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Synthesis and in vitro Antimycobacterial Activity of Ciprofloxacin Acetyl Isatin Derivatives
Corresponding Author(s) : Zaosheng Lv
Asian Journal of Chemistry,
Vol. 29 No. 5 (2017): Vol 29 Issue 5
Abstract
Ten novel acetyl isatin derivatives of ciprofloxacin with marked improvement in lipophilicity, compared to the parent drug ciprofloxacin, were designed, synthesized and evaluated for their in vitro antimycobacterial activity against M. smegmatis and M. tuberculosis H37Rv. All the targets (MIC: 2-128 μg/mL) exhibited inhibitory activity against the above bacterial strains. The most active compound 3h (MIC: 2 μg/mL) was found to be two fold more potent than isoniazid and comparable to rifampin against M. smegmatis. Compound 3g has a potency that of rifampin against M. tuberculosis H37Rv. The result indicated that the lipophilicity of the tested targets is not the sole factor affecting the antimycobacterial activity.
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- World Health Organization, Global Tuberculosis Control: A Short Update to the 2009 Report. WHO Report, Geneva (2009).
- L.-S. Feng, M.-L. Liu, B. Wang, Y. Chai, X.-Q. Hao, S. Meng and H.-Y. Guo, Eur. J. Med. Chem., 45, 3407 (2010); https://doi.org/10.1016/j.ejmech.2010.04.027.
- J. Crofton, P. Choculet and D. Maher, Guidelines for the Management of Drug-Resistant Tuberculosis WHO/TB/96-210 (Rev.1). World Health Organization, Geneva (1997).
- D. Sriram, A. Aubry, P. Yogeeswari and L.M. Fisher, Bioorg. Med. Chem. Lett., 16, 2982 (2006); https://doi.org/10.1016/j.bmcl.2006.02.065.
- A. González, J. Quirante, J. Nieto, M.R. Almeida, M.J. Saraiva, A. Planas, G. Arsequell and G. Valencia, Bioorg. Med. Chem. Lett., 19, 5270 (2009); https://doi.org/10.1016/j.bmcl.2009.03.004.
- T. Aboul-Fadl and F.A.S. Bin-Jubair, Int. J. Res. Pharm. Sci., 1, 133 (2010).
- L.S. Feng, M.L. Liu, S. Zhang, Y. Chai, B. Wang, Y.B. Zhang, K. Lv, Y. Guan, H.Y. Guo and C.L. Xiao, Eur. J. Med. Chem., 46, 341 (2011); https://doi.org/10.1016/j.ejmech.2010.11.023.
- D. Sriram, P. Yogeeswari, J.S. Basha, D.R. Radha and V. Nagaraja, Bioorg. Med. Chem., 13, 5774 (2005); https://doi.org/10.1016/j.bmc.2005.05.063.
- S.N. Pandeya, D. Sriram, P. Yogeeswari and S. Ananthan, Chemotherapy, 47, 266 (2001); https://doi.org/10.1159/000048533.
- M.M. Ismail, M.M. Kamel, L.W. Mohamed and S.I. Faggal, Molecules, 17, 4811 (2012); https://doi.org/10.3390/molecules17054811
References
World Health Organization, Global Tuberculosis Control: A Short Update to the 2009 Report. WHO Report, Geneva (2009).
L.-S. Feng, M.-L. Liu, B. Wang, Y. Chai, X.-Q. Hao, S. Meng and H.-Y. Guo, Eur. J. Med. Chem., 45, 3407 (2010); https://doi.org/10.1016/j.ejmech.2010.04.027.
J. Crofton, P. Choculet and D. Maher, Guidelines for the Management of Drug-Resistant Tuberculosis WHO/TB/96-210 (Rev.1). World Health Organization, Geneva (1997).
D. Sriram, A. Aubry, P. Yogeeswari and L.M. Fisher, Bioorg. Med. Chem. Lett., 16, 2982 (2006); https://doi.org/10.1016/j.bmcl.2006.02.065.
A. González, J. Quirante, J. Nieto, M.R. Almeida, M.J. Saraiva, A. Planas, G. Arsequell and G. Valencia, Bioorg. Med. Chem. Lett., 19, 5270 (2009); https://doi.org/10.1016/j.bmcl.2009.03.004.
T. Aboul-Fadl and F.A.S. Bin-Jubair, Int. J. Res. Pharm. Sci., 1, 133 (2010).
L.S. Feng, M.L. Liu, S. Zhang, Y. Chai, B. Wang, Y.B. Zhang, K. Lv, Y. Guan, H.Y. Guo and C.L. Xiao, Eur. J. Med. Chem., 46, 341 (2011); https://doi.org/10.1016/j.ejmech.2010.11.023.
D. Sriram, P. Yogeeswari, J.S. Basha, D.R. Radha and V. Nagaraja, Bioorg. Med. Chem., 13, 5774 (2005); https://doi.org/10.1016/j.bmc.2005.05.063.
S.N. Pandeya, D. Sriram, P. Yogeeswari and S. Ananthan, Chemotherapy, 47, 266 (2001); https://doi.org/10.1159/000048533.
M.M. Ismail, M.M. Kamel, L.W. Mohamed and S.I. Faggal, Molecules, 17, 4811 (2012); https://doi.org/10.3390/molecules17054811