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Vol. 26 No. 1 (2014): Vol 26 Issue 1

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Design, Synthesis and Antibacterial Evaluation of Novel Fluoroquinolone and its Derivatives

https://doi.org/10.14233/ajchem.2014.15572
Kang-Min Wang
Key Laboratory of Green Chemistry and Technology of Ministry of Education at Sichuan University, College of Chemistry, Sichuan University, No. 29 Wangjiang Road, Chengdu 610064, Sichuan Province, P.R. China
Yuan-Cheng Qin
Key Laboratory of Green Chemistry and Technology of Ministry of Education at Sichuan University, College of Chemistry, Sichuan University, No. 29 Wangjiang Road, Chengdu 610064, Sichuan Province, P.R. China
Guan-Jun Cheng
Key Laboratory of Green Chemistry and Technology of Ministry of Education at Sichuan University, College of Chemistry, Sichuan University, No. 29 Wangjiang Road, Chengdu 610064, Sichuan Province, P.R. China
Hua-Jun Zhu
Sichuan Kelun Pharmaceutical Co. Ltd, 18, 19/F, 2/Building, Jinjiang Times Garden, 107 Jinli West Road, Chengdu 610067, P.R. China
Long Liang
Sichuan Kelun Pharmaceutical Co. Ltd, 18, 19/F, 2/Building, Jinjiang Times Garden, 107 Jinli West Road, Chengdu 610067, P.R. China
Zhi-Peng Cheng
Sichuan Kelun Pharmaceutical Co. Ltd, 18, 19/F, 2/Building, Jinjiang Times Garden, 107 Jinli West Road, Chengdu 610067, P.R. China
Mei-Ming Luo
Key Laboratory of Green Chemistry and Technology of Ministry of Education at Sichuan University, College of Chemistry, Sichuan University, No. 29 Wangjiang Road, Chengdu 610064, Sichuan Province, P.R. China

Corresponding Author(s) : Mei-Ming Luo

luomm@scu.edu.cn

Asian Journal of Chemistry, Vol. 26 No. 1 (2014): Vol 26 Issue 1

Abstract

Gatifloxacin isomers, [1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(2-methyl-1-piperazinyl)-4-oxo-3-quinoline carboxylic acid] and a series of its derivatives were designed and synthesized and evaluated for their in vitro antibacterial activities. Preliminary results indicated that the tested compounds GI1, GI2, GI3 and GI4 demonstrated excellent activity against Staph. epidermidis. In addition, compounds GI1, GI3 and GI4 show MIC 0.015 μg/mL against Klebsiella peneumoniae. It is worth noting that compound GI2 has been found to exhibit the most prominent activity against all of the tested stains. On the basis of these promising results, some tested compounds could be selected as potential drugs candidate for further evaluation.

Keywords

Gatifloxacin isomers 8-Methoxyfluoroquinolones 2-Methylpiperazine Antibacterial activities
Wang, K.-M., Qin, Y.-C., Cheng, G.-J., Zhu, H.-J., Liang, L., Cheng, Z.-P., & Luo, M.-M. (2013). Design, Synthesis and Antibacterial Evaluation of Novel Fluoroquinolone and its Derivatives. Asian Journal of Chemistry, 26(1), 209–215. https://doi.org/10.14233/ajchem.2014.15572
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References
  1. H. Koga, A. Itoh, S. Murayama, S. Suzue and T. Irikura, J. Med. Chem., 23, 1358 (1980); doi:10.1021/jm00186a014.
  2. (a) S. Emami, A. Shafiee and A. Foroumadi, Mini Rev. Med. Chem., 6, 375 (2006); doi:10.2174/138955706776361493.; (b) S.N. Pandeya, D. Sriram, G. Nath and E. De Clercq, Eur. J. Med. Chem., 35, 249 (2000); doi:10.1016/S0223-5234(00)00125-2.; (c) A. Foroumadi, S. Emami, S. Pournourmohammadi, A. Kharazmi and A. Shafiee, Eur. J. Med. Chem., 40, 1346 (2005); doi:10.1016/j.ejmech.2005.07.002.; (d) D.C. Hooper, Lancet Infect. Dis., 2, 530 (2002); doi:10.1016/S1473-3099(02)00369-9.; (e) D.T. Bearden and L.H. Danziger, Pharmacotherapy, 21, 224S (2001); doi:10.1592/phco.21.16.224S.33997.; (f) L.J.V. Piddock, Drugs, 58(Supplement 2), 11 (1999); doi:10.2165/00003495-199958002-00003.
  3. (a) P.S. Lietman, Drugs, 49(Supplement 2), 159 (1995); doi:10.2165/00003495-199500492-00026.; (b) M.E. Falagas, P.I. Rafailidis and E.S. Rosmarakis, J. Antimicrob. Agents, 29, 374 (2007); doi:10.1016/j.ijantimicag.2006.11.011.
  4. S.J. Projan, Curr. Opin. Pharmacol., 2, 513 (2002); doi:10.1016/S1471-4892(02)00197-2.
  5. (a) K. Coleman, Drug Discov. Today Ther. Strateg., 1, 455 (2004); doi:10.1016/j.ddstr.2004.08.015.; (b) A.V. Shindikar and C.L. Viswanathan, Bioorg. Med. Chem. Lett., 15, 1803 (2005); doi:10.1016/j.bmcl.2005.02.037.
  6. (a) H. Kondo, F. Sakamoto, Y. Kodera and G. Tsukamoto, J. Med. Chem., 29, 2020 (1986); doi:10.1021/jm00160a037.; (b) H. Kondo, F. Sakamoto, T. Uno, Y. Kawahata and G. Tsukamoto, J. Med. Chem., 32, 671 (1989); doi:10.1021/jm00123a029.; (c) M.E. Jung, E.C. Yang, B.T. Vu, M. Kiankarimi, E. Spyrou and J. Kaunitz, J. Med. Chem., 42, 3899 (1999); doi:10.1021/jm990015b.
  7. 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.
  8. R. Sánchez-Martín, J.M. Campos, A. Conejo-García, O. Cruz-López, M. Banez-Coronel, A. Rodríguez-González, M.A. Gallo, J.C. Lacal and A. Espinosa, J. Med. Chem., 48, 3354 (2005); doi:10.1021/jm049061o.
  9. S.H. Zhao, R. Pine, J. Domagala and K. Drlica, Antimicrob. Agents Chemother., 43, 661 (1999).
  10. H. Schelleman, W.B. Bilker, C.M. Brensinger, F. Wan and S. Hennessy, Clin. Pharmacol. Ther., 88, 214 (2010); doi:10.1038/clpt.2010.74. (b) F.J. Villasante, L. Gude, S.P. Fernandez, O. Alonso, E. Garcia and A. Cosme, Org. Process Res. Dev., 12, 900 (2008); doi: 10.1021/op800042a.
  11. T.F. Ge, P.Y.P. Law, H.Y. Wong and Y.Y. Ho, Eur. J. Pharmacol., 573, 70 (2007); doi:10.1016/j.ejphar.2007.07.038.
  12. Y. Mizuki, M. Kamaura, T. Yamaguchi, Y. Sekine and M. Hashimoto, Arzneimittelforschung, 39, 593 (1989).
  13. T. Miyamoto, J. Matsumoto, K. Chiba, H. Egawa, K. Shibamori, A. Minamida, Y. Nishimura, H. Okada, M. Kataoka, M. Fujita, T. Hirose and J. Nakano, J. Med. Chem., 33, 1645 (1990); doi:10.1021/jm00168a018.
  14. A. Leonardi, G. Motta, C. Boi, R. Testa, E. Poggesi, P.G. De Benedetti and M.C. Menziani, J. Med. Chem., 42, 427 (1999); doi:10.1021/jm9805337.
  15. E. Ravina, C. Teran, L. Santana, N. Garcia and I. Estevez, Hetreocycles, 31, 1967 (1990); doi:10.3987/COM-90-5493.
  16. D.A. Allemandi, F.L. Alovero and R.H. Manzo, J. Antimicrob. Chemother., 34, 261 (1994); doi:10.1093/jac/34.2.261.
  17. J.P. Sanchez, R.D. Gogliotti, J.M. Domagala, S.J. Gracheck, M.D. Huband, J.A. Sesnie, M.A. Cohen and M.A. Shapiro, J. Med. Chem., 38, 4478 (1995); doi:10.1021/jm00022a013.
  18. G. Anquetin, J. Greiner, N. Mahmoudi, M. Santillana-Hayat, R. Gozalbes, K. Farhati, F. Derouin, A. Aubry, E. Cambau and P. Vierling, Eur. J. Med. Chem., 41, 1478 (2006); doi:10.1016/j.ejmech.2006.07.003.
  19. MICs were determined as described by the NCCLS ( see National Committee for Clinical Laboratory Standards. Performance Standards for Antimicrobial Susceptibility Testing: 11th Informational Supplement; National Committee for Clinical Laboratory Standards: P.A. Wayne, 2001; Vol. 21, No. 1, M100-S11). The MIC was defined as the lowest concentration of each compound resulting in inhibition of visible growth of bacteria after incubation at 37°C for 18-24 h.
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