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Synthesis and biological evaluation of novel d-glucose-derived 1,2,3-triazoles as potential antibacterial and antifungal agents

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Abstract

A series of novel d-glucose-derived 1,2,3-triazoles have been synthesized in excellent yields via Cu(I)-catalyzed 1,3-dipolar cycloaddition by using methyl α-d-glucopyranoside as starting material. All the new compounds were confirmed by 1H NMR, 13C NMR, IR, MS, and HRMS spectra, and their antimicrobial activities were screened against Gram-Positive, Gram-Negative bacteria, and fungi. Bioactive assay manifested that some of the synthesized glucose-derived 1,2,3-triazoles exhibited good antibacterial and antifungal activities. Notably, compound 5k gave the most potent efficiency with MIC50 value of 6 µM against Candida albicans, which was nine-fold more active than the reference drug Fluconazole. It also exhibited good antibacterial activity against Escherichia coli with the MIC50 value of 10.8 µM compared to Chloramphenicol while the corresponding hydrochloride 4k revealed remarkable inhibitory against Bacillus subtilis with an MIC50 value of 11 µM.

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Acknowledgments

This work was partially supported by National Natural Science Foundation of China [No. 21172181, 21372186, 81450110094, 81350110523 (The Research Fellowship for International Young Scientists from International (Regional) Cooperation and Exchange Program)], the key program from Natural Science Foundation of Chongqing (CSTC2012jjB10026), the Specialized Research Fund for the Doctoral Program of Higher Education of China (SRFDP 20110182110007).

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Authors and Affiliations

  1. Institute of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, People’s Republic of China

    Hui-Zhen Zhang, Jin-Jian Wei, Kannekanti Vijaya Kumar, Syed Rasheed & Cheng-He Zhou

  2. Indian Institute of Chemical Technology (IICT), Hyderabad, 500 607, India

    Kannekanti Vijaya Kumar

  3. Department of Chemistry, Hyderabad University, Hyderabad, India

    Syed Rasheed

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  1. Hui-Zhen Zhang
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  2. Jin-Jian Wei
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  3. Kannekanti Vijaya Kumar
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  4. Syed Rasheed
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  5. Cheng-He Zhou
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Correspondence to Cheng-He Zhou.

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Hui-Zhen Zhang and Jin-Jian Wei have contributed equally to this work.

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Zhang, HZ., Wei, JJ., Vijaya Kumar, K. et al. Synthesis and biological evaluation of novel d-glucose-derived 1,2,3-triazoles as potential antibacterial and antifungal agents. Med Chem Res 24, 182–196 (2015). https://doi.org/10.1007/s00044-014-1123-9

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