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Design and synthesis of novel miconazole-based ciprofloxacin hybrids as potential antimicrobial agents

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Abstract

We report herein the design and synthesis of a series of novel miconazole-based ciprofloxacin hybrids with remarkable antimicrobial activities by introducing antifungal fragments to the clinic drug ciprofloxacin. Bioactive assay manifested that 1-cyclopropyl-7-[4-[1-(2,4-difluorophenyl)-2-(1H-imidazol-1-yl)ethyl]piperazin-1-yl]-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid displayed good in vitro biological activities, which were comparable or even better than the reference drugs, miconazole and ciprofloxacin. Especially for Bacillus subtilis, the 1-cyclopropyl-7-[4-[1-(2,4-difluorophenyl)-2-(1H-imidazol-1-yl)ethyl]piperazin-1-yl]-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid(0.25 μg/cm3) was eightfold more potent than the parent drug ciprofloxacin (2 μg/cm3). Our prepared hybrids obviously have promises to be further developed as antimicrobial agents.

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Authors and Affiliations

  1. Department of Animal Science and Technology, Hebei North University, Zhangjiakou, China

    Xiao-Long Gu

  2. Department of Pharmacy, Hebei North University, Zhangjiakou, China

    Hong-Bin Liu

  3. Key Laboratory of Preventive Veterinary Medicine in Hebei Province, Hebei Normal University of Science and Technology, Qinhuangdao, China

    Qing-Hui Jia & Jie-Feng Li

  4. Department of Animal Science, Institute of Animal Science of Hebei, Baoding, China

    Yan-Long Liu

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  1. Xiao-Long Gu
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  2. Hong-Bin Liu
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  3. Qing-Hui Jia
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  4. Jie-Feng Li
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  5. Yan-Long Liu
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Correspondence to Xiao-Long Gu.

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Gu, XL., Liu, HB., Jia, QH. et al. Design and synthesis of novel miconazole-based ciprofloxacin hybrids as potential antimicrobial agents. Monatsh Chem 146, 713–720 (2015). https://doi.org/10.1007/s00706-014-1364-9

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  • DOI: https://doi.org/10.1007/s00706-014-1364-9

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