New linezolid-like 1,2,4-oxadiazolesactive against Gram-positive multiresistant pathogens

European Journal of Medicinal Chemistry

Volumn 65, Issue , 2013, Pages 533-545

  Fortuna, Cosimo G ^a   Bonaccorso, Carmela ^a   Bulbarelli, Alessandra ^b   Caltabiano, Gianluigi ^c   Rizzi, Laura ^b   Goracci, Laura ^a   Musumarra, Giuseppe ^a   Pace, Andrea ^d,e   Piccionello, Antonio Palumbo ^d,e   Guarcello, Annalisa ^d,e   Pierro, Paola ^d,e   Cocuzza, Clementina E A ^b   Musumeci, Rosario ^b  

^a UNIVERSITY OF CATANIA   (Italy)

^b UNIVERSITY OF MILANO BICOCCA   (Italy)

^c UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^d UNIVERSITY OF PALERMO   (Italy)

^e Istituto Euro Mediterraneo di Scienza e Tecnologia IEMEST   (Italy)

Author keywords

Antimicrobial activity; Cell viability; Drug design; Linezolid; Oxazolidinones; Staphylococcus aureus

Indexed keywords

1,2,4 OXADIAZOLE DERIVATIVE; 3 METHYL 5 (2',4' DIFLUOROPHENYL) 1,2,4 OXADIAZOLE; 3 METHYL 5 (4' FLUOROPHENYL) 1,2,4 OXADIAZOLE; 3 [3' FLUORO 4' (3'' METHYL 1,2,4 OXADIAZOL 5 YL)PHENYL] 5 (AMINOMETHYL) OXAZOLIDIN 2 ONE; 3 [3' FLUORO 4' (3'' METHYL 1,2,4 OXADIAZOL 5 YL)PHENYL] 5 (AZIDOMETIL) OXAZOLIDIN 2 ONE; 3 [3' FLUORO 4' (3'' METHYL 1,2,4 OXADIAZOL 5 YL)PHENYL] 5 (N ACETYLAMINOMETHYL) OXAZOLIDIN 2 ONE; 3 [3' FLUORO 4' (3'' METHYL 1,2,4 OXADIAZOL 5 YL)PHENYL] 5 (N THIOACETYLAMINOMETHYL) OXAZOLIDIN 2 ONE; 3 [3' FLUORO 4' (3'' METHYL 1,2,4 OXADIAZOL 5 YL)PHENYL] 5 [(1,2,4 TRIAZOL 1 YL)METHYL]OXAZOLIDIN 2 ONE; 3 [3' FLUORO 4' (3'' METHYL 1,2,4 OXADIAZOL 5 YL)PHENYL] 5 [(IMIDAZOL 1 YL)METHYL]OXAZOLIDIN 2 ONE; 3 [3' FLUORO 4' (3'' METHYL 1,2,4 OXADIAZOL 5 YL)PHENYL] 5 [(PYRAZOL 1 YL)METHYL]OXAZOLIDIN 2 ONE; 3 [3' FLUORO 4' (3'' METHYL 1,2,4 OXADIAZOL 5'' YL)PHENYL] 5 (IODOMETHYL) OXAZOLIDIN 2 ONE; 3 [4' (3'' METHYL 1,2,4 OXADIAZOL 5 YL)PHENYL] 5 (AMINOMETHYL) OXAZOLIDIN 2 ONE; 3 [4' (3'' METHYL 1,2,4 OXADIAZOL 5 YL)PHENYL] 5 (N ACETYLAMINOMETHYL) OXAZOLIDIN 2 ONE; 3 [4' (3'' METHYL 1,2,4 OXADIAZOL 5 YL)PHENYL] 5 (N THIOACETYLAMINOMETHYLL) OXAZOLIDIN 2 ONE; 3 [4' (3'' METHYL 1,2,4 OXADIAZOL 5 YL)PHENYL] 5 [(1,2,4 TRIAZOL 1 YL)METHYL]OXAZOLIDIN 2 ONE; 3 [4' (3'' METHYL 1,2,4 OXADIAZOL 5 YL)PHENYL] 5 [(IMIDAZOL 1 YL)METHYL]OXAZOLIDIN 2 ONE; 3 [4' (3'' METHYL 1,2,4 OXADIAZOL 5 YL)PHENYL] 5 [(PYRAZOL 1 YL)METHYL]OXAZOLIDIN 2 ONE; 3 [4' (3'' METHYL 1,2,4 OXADIAZOL 5'' YL) PHENYL] 5 (IODOMETHYL) OXAZOLIDIN 2 ONE; LINEZOLID; N ALLYL 3 FLUORO 4 (3' METHYL 1,2,4 OXADIAZOL 5' YL)ANILINE; N ALLYL 4 (3' METHYL 1,2,4 OXADIAZOL 5' YL)ANILINE; TERT BUTYL N ALLYL [3 FLUORO 4 (3 METHYL 1,2,4 OXADIAZOL 5' YL)PHENYL]CARBAMATE; TERT BUTYL N ALLYL [4 (3' METHYL 1,2,4 OXADIAZOL 5' YL)PHENYL]CARBAMATE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DEINOCOCCUS RADIODURANS; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; GRAM POSITIVE BACTERIUM; IN VITRO STUDY; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; METHICILLIN SUSCEPTIBLE STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR INTERACTION; MOLECULAR MODEL; NONHUMAN; STRUCTURE ACTIVITY RELATION;

EID: 84879472813     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.03.069     Document Type: Article

References (64)

1. Infectious Diseases Society of America, The 10 x ′20 initiative: pursuing a global commitment to develop 10 new antibacterial drugs by 2020, Clin. Infect. Dis. 50 (2010) 2081-2083.
2. C. Zou, L. Zhou, Mol. Simul. 33 (2007) 517-530.
3. D.N. Wilson, F. Schluenzen, J.M. Harms, A.L. Starosta, S.R. Connell, P. Fucini, Proc. Natl. Acad. Sci. U. S. A. 105 (2008) 13339-13344.
4. J.A. Ippolito, Z.F. Kanyo, D. Wang, F.J. Franceschi, P.B. Moore, T.A. Steitz, E.M. Duffy, J. Med. Chem. 51 (2008) 3353-3356.
5. S. Tsiodras, H.S. Gold, G. Sakoulas, G.M. Eliopoulos, C. Wennersten, L. Venkataraman, R.C. Moellering, M.J. Ferraro, Lancet 358 (2001) 207-208.
6. C. Auckland, L. Teare, F. Cooke, M.E. Kaufmann, M. Warner, G. Jones, K. Bamford, H. Ayles, A.P. Johnson, J. Antimicrob. Chemother. 50 (2002) 743-746.
7. J. Seedat, G. Zick, I. Klare, C. Konstabel, N. Weiler, H. Sahly, Antimicrob. Agents Chemother. 50 (2006) 4217-4219.
8. S. Kelly, J. Collins, M. Maguire, C. Gowing, M. Flanagan, M. Donnelly, P.G. Murphy, J. Antimicrob. Chemother. 61 (2008) 901-907.
9. J.V.N. Vara Prasad, Curr. Opin. Microbiol. 10 (2007) 454-460.
10. D.K. Hutchinson, Curr. Top. Med. Chem. 3 (2003) 1021-1042.
11. M.B. Gravestock, Curr. Opin. Drug Discov. Dev. 8 (2005) 469-477.
12. M.R. Barbachyn, C.W. Ford, Angew. Chem. Int. Ed. 42 (2003) 2010-2023.
13. A.R. Renslo, G.W. Luehr, M.F. Gordeev, Bioorg. Med. Chem. 14 (2006) 4227-4240.
14. Y.W. Jo, W.B. Im, J.K. Rhee, M.J. Shim, W.B. Kim, E.C. Choi, Bioorg. Med. Chem. 12 (2004) 5909-5915.
15. C. Farrerons Gallemi, US Patent 2005/0014806, 2005.
16. L.B. Snyder, Z. Meng, R. Mate, S.V. D'Andrea, A. Marinier, et al., Bioorg. Med. Chem. Lett. 14 (2004) 4735-4739.
17. A. Palumbo Piccionello, R. Musumeci, C. Cocuzza, C.G. Fortuna, A. Guarcello, P. Pierro, A. Pace, Eur. J. Med. Chem. 50 (2012) 441-448.
18. F. Broccolo, G. Cainelli, G. Caltabiano, C.E.A. Cocuzza, C.G. Fortuna, P. Galletti, D. Giacomini, G. Musumarra, R. Musumeci, A. Quintavalla, J. Med. Chem. 49 (2006) 2804-2811.
19. M. Baroni, G. Cruciani, S. Sciabola, F. Perruccio, J.S. Mason, J. Chem. Inf. Model. 47 (2007) 279-294.
20. A. Pace, P. Pierro, Org. Biomol. Chem. 7 (2009) 4337-4348.
21. S. Buscemi, A. Pace, R. Calabrese, N. Vivona, P. Metrangolo, Tetrahedron 57 (2001) 5865-5871.
22. S. Buscemi, A. Pace, A. Palumbo Piccionello, I. Pibiri, N. Vivona, Heterocycles 63 (2004) 1619-1628.
23. A. Palumbo Piccionello, A. Pace, I. Pibiri, S. Buscemi, N. Vivona, Tetrahedron 62 (2006) 8792-8797.
24. A. Palumbo Piccionello, A. Pace, P. Pierro, I. Pibiri, S. Buscemi, N. Vivona, Tetrahedron 65 (2009) 119-127.
25. K.C. Grega, M.R. Barbachyn, S.J. Brickner, S.A. Mizsak, J. Org. Chem. 60 (1995) 5255-5261.
26. H. Biswajit Das, H. Sonali Rudra, A. Songita Songita, P. Mohammad Salman, H. Ashok Rattan, US Patent 2008/0188470, 2008.
27. J.B. Locke, J. Finn, M. Hilgers, G. Morales, S. Rahawi, G.C. Kedar, J.J. Picazo, W. Im, K.J. Shaw, J.L. Stein, Antimicrob. Agents Chemother. 54 (2010) 5337-5343.
28. O.A. Phillips, E.E. Udo, A.A. Ali, et al., Bioorg. Med. Chem. 35 (2003) 1156.
29. M.B. Gravestock, D.G. Acton, M.J. Betts, M. Dennis, G. Hatter, et al. 13 (2003) 4179.
30. L.M. Thomasco, E.A. Weaver, J.M. Ochoada, R.C. Gadwood, G.E. Zurenko, C.W. Ford, Abstr. Intersci. Conf. Antimicrob. Agents Chemother. Intersci. Conf. Antimicrob. Agents Chemother. 40 (2000) 216.
31. S.-Y. Yhang, et al., Bioorg. Med. Chem. Lett. 14 (2004) 3881-3883.
32. S.J. Brickner, Curr. Pharm. Des. 2 (1996) 175-194.
33. C.H. Park, J. Med. Chem. 35 (1992) 1156-1165.
34. M.R. Barbachyn, Adv. Exp. Med. Biol. 456 (1998) 219-238.
35. S. Besier, A. Ludwig, J. Zander, V. Brade, T.A. Wichelhaus, Antimicrob. Agents Chemother. 52 (2008) 1570-1572.
36. A. Liakopoulos, C. Neocleous, D. Klapsa, M. Kanellopoulou, I. Spiliopoulou, K.D. Mathiopoulos, E. Papafrangas, E. Petinaki, J. Antimicrob. Chemother. 64 (2009) 206-207.
37. J.L. Hansen, P.B. Moore, T.A. Steitz, J. Mol. Biol. 330 (2003) 1061-1075.
38. V. Meka, S.K. Pillai, G. Sakoulas, C. Wennersten, L. Venkataraman, P.C. DeGirolami, G.M. Eliopoulos, R.C. Moellering Jr., H.S. Gold, J. Infect. Dis. 190 (2004) 311-317.
39. D.M. Livermore, M. Warner, S. Mushtaq, S. North, N. Woodford, Antimicrob. Agents Chemother. 51 (2007) 1112-1114.
40. V.G. Meka, H.S. Gold, A. Cooke, L. Venkataraman, G.M. Eliopoulos, R.C. Moellering, S.G. Jenkins, J. Antimicrob. Chemother. 54 (2004) 818-820.
41. J.B. Locke, M. Hilgers, K.J. Shaw, Antimicrob. Agents Chemother. 53 (2009) 5275-5278.
42. F. Perruccio, J. Mason, S. Sciabola, M. Baroni, in: G. Cruciani (Ed.), Molecular Interaction Fields in Drug Discovery, Methods and Principles in Medicinal Chemistry, vol. 27, Wiley-VCH, Weinheim, 2005, pp. 83-102.
43. S. Cross, M. Baroni, E. Carosati, P. Benedetti, S. Clementi, J. Chem. Inf. Model. 50 (2010) 1442-1450.
44. P.J.A. Goodford, J. Med. Chem. 28 (1985) 849-857.
45. E. Carosati, S. Sciabola, G. Cruciani, J. Med. Chem. 47 (2004) 5114-5125.
46. The GRID Package, Version 22, is distributed from Molecular Discovery Ltd. http://www.moldiscovery.com.
47. E. Carosati, G. Cruciani, A. Chiarini, R. Budriesi, P. Ioan, R. Spisani, D. Spinelli, B. Cosimelli, F. Fusi, M. Frosini, R. Matucci, F. Gasparrini, A. Ciogli, P.J. Stephens, F.J. Devlin, J. Med. Chem. 49 (2006) 5206-5216.
48. E. Carosati, R. Mannhold, P. Wahl, J.B. Hansen, T. Fremming, I. Zamora, G. Cianchetta, M. Baroni, J. Med. Chem. 50 (2007) 2117-2126.
49. R. Budriesi, B. Cosimelli, P. Ioan, M.P. Ugenti, E. Carosati, M. Frosini, F. Fusi, R. Spisani, S. Saponara, G. Cruciani, E. Novellino, D. Spinelli, A. Chiarini, J. Med. Chem. 52 (2009) 2352-2362.
50. G. Muratore, L. Goracci, B. Mercorelli, A. Foeglein, P. Digard, G. Cruciani, G. Palù, A. Loregian, Proc. Natl. Acad. Sci. U. S. A. (2012), http://dx.doi.org/10.1073/pnas.1119817109. (Published ahead of print 02.04.12).
51. S. Sciabola, R. Stanton, J.E. Mills, M.M. Flocco, M. Baroni, G. Cruciani, F. Perruccio, J.S. Mason, J. Chem. Inf. Model. 50 (2010) 155-169.
52. S. Banala, R.D. Süssmuth, ChemBioChem 11 (2010) 1335.
53. Clinical and Laboratory Standards Institute. Approved Standard, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically, ninth ed., vol. 32, M07-A9, Wayne, Pennsylvania, 2011.
54. E.C. Pirtle, Am. J. Vet. Res. 27 (1966) 747-749.
55. D.P. Aden, A. Fogel, S. Plotkin, I. Damjanov, B.B. Knowles, Nature 282 (1979) 615-616.
56. G. Pozzi, M. Guidi, F. Laudicina, M. Marazzi, L. Falcone, R. Betti, C. Crosti, E. Müller, G.E. Di Mattia, V. Locatelli, A. Torsello, J. Endocrinol. Invest. 27 (2004) 142-149.
57. A. Bulbarelli, E. Lonati, E. Cazzaniga, M. Gregori, M. Masserini, Mol. Cell. Neurosci. 42 (2009) 75-80.
58. D.A. Case, T.E. Cheatham, T. Darden, H. Gohlke, R. Luo, K.M. Merz, A. Onufriev, C. Simmerling, B. Wang, R.J. Woods, J. Comput. Chem. 26 (2005) 1668-1688.
59. L.L.C. Schrodinger, The PyMOL Molecular Graphics System, Version 1.5r3 (2010).
60. M. Rother, K. Rother, T. Puton, J.M. Bujnicki, Nucleic Acids Res. 39 (2011) 4007-4022.
61. D.A. Case, T.A. Darden, T.E. Cheatham, C.L. Simmerling, J. Wang, R.E. Duke, R. Luo, M. Crowley, R.C. Walker, W. Zhang, K.M. Merz, B. Wang, S. Hayik, A. Roitberg, G. Seabra, I. Kolossvary, K.F. Wong, F. Paesani, J. Vanicek, X. Wu, S.R. Brozell, T. Steinbrecher, H. Gohlke, L. Yang, C. Tan, J. Mongan, V. Hornak, G. Cui, D.H. Mathews, M.G. Seetin, C. Sagui, V. Babin, P.A. Kollman, Amber 10, University of California, San Francisco, 2008.
62. Chemical Computing Group, Inc, 2011.
63. J. Wang, R.M. Wolf, J.W. Caldwell, P.A. Kollman, D.A. Case, J. Comput. Chem. 25 (2004) 1157-1174.
64. J.P. Brincat, E. Carosati, S. Sabatini, G. Manfroni, A. Fravolini, J.L. Raygada, D. Patel, G.W. Kaatz, G. Cruciani, J. Med. Chem. 54 (2011) 354-365.