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New 7-piperazinylquinolones containing (benzo[d]imidazol-2-yl)methyl moiety as potent antibacterial agents

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Abstract

A series of 7-piperazinylquinolones containing a (benzo[d]imidazol-2-yl)methyl moiety were designed and synthesized as new antibacterial agents. The antibacterial activity of title compounds was evaluated against Gram-positive (Staphylococcus aureus, Staphylococcus epidermidis and Bacillus subtilis) and Gram-negative (Escherichia coli, Pseudomonas aeruginosa and Klebsiella pneumonia) microorganisms. Among the tested compounds, the N1-cyclopropyl derivative 4a showed the highest activity against S. aureus, S. epidermidis, B. subtilis and E. coli (\(\text {MIC} = 0.097\) \(\upmu \)g/mL), being 2–4 times more potent than reference drug norfloxacin. A structure-activity relationship study demonstrated that the effect of the nitro group on the benzimidazole ring depends on the pattern of substitutions on the piperazinylquinolone.

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Acknowledgements

This work was supported by a Grant (No. 833) from the Research Council of Mazandaran University of Medical Sciences, Sari, Iran.

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Authors and Affiliations

  1. Student Research Committee, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran

    Hojat-Allah Arab

  2. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy and Biotechnology Research Center, Tehran University of Medical Sciences, Tehran, Iran

    Mohammad Ali Faramarzi

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

    Nasrin Samadi

  4. Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran

    Hamid Irannejad & Saeed Emami

  5. Department of Medicinal Chemistry, Faculty of Pharmacy and The Institute of Pharmaceutical Sciences (TIPS), Tehran University of Medical Sciences, Tehran, Iran

    Alireza Foroumadi

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  1. Hojat-Allah Arab
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  2. Mohammad Ali Faramarzi
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  3. Nasrin Samadi
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  4. Hamid Irannejad
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Correspondence to Saeed Emami.

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Arab, HA., Faramarzi, M.A., Samadi, N. et al. New 7-piperazinylquinolones containing (benzo[d]imidazol-2-yl)methyl moiety as potent antibacterial agents. Mol Divers 22, 815–825 (2018). https://doi.org/10.1007/s11030-018-9834-3

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  • DOI: https://doi.org/10.1007/s11030-018-9834-3

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