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Coumarin-derived azolyl ethanols: synthesis, antimicrobial evaluation and preliminary action mechanism

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Abstract

A series of coumarin-derived azolyl ethanols including imidazolyl, triazolyl, tetrazolyl, benzotriazolyl, thiol-imidazolyl and thiol-triazolyl ones were conveniently synthesized and characterized by IR, 1H NMR, 13C NMR and high-resolution mass spectra (HRMS) spectra. Some of the prepared compounds showed appropriate logPow values and effective antibacterial and antifungal activities. Noticeably, compound 14 with bis-triazolyl ethanol group exhibited low minimal inhibitory concentration (MIC) value of 8 mg/mL against MRSA, which was comparable or even superior to reference drugs Norfloxacin (MIC=8 mg/mL) and Chloramphenicol (MIC=16 mg/mL). It could also effectively inhibit the growth of the tested fungal strains compared to Fluconazole. Further binding studies of coumarin 14 with calf thymus DNA were investigated by UV-Vis absorption and fluorescence spectroscopy. It was found that compound 14 could interact with calf thymus DNA by groove binding to form 14-DNA complex via both hydrogen bonds and van der Waals force, which might be the factor to exert the powerful antimicrobial activity.

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Authors and Affiliations

  1. Institute of Bioorganic & Medicinal Chemistry; Key Laboratory of Applied Chemistry of Chongqing Municipality; School of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, China

    Xin-Mei Peng, Kannekanti Vijaya Kumar, Guri L.V. Damu & Cheng-He Zhou

  2. Postdoctoral fellow from Indian Institute of Chemical Technology, Hyderabad, 500607, India

    Kannekanti Vijaya Kumar & Guri L.V. Damu

Authors
  1. Xin-Mei Peng
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  2. Kannekanti Vijaya Kumar
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  3. Guri L.V. Damu
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  4. Cheng-He Zhou
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Correspondence to Cheng-He Zhou.

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Peng, XM., Kumar, K.V., Damu, G.L. et al. Coumarin-derived azolyl ethanols: synthesis, antimicrobial evaluation and preliminary action mechanism. Sci. China Chem. 59, 878–894 (2016). https://doi.org/10.1007/s11426-015-0351-0

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  • DOI: https://doi.org/10.1007/s11426-015-0351-0

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