Synthesis and antibacterial activity of novel oxazolidinones bearing N-hydroxyacetamidine substituent

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 9, 2006, Pages 2391-2395

  Takhi, Mohamed ^a   Murugan, C ^a   Munikumar, M ^a   Bhaskarreddy, K M ^a   Singh, Gurpreet ^a   Sreenivas, K ^a   Sitaramkumar, M ^a   Selvakumar, N ^a   Das, J ^a   Trehan, Sanjay ^a   Iqbal, Javed ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

Author keywords

Acetamidine; Antibacterial; Linezolid; Oxazolidinone

Indexed keywords

ACETAMIDINE DERIVATIVE; CARBONYL DERIVATIVE; EPEREZOLID; LINEZOLID; N HYDROXYACETAMIDINE; OXAZOLIDINONE DERIVATIVE; THIOACETAMIDE; THIOCARBAMIC ACID; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DOSE RESPONSE; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN;

ANIMALS; ANTI-BACTERIAL AGENTS; DISEASE MODELS, ANIMAL; GRAM-NEGATIVE BACTERIA; GRAM-NEGATIVE BACTERIAL INFECTIONS; GRAM-POSITIVE BACTERIA; GRAM-POSITIVE BACTERIAL INFECTIONS; HYDROXAMIC ACIDS; MICE; MICROBIAL SENSITIVITY TESTS; MOLECULAR CONFORMATION; OXAZOLIDINONES; STEREOISOMERISM;

ANIMALIA; NEGIBACTERIA; POSIBACTERIA;

EID: 33644989449     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.01.109     Document Type: Article

References (31)

1. G.A. Ayliffe Clin. Infect. Dis. 24 Suppl. 1 1997 S74
2. R. Leclercq Clin. Infect. Dis. 24 Suppl. 1 1997 S80
3. C. Thornsberry, P.T. Ogilvie, H.P. Holley Jr., and D.F. Sahm Antimicrob. Agents Chemother. 43 1999 2612
4. M.A. Pfaller, K. Kugler, J. Freeman, and R.N. Jones Clin. Infect. Dis. 27 Suppl. 1 1998 764
5. M.A. Pfaller, R.N. Jones, G.V. Doern, H.S. Sader, K.C. Kugler, and M.L. Beach Diagn. Microbiol. Infect. Dis. 33 1999 283
6. P. Abi-Hanna, A.L. Frank, J.P. Quinn, S. Kelkar, P.C. Schreck-enberger, M.K. Hayden, and J.F. Marcinak Clin. Infect. Dis. 30 2000 630
7. P. Collignon J. Infect. Dis. 179 1999 1592
8. J. Merlino, M. Leroi, R. Bradbury, D. Veal, and C. Harbour J. Clin. Microbiol. 38 2000 2378
9. B.D. Cookson Infect. Control Hosp. Epidemiol. 21 2000 398
10. D. Clemett, and A. Markham Drug 59 2000 815
11. M.B. Gravestock, G.A. David, M.J. Betts, M. Dennis, G. Hatter, A. McGregor, M.L. Swain, R.G. Wilson, L. Woods, and A. Wookey Bioorg. Med. Chem. Lett. 13 2003 4179
12. O.A. Philips, E.E. Udo, A.A.M. Ali, and S.M. Samuel Bioorg. Med. Chem. 13 2005 4113
13. S.Y. Jang, Y.H. Ha, S.W. Ko, W. Lee, J. Lee, S. Kim, Y.W. Kim, W.K. Lee, and H.J. Ha Bioorg. Med. Chem. Lett. 12 2004 3881
14. C.S. Lee, D.A. Allwine, M.R. Barbachyn, K.C. Grega, L.A. Dolak, C.W. Ford, R.M. Jensen, E.P. Seest, J.C. Hamel, R.D. Schaadt, D. Stapert, B.H. Yagi, G.E. Zurenko, and M.J. Genin Bioorg. Med. Chem. 9 2001 3243
15. R. Griera, C.C. Llopart, M. Amat, J. Bosch, J.C.D. Castilo, and J. Huguet Bioorg. Med. Chem. Lett. 15 2005 2515
16. D.L. Shinabarger, K.R. Marotti, R.W. Murray, A.H. Lin, E.P. Melchoir, S.M. Swaney, D.S. Dunyak, W.F. Demyan, and J.M. Buysse Antimicrob. Agents Chemother. 41 1997 2132
17. P. Kloss, L. Xiong, A.S. Mankin, D.L. Shinabarger, and A.S. Mankin J. Mol. Biol. 294 1999 93
18. S. Tsirodas, H.S. Gold, G. Sakoulas, G.M. Eliopoulas, C. Wennerstein, L. Venkataraman, R.C. Moellering Jr., and M.J. Ferro Lancet 358 2001 207
19. A.P. Johnson, L. Tysall, M.W. Stockdale, N. Woodford, M.E. Kaufmann, M. Warner, D.M. Livermoore, F. Asboth, and F.J. Alleberger Eur. J. Clin. Microbial. Infect. Dis. 21 2002 751
20. N. Selvakumar, D. Srinivas, M.K. Khera, M.S. Kumar, R.N.V.S. Mamidi, H. Sarnaik, C. Charavaryamath, B.S. Rao, M.A. Raheem, J. Das, J. Iqbal, and R. Rajagopalan J. Med. Chem. 45 2002 3953
21. J. Das, C.V.L. Rao, T.V.R.S. Sastry, M. Roshiah, P.G. Sankar, A. Khadeer, M.S. Kumar, A. Mallik, N. Selvakumar, J. Iqbal, and S. Trehan Bioorg. Med. Chem. Lett. 15 2005 337
22. N. Selvakumar, M.A. Raheem, M.K. Khera, T.V. Rajale, M.S. Kumar, S. Kandepu, J. Das, R. Rajagopalan, J. Iqbal, and S. Trehan Bioorg. Med. Chem. Lett. 13 2003 4169
23. Solubility of compound 9a in MQ water was determined by UV-spectrophotometry method at 25°C after 4 h shaking. The water solubility of 9a was found to be 5.07 mg/mL, whereas the solubility of Linezolid is 3.06 mg/mL under the same conditions.
24. Hutchinson, D. K.; Brickner, S. J.; Barbachyn, M. R.; Gammill, R. B. PCT Int. Appl. WO 93/23384.
25. -1; MS: (m/z) 453 (M+1).
26. National Committee for Clinical Laboratory Standards. Methods for dilution antimicrobial-susceptibility tests for bacteria that grow aerobically. Approved Standard, 5th ed.; NCCLS: USA, 2000; M7-A5, Vol. 20, No. 2.
27. R. Tokuyama, Y. Takahashi, Y. Tomita, M. Tsubochi, T. Yoshida, N. Iwasaki, N. Kado, E. Okezaki, and O. Nagata Chem. Pharm. Bull. 49 2001 353
28. R. Tokuyama, Y. Takahashi, Y. Tomita, M. Tsubochi, N. Iwasaki, N. Kado, E. Okezaki, and O. Nagata Chem. Pharm. Bull. 49 2001 361
29. R. Tokuyama, Y. Takahashi, Y. Tomita, T. Suzuki, T. Yoshida, N. Iwasaki, N. Kado, E. Okezaki, and O. Nagata Chem. Pharm. Bull. 49 2001 347
30. F.L. Ciske, M. Barbachyn, M.J. Genin, K.C. Grega, C.S. Lee, L.A. Dolak, E.P. Seest, W. Watt, W.J. Adams, J.M. Friis, C.W. Ford, and G.E. Zurenko Bioorg. Med. Chem. Lett. 13 2003 4235
31. L.M. Thomasco, R.C. Gadwood, E.A. Weaver, J.M. Ochoada, C.W. Ford, G.E. Zurenko, J.C. Hamel, D. Stapert, J.K. Moerman, R.D. Schaadt, and B.H. Yagi Bioorg. Med. Chem. Lett. 13 2003 4193