2     Document Type: Article

References (29)

1. 1. Frère, J.-M. Molecular Microbiology 1995, 16, 385-395.
2. 2. Waley, S.G. In The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992; pp. 198-228.
3. 3. Waley, S.G. In The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992; pp. 229-263.
4. 4. Felici, A.; Amicosante, G.; Oratore, A.; Strom, R.; Ledent, P.; Joris, B.; Fanuel, L.; Frère, J.-M. Biochem. J. 1993, 291, 151-155.
5. 5. Carfi, A.; Pares, S.; Duée, E.; Galleni, M.; Duez, C.; Frère, J.-M.; Dideberg; O. EMBO J. 1995, 14, 4914-4921.
6. 6. Gilpin, L. M.; Fulston, M.; Payne, D.; Cramp, R.; Hood, I. J. Antibiotics 1995, 48, 1081-1085.
7. 7. (a) Gelb, M. H.; Svaren, J. P.; Abeles, R. H. Biochemistry 1985, 24, 1813-1817.
8. (b) Brady, K.; Wei, A.; Ringe, D.; Abeles, R. H. Biochemistry 1990, 29, 7600-7607.
9. 8. Christianson, D. W.; Lipscomb, W. N. J. Am. Chem. Soc. 1986, 108, 4998-5003.
10. 9. Crompton, I. E. D. Phil. Thesis, Oxford, 1988.
11. 10. (a) Kolb, M.; Barth, J.; Neises, B. Tetrahedron Lett. 1986, 27, 1579-1582.
12. (b) Boivin, J.; El Kaim, L.; Zard, S. Z. Tetrahedron 1995, 51, 2573-2584.
13. (c) for a review see: McClinton, M.A.; McClinton, D.A. Tetrahedron 1992, 48, 6555-6666.
14. 11. (a) Imperiali, B.; Abeles, R. H. Tetrahedron Lett. 1986, 27, 135-138.
15. (b) Patel, D. V.; Rielly-Gauvin, K.; Ryone, D. E. Tetrahedron Lett. 1988, 29, 4665-4668.
16. (c) Edwards, P. D. Tetrahedron Lett. 1992, 33, 4279-4282.
17. (d) Skyles, J. W. et. al. J. Med. Chem. 1992, 35, 641-662.
18. 12. Walter, M. W.; Adlington, R. M.; Baldwin, J. E.; Chuhan, J.; Schofield, C. J. Tetrahedron Lett. 1995, 36, 7761-7764.
19. 13. Ruppert, I.; Schlich, K.; Volbach, W. Tetrahedron Lett. 1984, 25, 2195-2198.
20. 14. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815-3818.
21. 13C-NMR analysis.
22. 16. (a) Krishnamurti, R.; Bellow, D. R.; Surya Prakash, G. K. J. Org. Chem. 1991, 56, 984-989.
23. (b) Ramaiah, P.; Krishnamurti, R.; Surya Prakash, G. K. Organic Synthesis 1995, 232-240.
24. 17. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
25. 18. Silica gel chromatography resulted in low recovery of products 5.
26. 19. Hiskey, R. G.; Jung, J. M. J. Am. Chem. Soc. 1963, 85, 578-582.
27. 14 and showed no significant activity as inhibitors of the four metallo-β-lactamases tested.
28. 21. De Meester, F.; Joris, B.; Reckinger, B.; Bellefroid-Bourguignon, C.; Frère, J.-M.; Waley, S. G. Biochem. Pharmacol. 1987, 36, 2393-2403.
29. 22. Matagne, A.; Misselyn-Baudin, A.-M.; Joris, B.; Epircum, T.; Granier, B.; Frère, J.-M. Biochem. J. 1990, 265, 131-146.