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Synthesis and Antibacterial Activity of Novel 2-Oxo-pyrrolidinyl Oxazolidinones

  • Bhattarai, Deepak (Center for Neuro-Medicine, Brain Science Institute, Korea Institute of Science and Technology) ;
  • Lee, Sun-Hee (Center for Neuro-Medicine, Brain Science Institute, Korea Institute of Science and Technology) ;
  • Kim, Hyeong-Kyu (Center for Neuro-Medicine, Brain Science Institute, Korea Institute of Science and Technology) ;
  • Kang, Soon-Bang (Center for Neuro-Medicine, Brain Science Institute, Korea Institute of Science and Technology) ;
  • Pae, Ae-Nim (Center for Neuro-Medicine, Brain Science Institute, Korea Institute of Science and Technology) ;
  • Kim, Eunice Eun-Kyeong (Center for Neuro-Medicine, Brain Science Institute, Korea Institute of Science and Technology) ;
  • Oh, Taeg-Won (Department of Microbiology and the Brain Korea 21 Project for the Medical Sciences, Yonsei University College of Medicine) ;
  • Cho, Sang-Nae (Department of Microbiology and the Brain Korea 21 Project for the Medical Sciences, Yonsei University College of Medicine) ;
  • Keum, Gyo-Chang (Center for Neuro-Medicine, Brain Science Institute, Korea Institute of Science and Technology)
  • Received : 2012.01.25
  • Accepted : 2012.01.30
  • Published : 2012.04.20

Abstract

Novel antibacterial oxazolidinones bearing pyrrolidinone ring system at the C-5 side chain were synthesized and their in vitro antibacterial activities were evaluated. Most of the synthesized oxazolidinones showed good antibacterial activity against the Gram-positive and Gram-negative bacteria tested.

Keywords

References

  1. Spellberg, B.; Guidos, R.; Gilbert, D.; Bradley, J.; Boucher, H. W.; Scheld, W. M.; Barlett, J. G.; Edwards, J., Jr. Clin. Infect. Dis. 2008, 46, 155-164. https://doi.org/10.1086/524891
  2. Styers, D.; Sheehan, D. J.; Hogan, P.; Sahm, D. F. Ann. Clin. Microbiol. Antimicrob. 2006, 5, 2. https://doi.org/10.1186/1476-0711-5-2
  3. Fernandes, P. Nature Biotech. 2006, 24, 1497-1503. https://doi.org/10.1038/nbt1206-1497
  4. Fukuda, Y. Drugs of the Future 2009, 34, 127-136. https://doi.org/10.1358/dof.2009.034.02.1313642
  5. Zurenko, G. E.; Gibson. J. K.; Shinabarger, D. L.; Aristoff, P. A.; Ford, C. W.; Tarpley, W. G. Curr. Opin. Pharmacol. 2001, 1, 470- 476. https://doi.org/10.1016/S1471-4892(01)00082-0
  6. Brickner, S. J.; Barbachyn, M. R.; Hutchinson, D. K.; Manninen, P. R. J. Med. Chem. 2008, 51, 1981-1990. https://doi.org/10.1021/jm800038g
  7. Dotis, J.; Iosifidis, E.; Ioannidou, M.; Roilides, E. Int. J. Infect. Dis. 2010, 14, e638-e648. https://doi.org/10.1016/j.ijid.2009.10.002
  8. Cynamon, M. H.; Klemens, S. P.; Sharpe, C. A.; Chase, S. Antimicrob. Agents Chemother. 1999, 43, 1189-1191.
  9. Williams, K. N.; Stover, C. K.; Zhu, T.; Tasneen, R.; Tyagi, S.; Grosset, J. H.; Nuermberger, E. Antimicrob. Agents Chemother. 2009, 53, 1314-1319. https://doi.org/10.1128/AAC.01182-08
  10. Anger, H. A.; Dworkin, F.; Sharma, S.; Munsiff, S. S.; Nilsen, D. M.; Ahuja, S. D. J. Antimicrob. Chemother. 2010, 65, 775-783. https://doi.org/10.1093/jac/dkq017
  11. Ippolito, J. A.; Kanyo, Z. F.; Wang, D.; Franceschi, F. J.; Moore, P. B.; Steitz, T. A.; Duffy, E. M. J. Med. Chem. 2008, 51, 3353-3356. https://doi.org/10.1021/jm800379d
  12. Jones, R. N.; Kohno, S.; Ono, Y.; Ross, J. E.; Yanagihara, K. Diagn. Microbiol. Infect. Dis. 2009, 64 191-204. https://doi.org/10.1016/j.diagmicrobio.2009.03.001
  13. Gracia, M. S.; De la Torre, M. A.; Morales, G.; Pelaez, B.; Tolon, M. J.; Domingo, S.; Candel, F. J.; Andrade, R.; Arribi, A.; Garcia, N.; Sagasti, F. M.; Fereres, J.; Picazo, J. J. Am. Med. Ass. 2010, 303, 2260-2264. https://doi.org/10.1001/jama.2010.757
  14. Meka, V. G.; Gold, H. S. Clin. Infect. Dis. 2004, 39, 1010-1015. https://doi.org/10.1086/423841
  15. Tsiodras, S.; Gold, H. S.; Sakoulas, G.; Eliopoulos, G. M.; Wennersten, C.; Venkataraman, Lata.; Moellering, R. C., Jr.; Ferraro, M. J. Lancet 2001, 358, 207-208. https://doi.org/10.1016/S0140-6736(01)05410-1
  16. Scheetz, M. H.; Knechtel, S. A.; Malczynski, M.; Postelnick, M. J.; Qi, C. Antimicrob. Agents Chemother. 2008, 52, 2256-2259. https://doi.org/10.1128/AAC.00070-08
  17. Trevino, M.; Martínez-Lamas, L.; Romero-Jung, P. A.; Giráldez, J. M.; Alvarez-Escudero, J.; Regueiro, B. J. Eur. J. Clin. Microbiol. Infect. Dis. 2009, 28, 527-533. https://doi.org/10.1007/s10096-008-0657-5
  18. McCusker, K. P.; Fujimori, D. G. ACS Chem. Biol. 2012, in press.
  19. Long, K. S.; Poehlsgaard, J.; Kehrenberg, C.; Schwarz, S.; Vester, B. Antimicrob. Agents Chemother. 2006, 50, 25002505.
  20. Morales, G.; Picazo, J. J.; Baos, E.; Candel, F. J.; Arribi, A.; Beatriz-Pelaez, B.; Andrade, R.; M.-A. de la Torre, Fereres, J.; Sanchez-Garc ia, M. Clin. Infect. Dis. 2010, 50, 821-825. https://doi.org/10.1086/650574
  21. Brickner, S. J.; Barbachyn, M. R.; Hutchinson, D. K.; Manninen, P. R. J. Med. Chem. 2008, 51, 1981-1990. https://doi.org/10.1021/jm800038g
  22. Renslo, A. R.; Luehr, G. W.; Gordeev, M. F. Bioorg. Med. Chem. 2006, 14, 4227-4240. https://doi.org/10.1016/j.bmc.2006.01.068
  23. Prasad, J. V. Curr. Opin. Microbiol. 2007, 10, 454-460. https://doi.org/10.1016/j.mib.2007.08.001
  24. Poce, G.; Zappia, G.; Porretta, G. C.; Botta, B.; Biava, M. Expert Opin. Ther. Patents 2008, 18, 97-121. https://doi.org/10.1517/13543776.18.2.97
  25. Das, B.; Rajarao, A. V. S.; Rudra, S.; Yadav, A.; Ray, A.; Pandya, M.; Ashok Rattan, A.; Mehta, A. Bioorg. Med. Chem. Lett. 2009, 19, 6424-6428. https://doi.org/10.1016/j.bmcl.2009.09.054
  26. Prokocimer, P.; Bien, P.; Surber, J.; Mehra, P.; DeAnda, C.; Bulitta, J. B.; Corey, G. R. Antimicrob. Agents Chemother. 2011, 55, 583-592. https://doi.org/10.1128/AAC.00076-10
  27. Lemaire, S.; Kosowska-Shick, K.; Appelbaum, P. C.; Verween, G.; Tulkens, P. M.; Van Bambeke, F. Antimicrob. Agents Chemother. 2010, 54, 2549-2559. https://doi.org/10.1128/AAC.01724-09
  28. Gordeev, M. F.; Yuan, Z.; Liu, J. WO 2008108988, 2008, CAN 149:355886.
  29. Paget, S. D.; Foleno, B. D.; Boggs, C. M.; Goldschmidt, R. M.; Hlasta, D. J.; Weidner-Wells, M. A.; Werblood, H. M.; Wira, E.; Bush, K.; Macielag, M. J. Bioorg. Med. Chem. Lett. 2003, 13, 4173-4177. https://doi.org/10.1016/j.bmcl.2003.08.031
  30. Roehrig, S.; Straub, A.; Pohlmann, J.; Lampe, T.; Pernerstorfer, J.; Schlemmer, K.-H.; Reinemer, P.; Perzborn, E. J. Med. Chem. 2005, 48, 5900-5908. https://doi.org/10.1021/jm050101d
  31. Clinical and Laboratory Standards Institute. Performance standards for antimicrobial susceptibility testing. 15th informational supplement. M100-S15. Wine, PA: CLSI; 2005.
  32. Collins, L. A.; Franzblau, S. G. Antimicrob. Agents Chemother. 1997, 41, 1004-1009.
  33. Genin, M. J.; Hutchinson, D. K.; Allwine, D. A.; Hester, J. B.; Emmert, D. E.; Garmon, S. A.; Ford, C. W.; Zurenko, G. E.; Hamel, J. C.; Schaadt, R. D.; Stapert, D.; Yagi, B. H.; Friis, J. M.; Shobe, E. M.; Adams, W. J. J. Med. Chem. 1998, 41, 5144-5147. https://doi.org/10.1021/jm980546k
  34. Kang, J.-H.; Park, C.-H.; Kwon, J.-S. WO 2005042523, 2005, CAN 142:463731.

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