Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis, Characterization and Biological Evaluations of Ciprofloxacin Carboxamide Analogues

  • Sultana, Najma (Department of Pharmaceutical Chemistry, Research Institute of Pharmaceutical Sciences, Faculty of Pharmacy, University of Karachi) ;
  • Arayne, Muhammad Saeed (Department of Chemistry, University of Karachi) ;
  • Rizvi, Syeda Bushra Shakeb (Department of Pharmaceutical Chemistry, Faculty of Pharmacy Federal Urdu University of Arts, Science and Technology) ;
  • Haroon, Urooj (Department of Chemistry, Federal Urdu University of Arts, Science and Technology)
  • Received : 2010.06.23
  • Accepted : 2010.11.30
  • Published : 2011.02.20
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Abstract

Present work comprises of synthesis various analogues of ciprofloxacin by introducing new functionality at carboxylic group position via ester aminolysis reaction. For this purpose the carboxylic group at C-3 was esterified and later subjected to nucleophilic attack at the carbonyl carbon by various aromatic amines. Structure of the analogues was confirmed by different techniques i.e. IR, $^1H$ NMR and mass spectrometry. The antibacterial activity of the derivatives was also assessed with the parent against a series of Gram-positive and Gram-negative bacteria. The synthesized compounds showed diverse antimicrobial profile among which most compounds possessed a comparable or better activity in comparison to the ciprofloxacin. Additionally unlike ciprofloxacin, some of the derivatives were also found to show antifungal activity.

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References

  1. Hooper, D. C. Biochim. Biophys. Acta 1998, 1400, 45-61. https://doi.org/10.1016/S0167-4781(98)00127-4
  2. Mascellino, M. T.; Farinelli, S.; Iegri, F.; Iona, E.; De Simone, C. Drugs Expert. Clin. Res. 1998, 24, 139-151.
  3. Kampranis, S. C.; Maxwell, A. J. Biol. Chem. 1998, 273(35), 22615-22626. https://doi.org/10.1074/jbc.273.35.22615
  4. Hooper, D. C. Drug Resist Updates 1999, 2, 38-55. https://doi.org/10.1054/drup.1998.0068
  5. Drlica, K.; Zhao X. Microbiol Mol. Biol. Rev. 1997, 61, 377-392.
  6. Jazayeri, S.; Moshafi, M. H.; Firoozpour, L.; Emami, S.; Rajabalian, S.; Haddad, M.; Pahlavanzadeh, F.; Esnaashari, M.; Shafiee,A.; Foroumadi, A. European Journal of Medicinal Chemistry 2009, 44, 1205-1209. https://doi.org/10.1016/j.ejmech.2008.09.012
  7. Foroumadi, A.; Emami, S.; Mehni, M.; Moshafi, M. H.; Shafiee, A. Bioorganic & Medicinal Chemistry Letters 2005, 15, 4536-4539. https://doi.org/10.1016/j.bmcl.2005.07.005
  8. Chen, Y. L.; Fang, K. C.; Sheu, J. Y.; Hsu, S. L.; Tzeng, C. C. J. Med. Chem. 2001, 44, 2374-2377. https://doi.org/10.1021/jm0100335
  9. Fang, K. C.; Chen, Y. L.; Sheu, J. Y.; Wang, T. C.; Tzeng, C. C. J. Med. Chem. 2000, 43, 3809-3812. https://doi.org/10.1021/jm000153x
  10. Foroumadi, A.; Mansouri, S.; Kiani, Z.; Rahmani, A. Eur. J. Med. Chem. 2003, 38, 851-854. https://doi.org/10.1016/S0223-5234(03)00148-X
  11. Ma, X.; Zhou, W.; Brun, R. Bioorganic & Medicinal Chemistry Letters 2009, 19(3), 986-989. https://doi.org/10.1016/j.bmcl.2008.11.078
  12. Sultana, N.; Arayne, M. S.; Rizvi, S. B. S.; Mesaik, M. A. Bull. Korean Chem. Soc. 2009, 30(10), 2294-2298. https://doi.org/10.5012/bkcs.2009.30.10.2294
  13. Arayne, M. S.; Sultana, N.; Haroon, U.; Mesaik, M. A.; Asif, M. Arch. Pharm. Res. 2009, 32(7), 967-974. https://doi.org/10.1007/s12272-009-1700-5
  14. Bauer, A. W.; Kirby, W. M. M.; Sherris, J. C.; Turck, M. Am. J. Clin. Pathol. 1966, 45, 493-496.
  15. Ozdek, S. C.; Miller, D.; Flynn, P. M.; Flynn, H. W., Jr. Ocular Infections 2006, 14(6), 347-351.

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