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http://dx.doi.org/10.5012/bkcs.2008.29.8.1472

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)
Publication Information
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.
Keywords
1β -Methylcarbapenems; Antibacterial activity; Spiro[2,4]heptane; Substituent effects
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1 Shih, D. H.; Baker, F. L.; Christensen, B. G. Tetrahedron Lett. 1985, 26, 587   DOI   ScienceOn
2 Leanza, W.; Wildonger, K.; Miller, T. W.; Christensen, B. G. J. Med. Chem. 1979, 22, 1435   DOI
3 Birnbaum, J.; Kahan, F. M.; MacDonald, J. S. Am. J. Med. 1985, 78, (Suppl. 6A), 3
4 Sunagawa, M.; Matsumure, H.; Inoue, T.; Kato, M. J. Antibiot. 1990, 43, 519   DOI
5 Shih, D. H.; Baker, F. L.; Christensen, B. G. Heterocycles 1984, 21, 29   DOI
6 Sato, M.; Takemura, M.; Atarashi, S.; Higashi, K.; Nagahara, T.; Furukawa, M.; Ikeuchi, T.; Osada, Y. J. Antibiot. 1987, 40, 1292   DOI
7 Oh, C.-H.; Cho, H.-W.; Cho, J.-H. Eur. J. Med. Chem. 2002, 37, 743   DOI   ScienceOn
8 Iso, Y.; Irie, T.; Nishino, Y.; Motokawa, K.; Nishitani, Y. J. Antibiot. 1996, 49, 199   DOI   ScienceOn
9 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   DOI   ScienceOn
10 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   DOI   ScienceOn
11 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   DOI   ScienceOn
12 Nada, J. Cur. Opin. Invest. Drugs 2000, 1(1), 31
13 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
14 Sato, N.; Ohba, F. Drugs of Future 1996, 21, 361   DOI
15 Youichi, K.; Shohgo, A.; Katsuhiro, K.; Kenichi, S.; Isao, H. J. Med. Chem. 1994, 37(20), 3344   DOI   ScienceOn
16 Oh, C.-H.; Cho, H.-W.; Cho, J.-H. Eur. J. Med. Chem. 2006, 41, 825   DOI   ScienceOn
17 Oh, C.-H.; Park, H. B.; Cho, J.-H. Archive der Pharmazie 2007, 340, 530   DOI   ScienceOn
18 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
19 Oh, C.-H.; Cho, J.-H. J. Antibiot. 1994, 47, 126   DOI   ScienceOn