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Synthesis and Biological Activities of Diosgenin-Triazole Conjugates with a 1,3-Dipolar Cycloaddition Reaction

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Chemistry of Natural Compounds Aims and scope

A novel series of diosgenin-triazole conjugates (10a–d, 11a–c, 12a–c, 13a–c) was designed and synthesized as antifungal agents by using a 1,3-dipolar cycloaddition reaction in the presence of a Cu(I) catalyst. All the title compounds were characterized by 1H NMR, 13C NMR, and Q-TOF-MS. Results of preliminary antifungal tests against seven human pathogenic fungi in vitro revealed that half of the target compounds exhibited moderate or even better antifungal activities against Y0109 and C. albicans SC5314 species. Compound 10d showed excellent antifungal activities toward C. albicans Y0109 and C. albicans SC5314 than itraconazole, with MIC80 value of 1 μg/mL, respectively.

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Acknowledgment

This work was supported by the National Natural Science Foundation of China (21502223, 81773580), the Science & Technology Commission of Shanghai Municipality (09dZ1976700), and the Department of Science and Technology of Guangdong Province of China (2017A050501032).

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Authors and Affiliations

  1. Department of Biochemistry and Molecular Biology, College of Basic Medical Sciences, Second Military Medical University, 200433, Shanghai, P. R. China

    Jun Liao & Yun Gao

  2. Department of Organic Chemistry, College of Pharmacy, Second Military Medical University, 200433, Shanghai, P. R. China

    Jun Liao, Xiaoyun Chai, Qiuye Wu & Qingjie Zhao

  3. International Institute for Translational Chinese Medicine, Guangzhou University of Chinese Medicine, 510006, Guangzhou, P. R. China

    Guochao Liao

  4. College of Pharmacy, Zhejiang Chinese Medical University, 311400, Hangzhou, P. R. China

    Qiuye Wu

Authors
  1. Jun Liao
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  2. Guochao Liao
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  3. Yun Gao
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  4. Xiaoyun Chai
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  5. Qiuye Wu
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  6. Qingjie Zhao
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Corresponding authors

Correspondence to Qiuye Wu or Qingjie Zhao.

Additional information

Published in Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2021, pp. 920–925.

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Liao, J., Liao, G., Gao, Y. et al. Synthesis and Biological Activities of Diosgenin-Triazole Conjugates with a 1,3-Dipolar Cycloaddition Reaction. Chem Nat Compd 57, 1074–1080 (2021). https://doi.org/10.1007/s10600-021-03552-2

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  • DOI: https://doi.org/10.1007/s10600-021-03552-2

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