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

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Abstract

We designed and synthesized a series of new ciprofloxacin–dithiocarbamate–benzyl hybrids 5a–n 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.

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Acknowledgements

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

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Authors and Affiliations

  1. Diabetes Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

    Ensieh Nasli Esfahani, Fatemeh Bandarian, Mohammad Reza Amini, Mohammad Mahdavi & Bagher Larijani

  2. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran

    Maryam Mohammadi-Khanaposhtani

  3. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran

    Zahra Rezaei & Yosef Valizadeh

  4. Infectious Diseases and Tropical Medicine Research Center, Babol University of Medical Sciences, Babol, Iran

    Ramazan Rajabnia

  5. Drug Design and Development Research Center, Tehran University of Medical Sciences, Tehran, Iran

    Mahdi Hassankalhori

  6. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran

    Mohammad Ali Faramarzi

  7. Biotechnology Research Center, Tehran University of Medical Sciences, Tehran, Iran

    Mohammad Ali Faramarzi

  8. Department of Drug and Food Control, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran

    Nasrin Samadi

  9. Pharmaceutical Quality Assurance Research Center, Tehran University of Medical Sciences, Tehran, Iran

    Nasrin Samadi

Authors
  1. Ensieh Nasli Esfahani
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  2. Maryam Mohammadi-Khanaposhtani
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  3. Zahra Rezaei
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  5. Ramazan Rajabnia
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  6. Mahdi Hassankalhori
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  7. Fatemeh Bandarian
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  8. Mohammad Ali Faramarzi
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  9. Nasrin Samadi
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  10. Mohammad Reza Amini
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  11. Mohammad Mahdavi
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  12. Bagher Larijani
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Correspondence to Mohammad Mahdavi or Bagher Larijani.

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Esfahani, E.N., Mohammadi-Khanaposhtani, M., Rezaei, Z. et al. New ciprofloxacin–dithiocarbamate–benzyl hybrids: design, synthesis, antibacterial evaluation, and molecular modeling studies. Res Chem Intermed 45, 223–236 (2019). https://doi.org/10.1007/s11164-018-3598-3

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  • DOI: https://doi.org/10.1007/s11164-018-3598-3

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