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Synthesis and biological activity of amide derivatives derived from natural product Waltherione F

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Abstract

Structural optimization based on natural products has become an effective way to develop new fungicides, which provides important guiding significance for practicing the new development concept and promoting the green development of pesticides. In this project, the target compounds containing 4-quinolone and piperazine substructures based on waltherione F were synthesized through the combination of the fungicidal amide lead compound X-I-4 discovered in our previous work and various of fungicidal piperazine derivatives. Screening of their biological activities suggested that products I-3, I-5, II-3, II-7, II-10, II-11 and II-13 displayed higher inhibition rates against Rhizoctonia solani than other tested compounds. The in vitro cellular cytotoxicity assay revealed that compounds II-6 and II-11 exhibited higher cytotoxicity against HepG2 than other tested compounds. The fluorescence characteristics investigation showed that the absolute fluorescence QY value of the methanol solution of the compound I-6 was higher than those of I-2, I-3, I-7 and I-8, which was further elucidated by TD-DFT.

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Funding

This research was supported by the National Natural Science Foundation of China (No. 32001929), the National Innovation and Entrepreneurship Training Program for College Students (No. 202110447013, 202110447032), and the Innovation and Entrepreneurship Training Program for College Students of Liaocheng University (No. CXCY2020Y116).

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Authors and Affiliations

  1. College of Agriculture, Liaocheng University, Liaocheng, 252000, China

    Hongbin Fang, Zhanfang Chen, Xuewen Hua, Wenrui Liu, Chenmeng Xue, Yi Liu, Xiaohe Zhu, Man Yuan, Shuang Cheng & Dzmitry Bazhanau

  2. College of Pharmacy, Liaocheng University, Liaocheng, 252000, China

    Bingxiang Wang

  3. College of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng, 252000, China

    Jing Ru

  4. College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou, 310014, China

    Yanhong Cui

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  1. Hongbin Fang
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Correspondence to Xuewen Hua, Bingxiang Wang or Yanhong Cui.

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Fang, H., Chen, Z., Hua, X. et al. Synthesis and biological activity of amide derivatives derived from natural product Waltherione F. Med Chem Res 31, 485–496 (2022). https://doi.org/10.1007/s00044-022-02852-8

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  • DOI: https://doi.org/10.1007/s00044-022-02852-8

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