Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

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
Download PDF
⟨ Previous Next ⟩

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.

Keywords

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 Chemistry2009, 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.

Cited by

  1. ChemInform Abstract: Synthesis, Characterization and Biological Evaluations of Ciprofloxacin Carboxamide Analogues. vol.42, pp.25, 2011, https://doi.org/10.1002/chin.201125154
  2. Novel derivatives of 5-amino-1-cyclopropyl-7-[(3R,5S)3,5-dimethylpiperazine-1-yl]-6,8-difluoro-4-oxo-quinoline-3-carboxylic acid: their synthesis, antimicrobial, antifungal, and urease inhibitory studies vol.23, pp.3, 2014, https://doi.org/10.1007/s00044-013-0699-9
  3. 4-Quinolone Derivatives and Their Activities Against Gram-negative Pathogens vol.55, pp.9, 2018, https://doi.org/10.1002/jhet.3244
  4. Novel Ciprofloxacin Derivatives for Polymer-Based Drug Delivery Systems vol.762, pp.1662-9795, 2018, https://doi.org/10.4028/www.scientific.net/KEM.762.36
  5. Total Syntheses of Lobaric Acid and Its Derivatives from the Antarctic Lichen Stereocaulon alpinum vol.81, pp.6, 2018, https://doi.org/10.1021/acs.jnatprod.8b00227
  6. Fluoroquinolone-3-carboxamide Amino Acid Conjugates: Synthesis, Antibacterial Properties And Molecular Modeling Studies vol.15, pp.None, 2019, https://doi.org/10.2174/1573406415666190904143852
  7. Theoretical molecular predictions and antimicrobial activities of newly synthesized molecular hybrids of norfloxacin and ciprofloxacin vol.57, pp.1, 2011, https://doi.org/10.1002/jhet.3768