Syntheses and studies of new forms of N-sulfonyloxy β-lactams as potential antibacterial agents and β-lactamase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 23, Issue 18, 2015, Pages 6138-6147

  Carosso, Serena ^a   Miller, Marvin J ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

N Sulfonyloxy lactam; Oxidatative lactamization; Lactamase inhibitors

Indexed keywords

2 [[4 (BENZAMIDOMETHYL) 1H 1,2,3 TRIAZOL 1 YL]METHYL] 4 OXOAZETIDIN 1 YL 4 METHYLBENZENE SULFONATE; 2 [[4 [[2 CHLORO 5 (TRIFLUOROMETHYL)BENZAMIDO]METHYL] 1H 1,2,3 TRIAZOL 1 YL]METHYL] 4 OXOAZETIDIN 1 YL 4 METHYLBENZENE SULFONATE; 4 (BROMOMETHYL) 2 OXOAZETIDIN 1 YL 2 PHENYLETHENE 1 SULFONATE; 4 (BROMOMETHYL) 2 OXOAZETIDIN 1 YL 2,4 DINITROBENZENE SULFONATE; 4 (BROMOMETHYL) 2 OXOAZETIDIN 1 YL 2,4,6 TRIISOPROPYLBENZENE SULFONATE; 4 (BROMOMETHYL) 2 OXOAZETIDIN 1 YL 4 METHOXYBENZENE SULFONATE; 4 (BROMOMETHYL) 2 OXOAZETIDIN 1 YL 4 METHYLBENZENE SULFONATE; 4 (BROMOMETHYL) 2 OXOAZETIDIN 1 YL 4 NITROBENZENE SULFONATE; 4 (BROMOMETHYL) 2 OXOAZETIDIN 1 YL NAPHTHALENE 1 SULFONATE; 4 (BROMOMETHYL) 2 OXOAZETIDIN 1 YL NAPHTHALENE 2 SULFONATE; 4 (BROMOMETHYL) 2 OXOAZETIDIN 1 YL THIOPHENE 2 SULFONATE; 4 [[(4,5 DIHYDROTHIAZOL 2 YL)THIO]METHYL] 2 OXOAZETIDIN 1 YL 4 METHYLBENZENE SULFONATE; ANTIINFECTIVE AGENT; BETA LACTAM DERIVATIVE; BETA LACTAMASE; BETA LACTAMASE INHIBITOR; ETHYL 1 [[4 OXO 1 (TOXYLOXY)AZETIDIN 2 YL]METHYL] 1H 1,2,3 TRIAZOLE 4 CARBOXYLATE; N SULFONYLOXY BETA LACTAM DERIVATIVE; UNCLASSIFIED DRUG; BETA LACTAM;

ACINETOBACTER BAUMANNII; ANTIBACTERIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CYCLIZATION; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME INHIBITION; ESCHERICHIA COLI; MICROCOCCUS LUTEUS; MYCOBACTERIUM VACCAE; NONHUMAN; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; CHEMISTRY; DRUG EFFECTS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; KINETICS; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTI-BACTERIAL AGENTS; BETA-LACTAMASE INHIBITORS; BETA-LACTAMASES; BETA-LACTAMS; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; KINETICS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84940788125     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2015.08.005     Document Type: Article

References (29)

1. A.A. Medeiros Clin. Inf. Dis. 24 1997 S19
2. J.R. Knowles Acc. Chem. Res. 18 1985 97
3. I. Massova, and S. Mobashery Acc. Chem. Res. 30 1997 162
4. M.W. Crowder, J. Spencer, and A.J. Vila Acc. Chem. Res. 39 2006 721
5. Y. Yang, B.A. Rasmussen, and D.M. Shlaes Pharm. Ther. 83 1999 141
6. J.D. Buynak Biochem. Pharmacol. 71 2006 930
7. L.P. Kotra, and S. Mobashery Bull. Inst. Pasteur 96 1998 139
8. S.M. Drawa, and R.A. Bonomo Clin. Microbiol. Rev. 23 2010 160
9. K. Bush, and S. Mobashery B.P. Rosen, S. Mobashery, Resolving the Antibiotic Paradox: Progress in Understanding Drug Resistance and Development of New Antibiotics 1998 Plenum Press New York 71
10. M. Teng, and M.J. Miller Bioorg. Med. Chem. 1 1993 151
11. A. Bulychev, M.E. O'Brien, I. Massova, M. Teng, T.A. Gibson, M.J. Miller, and S. Mobashery J. Am. Chem. Soc. 117 1995 5938
12. L. Mourey, L.P. Kotra, J. Bellettini, A. Bulychev, M. O'Brien, M.J. Miller, S. Mobashery, and J.-P. Samana J. Biol. Chem. 274 1999 25260
13. P. Swarén, I. Massova, J.R. Bellettini, A. Bulychev, L. Maveyraud, L.P. Kotra, M.J. Miller, S. Mobashery, and J.-P. Samana J. Am. Chem. Soc. 121 1999 5353
14. A. Bulychev, J.R. Bellettini, M. O'Brien, P.J. Crocker, J.-P. Samana, M.J. Miller, and S. Mobashery Tetrahedron 56 2000 5719
15. G. Rajendra, and M.J. Miller Tetrahedron Lett. 26 1985 5385
16. G. Rajendra, and M.J. Miller J. Org. Chem. 52 1987 4471
17. Pfizer patent WO 2012/073138 A1, 2012.
18. S.R. Woulfe, and M.J. Miller Tetrahedron Lett. 25 1984 3293
19. R.B. Sykes, C.M. Cimarusti, D.P. Bonner, K. Bush, D.M. Floyd, N.H. Georgopapadakou, W.H. Koster, W.C. Liu, W.L. Parker, P.A. Principe, M.L. Rathnum, W.A. Slusarchyk, W.H. Trejo, and J.S. Welles Nature 291 1981 489
20. A. Imada, K. Kitano, K. Kitanka, M. Muroi, and M. Asai Nature 289 1981 590
21. C.M. Cimarusti, D.P. Bonner, H. Breuer, H.W. Chang, A.W. Fritz, D.M. Floyd, T.P. Kissick, K.H. Koster, D. Kronenthal, F. Massa, R.H. Mueller, J. Pluscec, W.A. Slusarchyk, R.B. Sykes, M. Taylor, and E.R. Weaver Tetrahedron 39 1983 2577
22. D.M. Floyd, A.W. Fritz, and C.M. Cimarusti J. Org. Chem. 47 1982 176
23. C.M. Cimarusti, H.E. Applegate, H.W. Chang, D.M. Floyd, W.H. Koster, W.A. Slusarchyk, and M.G. Young J. Org. Chem. 47 1982 179
24. H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem., Int. Ed. 2001 2004 40
25. H.C. Kolb, and K.B. Sharpless Drug Discovery Today 8 2003 1128
26. S.G. Agalave, S.R. Maujan, and V.S. Pore Chem. Asian J. 6 2011 2696
27. S. Afonin, R.W. Glaser, M. Berditchevskaja, P. Wadhwani, K.H. Guhrs, U. Mollmann, A. Perner, and A.S. Ulrich ChemBioChem 4 2003 1151
28. Murray P.R. Murray, E.J. Baron, M.A. Pfaller, F.C. Tenover, R.H. Yolken, Manual of Clinical Microbiology 7th ed. 1999 American Society for Microbiology Washington, DC
29. S.G. Waley Biochem. J. 205 1982 631