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Research on Chemical Intermediates

, Volume 45, Issue 2, pp 223–236 | Cite as

New ciprofloxacin–dithiocarbamate–benzyl hybrids: design, synthesis, antibacterial evaluation, and molecular modeling studies

  • Ensieh Nasli Esfahani
  • Maryam Mohammadi-Khanaposhtani
  • Zahra Rezaei
  • Yosef Valizadeh
  • Ramazan Rajabnia
  • Mahdi Hassankalhori
  • Fatemeh Bandarian
  • Mohammad Ali Faramarzi
  • Nasrin Samadi
  • Mohammad Reza Amini
  • Mohammad MahdaviEmail author
  • Bagher LarijaniEmail author
Article
  • 40 Downloads

Abstract

We designed and synthesized a series of new ciprofloxacin–dithiocarbamate–benzyl hybrids 5an as potential antibacterial agents. All of the synthesized compounds were screened for in vitro antibacterial activity against four bacterial strains (Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli, and Pseudomonas aeruginosa). The antibacterial results indicated that some of the synthesized compounds showed remarkable activity, comparable to their parent drug ciprofloxacin. Among the synthesized compounds, the 4-nitro derivative 5n, exhibited the most antibacterial activity against S. aureus, S. epidermidis, and E. coli. The antibacterial activity of this compound against S. aureus and E. coli was twofold higher than that of its parent ciprofloxacin. Molecular modeling of compound 5n was also investigated in the active site of E. coli DNA gyrase.

Keywords

Ciprofloxacin Dithiocarbamate Docking study Antibacterial activity 

Notes

Acknowledgements

This research was supported by grants from the research council of Tehran University of Medical Sciences and INSF (Iran National Science Foundation).

Compliance with ethical standards

Conflict of interest

The authors have declared no conflict of interest.

Supplementary material

11164_2018_3598_MOESM1_ESM.docx (8.8 mb)
Supplementary material 1 (DOCX 9022 kb)

References

  1. 1.
    I.M. Gould, Int. J. Antimicrob. Agents 32, S2 (2008)CrossRefGoogle Scholar
  2. 2.
    D.M. Livermore, Int. J. Antimicrob. Agents 39, 283 (2012)CrossRefGoogle Scholar
  3. 3.
    U. Theuretzbacher, Curr. Opin. Pharmacol. 11, 433 (2011)CrossRefGoogle Scholar
  4. 4.
    W. Witte, C. Cuny, I. Klare, U. Nübel, B. Strommenger, G. Werner, Int. J. Med. Microbiol. 298, 365 (2008)CrossRefGoogle Scholar
  5. 5.
    K. Lal, P. Yadav, A. Kumar, A. Kumar, A.K. Paul, Bioorg. Chem. 77, 236 (2018)CrossRefGoogle Scholar
  6. 6.
    C. Viegas-Junior, A. Danuello, V. da Silva Bolzani, E.J. Barreiro, C.A.M. Fraga, Curr. Med. Chem. 14, 1829 (2007)CrossRefGoogle Scholar
  7. 7.
    F. Vafadarnejad, M. Mahdavi, E. Karimpour-Razkenari, N. Edraki, B. Sameem, M. Khanavi, M. Saeedi, T. Akbarzadeh, Bioorg. Chem. 77, 311 (2018)CrossRefGoogle Scholar
  8. 8.
    M. Mohammadi-Khanaposhtani, M. Safavi, R. Sabourian, M. Mahdavi, M. Pordeli, M. Saeedi, S.K. Ardestani, A. Foroumadi, A. Shafiee, T. Akbarzadeh, Mol. Divers. 19, 787 (2015)CrossRefGoogle Scholar
  9. 9.
    M. Mohammadi-Khanaposhtani, M. Shabani, M. Faizi, I. Aghaei, R. Jahani, Z. Sharafi, N.S. Zafarghandi, M. Mahdavi, T. Akbarzadeh, S. Emami, A. Shafiee, A. Foroumadi, Eur. J. Med. Chem. 112, 91 (2016)CrossRefGoogle Scholar
  10. 10.
    M.L. Liu, H.Y. Guo, World Notes Antibiot. 27, 69 (2006)Google Scholar
  11. 11.
    H.J. Zeiler, K. Grohe, in Ciprofloxacin, ed. by H.C. Neu, D.S. Reeves (Vieweg + Teubner Verlag, Wiesbaden, 1986), p. 14CrossRefGoogle Scholar
  12. 12.
    Y. Wang, G.L. Damu, J.S. Lv, R.X. Geng, D.C. Yang, C.H. Zhou, Bioorg. Med. Chem. Lett. 22, 5363 (2012)CrossRefGoogle Scholar
  13. 13.
    G.E.D.A. Abuo-Rahma, H.A. Sarhan, G.F. Gad, Bioorg. Med. Chem. Lett. 17, 3879 (2009)CrossRefGoogle Scholar
  14. 14.
    M.Y. Mentese, H. Bayrak, Y. Uygun, A. Mermer, S. Ulker, S.A. Karaoglu, N. Demirbas, Eur. J. Med. Chem. 67, 230 (2013)CrossRefGoogle Scholar
  15. 15.
    T. Plech, B. Kaproń, A. Paneth, U. Kosikowska, A. Malm, A. Strzelczyk, P. Stączek, Ł. Świątek, B. Rajtar, M. Polz-Dacewicz, Eur. J. Med. Chem. 97, 94 (2015)CrossRefGoogle Scholar
  16. 16.
    T. Plech, M. Wujec, U. Kosikowska, A. Malm, B. Rajtar, M. Polz-Dacewicz, Eur. J. Med. Chem. 60, 128–134 (2013)CrossRefGoogle Scholar
  17. 17.
    Q. Li, J. Xing, H. Cheng, H. Wang, J. Wang, S. Wang, J. Zhou, H. Zhang, Chem. Biol. Drug Des. 85, 79 (2015)CrossRefGoogle Scholar
  18. 18.
    P.C. Sharma, A. Jain, S. Jain, R. Pahwa, M.S. Yar, J. Enzyme Inhib. Med. Chem. 25, 577 (2010)CrossRefGoogle Scholar
  19. 19.
    S. Wang, X.D. Jia, M.L. Liu, Y. Lu, H.Y. Guo, Bioorg. Med. Chem. Lett. 22, 5971 (2012)CrossRefGoogle Scholar
  20. 20.
    N. Manav, A.K. Mishra, N.K. Kaushik, Spectrochim. Acta A 65, 32 (2006)CrossRefGoogle Scholar
  21. 21.
    S.M. Mamba, A.K. Mishra, B.B. Mamba, P.B. Njobeh, M.F. Dutton, E. Fosso-Kankeu, Spectrochim. Acta A 77, 579 (2010)CrossRefGoogle Scholar
  22. 22.
    F. Shaheen, A. Badshah, M. Gielen, M. Dusek, K. Fejfarova, D. de Vos, B. Mirza, Organomet. Chem. 692, 3019 (2007)CrossRefGoogle Scholar
  23. 23.
    G. Cascio, L. Lorenzi, D. Caglio, E. Manghisi, F. Arcamone, G. Guanti, G. Satta, G. Morandotti, R. Sperning, Farmaco 51, 189 (1996)Google Scholar
  24. 24.
    E.J. Baron, S.M. Finegold, Diagn. Microbiol. 171 (1990)Google Scholar

Copyright information

© Springer Nature B.V. 2018

Authors and Affiliations

  • Ensieh Nasli Esfahani
    • 1
  • Maryam Mohammadi-Khanaposhtani
    • 2
  • Zahra Rezaei
    • 3
  • Yosef Valizadeh
    • 3
  • Ramazan Rajabnia
    • 4
  • Mahdi Hassankalhori
    • 5
  • Fatemeh Bandarian
    • 1
  • Mohammad Ali Faramarzi
    • 6
    • 7
  • Nasrin Samadi
    • 8
    • 9
  • Mohammad Reza Amini
    • 1
  • Mohammad Mahdavi
    • 1
    Email author
  • Bagher Larijani
    • 1
    Email author
  1. 1.Diabetes Research Center, Endocrinology and Metabolism Clinical Sciences InstituteTehran University of Medical SciencesTehranIran
  2. 2.Cellular and Molecular Biology Research Center, Health Research InstituteBabol University of Medical SciencesBabolIran
  3. 3.Department of Medicinal Chemistry, Faculty of PharmacyTehran University of Medical SciencesTehranIran
  4. 4.Infectious Diseases and Tropical Medicine Research CenterBabol University of Medical SciencesBabolIran
  5. 5.Drug Design and Development Research CenterTehran University of Medical SciencesTehranIran
  6. 6.Department of Pharmaceutical Biotechnology, Faculty of PharmacyTehran University of Medical SciencesTehranIran
  7. 7.Biotechnology Research CenterTehran University of Medical SciencesTehranIran
  8. 8.Department of Drug and Food Control, Faculty of PharmacyTehran University of Medical SciencesTehranIran
  9. 9.Pharmaceutical Quality Assurance Research CenterTehran University of Medical SciencesTehranIran

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