张羲, 谢世爽, 胡展, 张北京, 刘启凤, 丁晓帆, 谢佳, 邵雨, 孙然锋. 天然杀线虫先导化合物Waltherione A类似物的合成及杀线虫活性[J]. 农药学学报, 2022, 24(2): 272-279. DOI: 10.16801/j.issn.1008-7303.2021.0150
    引用本文: 张羲, 谢世爽, 胡展, 张北京, 刘启凤, 丁晓帆, 谢佳, 邵雨, 孙然锋. 天然杀线虫先导化合物Waltherione A类似物的合成及杀线虫活性[J]. 农药学学报, 2022, 24(2): 272-279. DOI: 10.16801/j.issn.1008-7303.2021.0150
    ZHANG Xi, XIE Shishuang, HU Zhan, ZHANG Beijing, LIU Qifeng, DING Xiaofan, XIE Jia, SHAO Yu, SUN Ranfeng. Synthesis and nematicidal activity of natural nematicidal lead compound Waltherione A analogues[J]. Chinese Journal of Pesticide Science, 2022, 24(2): 272-279. DOI: 10.16801/j.issn.1008-7303.2021.0150
    Citation: ZHANG Xi, XIE Shishuang, HU Zhan, ZHANG Beijing, LIU Qifeng, DING Xiaofan, XIE Jia, SHAO Yu, SUN Ranfeng. Synthesis and nematicidal activity of natural nematicidal lead compound Waltherione A analogues[J]. Chinese Journal of Pesticide Science, 2022, 24(2): 272-279. DOI: 10.16801/j.issn.1008-7303.2021.0150

    天然杀线虫先导化合物Waltherione A类似物的合成及杀线虫活性

    Synthesis and nematicidal activity of natural nematicidal lead compound Waltherione A analogues

    • 摘要: 为了找出天然杀线虫先导生物碱Waltherione A的关键药效基团并简化其结构,以2,3-二甲氧基苯甲醛和3,4-二甲氧基苯甲醛为原料,经过分子内傅克烷基化反应形成苯并七元氧桥环,并用不同的取代基与桥环相连,合成了12个Waltherione A类似物,其中8个化合物未见文献报道,所有目标化合物的结构均通过核磁共振氢谱(1H NMR)、碳谱(13C NMR)及高分辨质谱(HRMS)确证。采用浸虫法测定了目标化合物对南方根结线虫Meloidogyne incognita的杀虫活性。结果表明:目标化合物杀线虫的活性均低于Waltherione A,其中化合物 A-12 在200 μg/mL下对南方根结线虫2龄幼虫72 h的致死率为69.7%。 A-12 的杀线虫活性高于其他目标化合物,表明芳香取代基与苯并七元氧桥环相连时对化合物活性的提升存在积极作用,这为进一步的结构优化提供了方向。

       

      Abstract: To find out the key pharmacores of Waltherione A which is a natural nematicidal lead alkaloid and simplify its structure, twelve Waltherione A analogues were synthesized from 2,3-dimethoxybenzaldehyde and 3,4-dimethoxybenzaldehyde through intramolecular Friedel-Crafts alkylation reaction, and connected with the bridge ring with different substituents. Among them, eight compounds have not been reported in the literature. The structures of all target compounds were confirmed by 1H NMR,13C NMR and HRMS. The nematicidal activity of the target compounds against Meloidogyne incognita was determined by the immersion method. The results showed that the nematicidal activity of all the target compounds was lower than that of Waltherione A. The 72-h mortality of compound A-12 against the 2nd instar larvae of M. incognita was 69.7% at 200 μg/mL, and the nematicidal activity of compound A-12 was higher in comparation with other compounds. The results showed that the aromatic substituents connected with bridge ring had a positive effect on the activity of the compound, which provides a direction for further structural optimization.

       

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