Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis and Antibacterial Activity of 1β-Methyl-2-[5-(1,2-disubstituted ethyl)-pyrrolidin-3-ylthio]carbapenem Derivatives. Part III

  • Cho, Jung-Hyuck (Medicinal Chemistry Research Center, Korea Institute of Science and Technology) ;
  • Ahn, Soo-Hyun (Medicinal Chemistry Research Center, Korea Institute of Science and Technology) ;
  • Jeon, Hee-chol (Medicinal Chemistry Research Center, Korea Institute of Science and Technology) ;
  • Kim, So-Young (Medicinal Chemistry Research Center, Korea Institute of Science and Technology) ;
  • Oh, Chang-Hyun (Medicinal Chemistry Research Center, Korea Institute of Science and Technology)
  • Published : 2006.05.20
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Abstract

The synthesis of a new series of 1 $\beta$-methylcarbapenems having 5-(1,2-disubstituted ethyl)pyrrolidine moiety are described. Their in vitro antibacterial activities against both Gram-positive and Gram-negative bacteria were tested and the effect of substituents on the pyrrolidine ring was investigated. Among them, compound (IIIc) having 1-methoxyimino-2-hydroxyethyl moiety showed the most potent antibacterial activity.

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References

  1. Leanza, W. J.; Wildonger, K. J.; Miller, T. W.; Christensen, B. G.J. Med. Chem. 1979, 22, 1435 https://doi.org/10.1021/jm00198a001
  2. Birnbaum, J.; Kahan, F. M.; MacDonald, J. S. Am. J. Med. 1985, 78(Suppl. 6A), 3
  3. Sunagawa, M.; Matsumure, H.; Inoue, T.; Fukasawa, M.; Kato,M. J. Antibiot.1990, 43, 519 https://doi.org/10.7164/antibiotics.43.519
  4. Gill, C. J.; Jackson, J. J.; Gerckens, L. S.; Pelak, B. A.; Thompson,R. K.; Sundelof, J. G.; Kropp, H.; Rosen, H. Antimicrob Agents Chemother. 1998, 42, 1996
  5. Shih, D. H.; Baker, F. L.; Christensen, B. G. Heterocycles 1984, 21, 29 https://doi.org/10.3987/S-1984-01-0029
  6. Shih, D. H.; Christensen, B. G. Tetrahedron Lett. 1985, 26, 587 https://doi.org/10.1016/S0040-4039(00)89154-6
  7. Sato, N.; Takemura, M.; Atarashi, S.; Higashi, K.; Nagahara, T.;Furukawa, M.; Ikeuchi, M.; Osada, Y. J. Antibiot.1987, 40,1292 https://doi.org/10.7164/antibiotics.40.1292
  8. Iso, Y.; Irie, T.; Nishino, Y.; Motokawa, K.; Nishitani, Y. J. Antibiot.1996, 49,199 https://doi.org/10.7164/antibiotics.49.199
  9. Inoue, K.; Hamana, Y.; Inoue, T.; Fukasawa, M.; Kato, M.Abstracts of Papers of 34th Intersci. Conf. on Antimicro. AgentsChemother.No. 1, Orlando, 1994
  10. Sato, N.; Ohba, F. Drugs Future 1996, 21, 361
  11. Oh, C.-H.; Cho, J.-H. J. Antibiot.1994, 47, 126 https://doi.org/10.7164/antibiotics.47.126
  12. Jin, C. B.; Jung, I. S.; Ku, H.-J.; Yook, J. W.; Kim, D.-H.; Cho, J.-H.; Kim, M. S.; Oh, C.-H. Toxicology 1999, 138, 59 https://doi.org/10.1016/S0300-483X(99)00078-5
  13. Oh, C. H.; Cho, H. W.; Cho, J. H. Eur. J. Med. Chem. 2002, 37, 743 https://doi.org/10.1016/S0223-5234(02)01397-1
  14. Oh, C. H.; Lee, S. C.; Cho, J. H. Eur. J. Med. Chem. 2003, 38,751 https://doi.org/10.1016/S0223-5234(03)00116-8
  15. Oh, C. H.; Cho, J. H. Eur. J. Med. Chem. in press

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  2. Synthesis and Antibacterial Activity of 1β-Methyl-2-[5-(1,2-disubstituted ethyl)pyrrolidin-3-ylthio]carbapenem Derivatives. Part 3. vol.38, pp.1, 2007, https://doi.org/10.1002/chin.200701215