Dipolar cycloaddition of novel 6-(nitrileoxidomethyl) penam sulfone: An efficient route to a new class of β-lactamase inhibitors

Organic Letters

Volumn 2, Issue 20, 2000, Pages 3087-3090

  Sandanayaka, Vincent P ^a   Yang, Youjun ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6 (NITRILEOXIDOMETHYL) PENAM SULFONE; 6-(NITRILEOXIDOMETHYL) PENAM SULFONE; BETA LACTAMASE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ENZYME INHIBITOR; ISOXAZOLE DERIVATIVE; NITRILE; SULFONE;

ARTICLE; CHEMISTRY; CYCLIZATION; DRUG ANTAGONISM; STEREOISOMERISM; SYNTHESIS;

BETA-LACTAMASES; CYCLIZATION; ENZYME INHIBITORS; INDICATORS AND REAGENTS; ISOXAZOLES; NITRILES; STEREOISOMERISM; SULFONES;

EID: 0034609667     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006256r     Document Type: Article

References (30)

1. (a) Tenover, F. C. JAMA 1996, 275, 300.
2. (b) Nikaido, H. Antimicrob. Agents Chemother. 1989, 33, 1831.
3. (c) Davies, J. Science 1994, 264, 360.
4. (d) Neu, H. Science 1992, 257, 1064.
5. (e) Marcaretti, O. A.; Danelon, G. O.; Setti, E. L.; Laborde, M.; Mata, E. G. Curr. Pharm. Des. 1999, 5, 939.
6. (f) Yang, Y.; Rasmussen, B. A.; Shlaes, D. M. Pharmacol. Ther. 1999, 83, 141.
7. (g) Payne, D. J.; Du, W.; Bateson, J. H. Exp. Opin. Invest. Drugs 2000, 9, 247.
8. (a) Durckheimer, W.; Blumbach, J.: Lattrell, R.; Scheunemann, K. H. Angew. Chem., Int. Ed. Engl. 1985, 24, 180.
9. (b) Maiti, S. N.; Phillips, O. A.; Micetich, R. G.; Livermore, D. M. Curr. Med. Chem. 1998, 5, 441.
10. Knowles, J. R. Acc. Chem. Res. 1993, 31 (Suppl A), 9.
11. (a) English, A. R.; Retsema, J. A.; Girard, A. E.; Lynch, J. E.; Barth, W. E. Antimicrob. Agents Chemother. 1978, 14, 414.
12. (b) Brenner, D. J.; Knowles, J. R. Biochemistry 1981, 20, 3681.
13. (a) Pratt, R. F. In The Chemistry of β-Lactams; Page, M. I., Ed.; Blackie Academic & Professional: Glascow, 1992; pp 229-271.
14. (b) Livermore, D. M. J. Antimicrob. Chemother. 1993, 31 (Suppl. A), 9-21.
15. (c) Bush, K.; Macalintal, C.; Rasmussen, B. A.; Lee, V. J.; Yang, Y. Antimicrob. Agents Chemother. 1993, 37, 851.
16. For a comprehensive account on the mechanism, see; Silverman, R. B. In Mechanism-Based Enzyme Inactivation: Chemistry and Enzymology; CRC press: Boca Raton, 1988.
17. (a) Brenner, D. J.; Knowles, J. R. Biochemistry 1981, 20, 3681.
18. (b) Fisher, J.; Charnas, R. L.; Bradley, S. M.; Knowles, J. R. Biochemistry 1981, 20, 2726.
19. (a) Ziegler, C.; Fabio, P.; Bush, K.; Steinberg, D. U.S. Patent 5 488 106, 1996.
20. (b) Chen, Y. L. U.S. Patent 4 826 833, 1989, and U.S. Patent 5 015 473, 1991.
21. Hanessian, S.; Alpegiani, M. Tetrahedron 1989, 45, 941.
22. Caramella, P.; Grunanger, P. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A.; Ed.; Willey-Interscience: 1984; Vol. 1, pp 291-392.
23. Volkman, R. A.; Caroll, R. D.; Drolet, R. B.; Elliott, M. L.; Moore, B. S. J. Org. Chem. 1982, 47, 3344.
24. Liu, K. C.; Shelton, B. R.; Howe, R. K. J. Org. Chem. 1980, 45, 3916.
25. Moriya, O.; Urata, Y.; Endo, T. J. Chem. Soc., Chem. Commun. 1991, 17.
26. All new compounds were fully characterized (NMR, IR, HRMS/ MS). These data are included in the Supporting Information.
27. Coppola, G. M.; Damon, R. E. Synth. Commun. 1993, 23(14), 2003.
28. (a) Houk, K. N.; Sims, J.; Duke, R. E.; Strozier, R. W.; George, J. K. J. Am. Chem. Soc. 1973, 95, 7287.
29. (b) Sustmann, R.; Trill, H. Angew. Chem., Int. Ed. Engl. 1972, 11, 838.
30. For details about the assay and experimental procedure, see: Bush, K.; Macalintal, C.; Rasmussen, B. A.; Lee, V. J.; Yang, Y. Antimicrob. Agents Chemother. 1993, 37, 851.