College of Chemistry and Pharmaceutical Sciences, Research Center of Bio-Pesticides Engineering & Tech. of Shandong Province, Qingdao Agricultural University, Qingdao 266109, China.
Molecules. 2023 Jan 5;28(2):530. doi: 10.3390/molecules28020530.
(1) Background: Scopoletin and scoparone, two naturally occurring coumarins, have garnered considerable attention and have been introduced to the market in China due to their high insecticidal efficacy and low toxicity. To investigate the structure-activity relationship of these coumarins, a series of scopoletin derivatives with aryl sulfate at C7 and different substitutes at C3 were designed and synthesized, and their insecticidal activity was studied. (2) Methods: A total of 28 new scopoletin derivatives were designed and synthesized. Most target compounds exhibited moderate insecticidal activity against the phytophagous mite and the brine shrimp . (3) Results: Among these compounds, compounds and possessed the best insecticidal activities against with LC values of 57.0 and 20.0 μg/mL, respectively, whereas that of the control drug was 15.0 μg/mL. Compound exhibited selective insecticidal activities against , with an LC value of 9.36 μg/mL, whereas its LC value against was 93.0 μg/mL. The enzymatic inhibitory activity on acetylcholinesterase (AChE) showed a consistent tendency with the insecticidal activity. Further molecular docking analyses predicted the binding conformations of these compounds, which showed a good correlation between the insecticidal activity and the binding scores. (4) Conclusions: In general, a decreased electron cloud density of the Δ olefinic bond is beneficial for improving the insecticidal activity against both and . In addition, naphthyl or benzene groups with a sulfate ester at the C7 position could further improve the insecticidal activity against . AChE was implied to be a site of action for potential insecticidal activity. The results provide insight into the rational design of a new generation of effective coumarin insecticides.
（1）背景：香豆素类化合物茴芹素和花椒毒素因杀虫活性高、毒性低而受到广泛关注，已在中国推向市场。为了研究这些香豆素类化合物的构效关系，设计并合成了一系列在 C7 位带有芳基硫酸酯且在 C3 位具有不同取代基的茴芹素衍生物，并研究了它们的杀虫活性。（2）方法：共设计并合成了 28 个新的茴芹素衍生物。大多数目标化合物对植食性螨 和卤虫 均表现出中等的杀虫活性。（3）结果：在这些化合物中，化合物 和 对 具有最佳的杀虫活性，LC 值分别为 57.0 和 20.0 μg/mL，而对照药物的 LC 值为 15.0 μg/mL。化合物 对 表现出选择性的杀虫活性，LC 值为 9.36 μg/mL，而其对 的 LC 值为 93.0 μg/mL。对乙酰胆碱酯酶（AChE）的酶抑制活性与杀虫活性表现出一致的趋势。进一步的分子对接分析预测了这些化合物的结合构象，表明杀虫活性与结合评分之间存在良好的相关性。（4）结论：总的来说，降低Δ烯烃键的电子云密度有利于提高对 和 的杀虫活性。此外，在 C7 位带有萘基或苯磺酸酯的基团可以进一步提高对 的杀虫活性。AChE 可能是潜在杀虫活性的作用靶标。研究结果为合理设计新一代高效香豆素类杀虫剂提供了思路。
