Preparation, antibacterial evaluation and preliminary structure-activity relationship (SAR) study of benzothiazol- and benzoxazol-2-amine derivatives

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 9, 2012, Pages 3044-3049

  Ouyang, Liang ^a   Huang, Yuhui ^b   Zhao, Yuwei ^a   He, Gu ^a   Xie, Yongmei ^a   Liu, Jie ^a   He, Jun ^a   Liu, Bo ^a   Wei, Yuquan ^a  

^a SICHUAN UNIVERSITY   (China)

^b CHENGDU UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

Author keywords

Antibacterial; Benzothiazole; Benzoxazole; Methionyl tRNA synthetase inhibitors

Indexed keywords

AMPICILLIN; BENZOTHIAZOLE DERIVATIVE; BENZOXAZOLE DERIVATIVE; CEFOTAXIME; METHIONINE TRANSFER RNA LIGASE; SB 299683; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY TEST; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; GRAM POSITIVE BACTERIUM; HUMAN; HUMAN CELL; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR DOCKING; NONHUMAN; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION;

AMINES; ANTI-BACTERIAL AGENTS; BENZOTHIAZOLES; BENZOXAZOLES; METHIONINE-TRNA LIGASE; MICROBIAL SENSITIVITY TESTS; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP;

POSIBACTERIA; STAPHYLOCOCCUS AUREUS;

EID: 84859810320     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.03.079     Document Type: Article

References (35)

1. T.R. Walsh, J. Weeks, D.M. Livermore, and M.A. Toleman Lancet Infect. Dis. 11 2011 355
2. S.J. Dancer J. Hosp. Infect. 73 2009 378
3. K.J. Simmons, I. Chopra, and C.W.G. Fishwick Nat. Rev. Microbiol. 8 2010 501
4. U.A. Ochsner, X. Sun, T. Jarvis, I. Critchley, and N. Janjic Expert Opin. Investig. Drugs 16 2007 573
5. B.D. Bax, P.F. Chan, D.S. Eggleston, A. Fosberry, D.R. Gentry, F. Gorrec, I. Giordano, M.M. Hann, A. Hennessy, M. Hibbs, J.Z. Huang, E. Jones, J. Jones, K.K. Brown, C.J. Lewis, E.W. May, M.R. Saunders, O. Singh, C.E. Spitzfaden, C. Shen, A. Shillings, A.J. Theobald, A. Wohlkonig, N.D. Pearson, and M.N. Gwynn Nature 466 2010 935
6. D.J. Haydon, N.R. Stokes, R. Ure, G. Galbraith, J.M. Bennett, D.R. Brown, P.J. Baker, V.V. Barynin, D.W. Rice, S.E. Sedelnikova, J.R. Heal, J.M. Sheridan, S.T. Aiwale, P.K. Chauhan, A. Srivastava, A. Taneja, I. Collins, J. Errington, and L.G. Czaplewski Science 321 2008 1673
7. K. Kumar, D. Awasthi, S.Y. Lee, I. Zanardi, B. Ruzsicska, S. Knudson, P.J. Tonge, R.A. Slayden, and I. Ojima J. Med. Chem. 54 2011 374
8. P. Van de Vijver, G.H.M. Vondenhoff, S. Denivelle, J. Rozenski, J. Verhaegen, A. Van Aerschot, and P. Herdewijn Bioorg. Med. Chem. 17 2009 260
9. Y.Y. Zhang, and C.H. Zhou Bioorg. Med. Chem. Lett. 21 2011 4349
10. S. Alper-Hayta, M. Arisoy, O. Temiz-Arpaci, I. Yildiz, E. Aki, S. Ozkan, and F. Kaynak Eur. J. Med. Chem. 43 2008 2568
11. T. Ertan, I. Yildiz, B. Tekiner-Gulbas, K. Bolelli, O. Temiz-Arpaci, S. Ozkan, F. Kaynak, I. Yalcin, and E. Aki Eur. J. Med. Chem. 44 2009 501
12. O. Temiz-Arpaci, I. Yildiz, S. Ozkan, F. Kaynak, E. Aki-Sener, and I. Yalcin Eur. J. Med. Chem. 43 2008 1423
13. I. Yildiz-Oren, I. Yalcin, E. Aki-Sener, and N. Ucarturk Eur. J. Med. Chem. 39 2004 291
14. T.I. Moy, A.L. Conery, J. Larkins-Ford, G. Wu, R. Mazitschek, G. Casadei, K. Lewis, A.E. Carpenter, and F.M. Ausubel ACS Chem. Biol. 4 2009 527
15. S. Braun, A. Botzki, S. Salmen, C. Textor, G. Bernhardt, S. Dove, and A. Buschauer Eur. J. Med. Chem. 46 2011 4419
16. R.L. Jarvest, J.M. Berge, V. Berry, H.F. Boyd, M.J. Brown, J.S. Elder, A.K. Forrest, A.P. Fosberry, D.R. Gentry, M.J. Hibbs, D.D. Jaworski, P.J. O'Hanlon, A.J. Pope, S. Rittenhouse, R.J. Sheppard, C. Slater-Radosti, and A. Worby J. Med. Chem. 2002 1959 45
17. U.A. Ochsner, C.L. Young, M.C. Stone, F.B. Dean, N. Janjic, and I.A. Critchley Antimicrob. Agents Chemother. 49 2005 4253
18. I.A. Critchley, C.L. Young, K.C. Stone, U.A. Ochsner, J. Guiles, T. Tarasow, and N. Janjic Antimicrob. Agents Chemother. 49 2005 4247
19. R.L. Jarvest, J.M. Berge, M.J. Brown, P. Brown, J.S. Elder, A.K. Forrest, C.S.V. Houge-Frydrych, P.J. O'Hanlon, D.J. McNair, S. Rittenhouse, and R.J. Sheppard Bioorg. Med. Chem. Lett. 13 2003 665
20. R.L. Jarvest, S.G. Erskine, A.K. Forrest, A.P. Fosberry, M.J. Hibbs, J.J. Jones, P.J. O'Hanlon, R.J. Sheppard, and A. Worby Bioorg. Med. Chem. Lett. 15 2005 2305
21. S.Y. Kim, and J. Lee Bioorg. Med. Chem. 11 2003 5325
22. S.Y. Kim, Y.S. Lee, T. Kang, S. Kim, and J. Lee Bioorg. Med. Chem. Lett. 16 2006 4898
23. Farhanullah, S.Y. Kim, E.J. Yoon, E.C. Choi, S. Kim, T. Kang, F. Samrin, S. Puri, and J. Lee Bioorg. Med. Chem. 14 2006 7154
24. R. Farhanullah, T. Kang, E.J. Yoon, E.C. Choi, S. Kim, and J. Lee Eur. J. Med. Chem. 44 2009 239
25. N. Bharatham, K. BlIaratham, and K.W. Lee J. Mol. Graph. Model. 25 2007 813
26. J. Finn, M. Stidham, M. Hilgers, and G.C. Kedar Bioorg. Med. Chem. Lett. 18 2008 3932
27. J.B. Li, L. Xia, B. Wu, T. Wang, and Z.Z. Jiang Chin. Chem. Lett. 19 2008 1193
28. S.R. Byeon, Y.J. Jin, S.J. Lim, J.H. Lee, K.H. Yoo, K.J. Shin, S.J. Oh, and D.J. Kim Bioorg. Med. Chem. Lett. 17 2007 4022
29. S. Saeed, N. Rashid, P.G. Jones, M. Ali, and R. Hussain Eur. J. Med. Chem. 45 2010 1323
30. P. Bandyopadhyay, M. Sathe, S. Ponmariappan, A. Sharma, P. Sharma, A.K. Srivastava, and M.P. Kaushik Bioorg. Med. Chem. Lett. 21 2011 7306
31. E. Al-Moubarak, and C. Simons J. Mol. Model. 17 2011 1679
32. Z.M. Qian, S.J. Qin, L. Yi, H.J. Li, P. Li, and X.D. Wen Biomed. Chromatogr. 22 2008 202
33. M. Sharma, P. Joshi, N. Kumar, S. Joshi, R.K. Rohilla, N. Roy, and D.S. Rawat Eur. J. Med. Chem. 46 2011 480
34. K. Nakanishi, Y. Ogiso, T. Nakama, S. Fukai, and O. Nureki Nat. Struct. Mol. Biol. 12 2005 931
35. E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng, and T.E. Ferrin J. Comput. Chem. 25 2004 1605