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New Ciprofloxacin–Dithiocarbamate–Benzyl Hybrids: Design, Synthesis, Antibacterial Evaluation, and Molecular Modeling Studies Publisher



Esfahani EN1 ; Mohammadikhanaposhtani M2 ; Rezaei Z3 ; Valizadeh Y3 ; Rajabnia R4 ; Hassankalhori M5 ; Bandarian F1 ; Faramarzi MA6, 7 ; Samadi N8, 9 ; Amini MR1 ; Mahdavi M1 ; Larijani B1
Authors
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Authors Affiliations
  1. 1. Diabetes Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
  2. 2. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran
  3. 3. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  4. 4. Infectious Diseases and Tropical Medicine Research Center, Babol University of Medical Sciences, Babol, Iran
  5. 5. Drug Design and Development Research Center, Tehran University of Medical Sciences, Tehran, Iran
  6. 6. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  7. 7. Biotechnology Research Center, Tehran University of Medical Sciences, Tehran, Iran
  8. 8. Department of Drug and Food Control, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  9. 9. Pharmaceutical Quality Assurance Research Center, Tehran University of Medical Sciences, Tehran, Iran

Source: Research on Chemical Intermediates Published:2019


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. © 2018, Springer Nature B.V.