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Antibacterial Activity of Naphthyridone Derivatives Containing 8-Alkoxyimino-1,6-dizaspiro[3,4]octane Scaffolds
Corresponding Author(s) : Mingliang Liu
Asian Journal of Chemistry,
Vol. 26 No. 13 (2014): Vol 26 Issue 13
Abstract
We report herein in vitro antibacterial activity of a series of novel naphthyridone derivatives containing 8-alkoxyimino-1,6-dizaspiro-[3.4]octane scaffolds, the position isomers of the side chain at the C-7 position of zabofloxacin. Our results revealed that the target compounds were generally less active than the reference against the tested Gram-positive and Gram-negative strains with few exceptions, but compounds 1-5 and 7 showed good activity against MSSA and P. aeruginosa (MICs: 0.25-1 μg/mL). Especially, compounds 3 and 7 (MICs: 0.25 μg/mL) were found to be 4 times more potent than or comparable to levofloxacin against P. aeruginosa, the important conditioned pathogen on hospital infection. Simple structure-activity relationship was also discussed in this paper.
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- K. Drlica, M. Malik, R.J. Kerns and X.L. Zhao, Antimicrob. Agents Chemother., 52, 385 (2008); doi:10.1128/AAC.01617-06.
- D.J. Dwyer, M.A. Kohanski, B. Hayete and J.J. Collins, Mol. Syst. Biol., 3, 1 (2007); doi:10.1038/msb4100135.
- M.L. Liu and H.Y. Guo, World Notes Antibiot., 27, 69 (2006).
- A. Bryskier and J.F. Chantot, Drugs, 49(Suppl. 2), 16 (1995); doi:10.2165/00003495-199500492-00005.
- H. Koga, A. Itoh, S. Murayama, S. Suzue and T. Irikura, J. Med. Chem., 23, 1358 (1980); doi:10.1021/jm00186a014.
- Z. Dang, Y.S. Yang, R.Y. Ji and S.H. Zhang, Bioorg. Med. Chem. Lett., 17, 4523 (2007); doi:10.1016/j.bmcl.2007.05.093.
- X.Y. Wang and Q. Guo, Acta Pharmacol. Sin., 43, 819 (2008).
- Y.B. Zhang, G.Q. Li, M.L. Liu, X.F. You, L.S. Feng, K. Lv, J. Cao and H.Y. Guo, Bioorg. Med. Chem. Lett., 21, 928 (2011); doi:10.1016/j.bmcl.2010.12.073.
- R.N. Jones, D.J. Biedenbach, P.G. Ambrose and M.A. Wikler, Diagn. Microbiol. Infect. Dis., 62, 110 (2008); doi:10.1016/j.diagmicrobio.2008.05.010.
- L.-S. Feng, M.-L. Liu, S. Wang, Y. Chai, K. Lv, G.-Z. Shan, J. Cao, S.-J. Li and H.-Y. Guo, Tetrahedron, 67, 8264 (2011); doi:10.1016/j.tet.2011.08.089.
- MICs were determined as described by the NCCLS (see: National Committee for Clinical Laboratory Standards, Performance Standards for Antimicrobial Susceptibility Testing: 11th Informational Supplement, vol. 21, National Committee for Clinical Laboratory Standards, Wayne, PA, 2001, M100-S11. The MIC was defined as the lowest concentration of each compound resulting in inhibition of visible growth of bacteria after incubation at 35 °C for 18 h.
References
K. Drlica, M. Malik, R.J. Kerns and X.L. Zhao, Antimicrob. Agents Chemother., 52, 385 (2008); doi:10.1128/AAC.01617-06.
D.J. Dwyer, M.A. Kohanski, B. Hayete and J.J. Collins, Mol. Syst. Biol., 3, 1 (2007); doi:10.1038/msb4100135.
M.L. Liu and H.Y. Guo, World Notes Antibiot., 27, 69 (2006).
A. Bryskier and J.F. Chantot, Drugs, 49(Suppl. 2), 16 (1995); doi:10.2165/00003495-199500492-00005.
H. Koga, A. Itoh, S. Murayama, S. Suzue and T. Irikura, J. Med. Chem., 23, 1358 (1980); doi:10.1021/jm00186a014.
Z. Dang, Y.S. Yang, R.Y. Ji and S.H. Zhang, Bioorg. Med. Chem. Lett., 17, 4523 (2007); doi:10.1016/j.bmcl.2007.05.093.
X.Y. Wang and Q. Guo, Acta Pharmacol. Sin., 43, 819 (2008).
Y.B. Zhang, G.Q. Li, M.L. Liu, X.F. You, L.S. Feng, K. Lv, J. Cao and H.Y. Guo, Bioorg. Med. Chem. Lett., 21, 928 (2011); doi:10.1016/j.bmcl.2010.12.073.
R.N. Jones, D.J. Biedenbach, P.G. Ambrose and M.A. Wikler, Diagn. Microbiol. Infect. Dis., 62, 110 (2008); doi:10.1016/j.diagmicrobio.2008.05.010.
L.-S. Feng, M.-L. Liu, S. Wang, Y. Chai, K. Lv, G.-Z. Shan, J. Cao, S.-J. Li and H.-Y. Guo, Tetrahedron, 67, 8264 (2011); doi:10.1016/j.tet.2011.08.089.
MICs were determined as described by the NCCLS (see: National Committee for Clinical Laboratory Standards, Performance Standards for Antimicrobial Susceptibility Testing: 11th Informational Supplement, vol. 21, National Committee for Clinical Laboratory Standards, Wayne, PA, 2001, M100-S11. The MIC was defined as the lowest concentration of each compound resulting in inhibition of visible growth of bacteria after incubation at 35 °C for 18 h.