Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis and in vitro Activity of Novel 1β-Methylcarbapenems Having Spiro[2,4]heptane Moieties. Part II

  • Park, Hyeong-Beom (Biomaterials Research Center, Korea Institute of Science and Technology) ;
  • Jung, Myung-Ho (Biomaterials Research Center, Korea Institute of Science and Technology) ;
  • Cho, Jung-Hyuck (Biomaterials Research Center, Korea Institute of Science and Technology) ;
  • Oh, Chang-Hyun (Biomaterials Research Center, Korea Institute of Science and Technology)
  • Published : 2008.08.20
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Abstract

The synthesis of a new series of 1$\beta$-methylcarbapenems having spiro[2,4]heptane moieties is described. Their in vitro antibacterial activities against both Gram-positive and Gram-negative bacteria were tested and the effect of substituents at the pyrrolidine ring was investigated. Most of the compounds were found to be more active compared to imipenem against Gram-negative bacteria. A particular compound (IIIc) having 7-oxo-5- azaspiro[2,4]heptane moiety showed the most potent antibacterial activity.

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References

  1. Leanza, W.; Wildonger, K.; 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.; 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.; Baker, F. L.; Christensen, B. G. Tetrahedron Lett. 1985, 26, 587 https://doi.org/10.1016/S0040-4039(00)89154-6
  7. Sato, M.; Takemura, M.; Atarashi, S.; Higashi, K.; Nagahara, T.; Furukawa, M.; Ikeuchi, T.; Osada, Y. J. Antibiot. 1987, 40, 1292 https://doi.org/10.7164/antibiotics.40.1292
  8. Oh, C.-H.; Cho, J.-H. J. Antibiot. 1994, 47, 126 https://doi.org/10.7164/antibiotics.47.126
  9. 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
  10. Oh, C.-H.; Cho, H.-W.; Lee, I.-K.; Gong, J.-Y.; Choi, J.-H.; Cho, J.-H. Arch. Pharm. Pharm. Med. Chem. 2002, 335, 152 https://doi.org/10.1002/1521-4184(200204)335:4<152::AID-ARDP152>3.0.CO;2-B
  11. Oh, C.-H.; Dong, H.-G.; Cho, H.-W.; Park, S. J.; Hong, J. H.; Cho, J.-H. Arch. Pharm. Pharm. Med. Chem. 2002, 335, 200 https://doi.org/10.1002/1521-4184(200205)335:5<200::AID-ARDP200>3.0.CO;2-X
  12. 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
  13. Iso, Y.; Irie, T.; Nishino, Y.; Motokawa, K.; Nishitani, Y. J. Antibiot. 1996, 49, 199 https://doi.org/10.7164/antibiotics.49.199
  14. Inoue, K.; Hamana, Y.; Inoue, T.; Fukasawa, M.; Kato, M. Abstracts of Papers of 34th Intersci. Conf. on Antimicro. Agents Chemother., No. 1, Orlando, 1994
  15. Sato, N.; Ohba, F. Drugs of Future 1996, 21, 361 https://doi.org/10.1358/dof.1996.021.04.353125
  16. Nada, J. Cur. Opin. Invest. Drugs 2000, 1(1), 31
  17. Youichi, K.; Shohgo, A.; Katsuhiro, K.; Kenichi, S.; Isao, H. J. Med. Chem. 1994, 37(20), 3344 https://doi.org/10.1021/jm00046a019
  18. Oh, C.-H.; Park, H. B.; Cho, J.-H. Archive der Pharmazie 2007, 340, 530 https://doi.org/10.1002/ardp.200700060
  19. Oh, C.-H.; Cho, H.-W.; Cho, J.-H. Eur. J. Med. Chem. 2006, 41, 825 https://doi.org/10.1016/j.ejmech.2006.02.006

Cited by

  1. ChemInform Abstract: Synthesis and in vitro Activity of Novel 1β-Methylcarbapenems Having Spiro[2,4]heptane Moieties. Part 2. vol.40, pp.6, 2009, https://doi.org/10.1002/chin.200906209