GUO Bingbo, JIANG Biaobiao, DONG Yawen, JIN Xiaoyu, CUI Li, ZHANG Li, YANG Xinling. Design, synthesis and insecticidal activity of novel 4,5,6,7-tetrahydro-2H-indazole hydrazide derivatives targeting ecdysone receptor[J]. Chinese Journal of Pesticide Science, 2022, 24(1): 39-48. DOI: 10.16801/j.issn.1008-7303.2021.0174
    Citation: GUO Bingbo, JIANG Biaobiao, DONG Yawen, JIN Xiaoyu, CUI Li, ZHANG Li, YANG Xinling. Design, synthesis and insecticidal activity of novel 4,5,6,7-tetrahydro-2H-indazole hydrazide derivatives targeting ecdysone receptor[J]. Chinese Journal of Pesticide Science, 2022, 24(1): 39-48. DOI: 10.16801/j.issn.1008-7303.2021.0174

    Design, synthesis and insecticidal activity of novel 4,5,6,7-tetrahydro-2H-indazole hydrazide derivatives targeting ecdysone receptor

    • In order to discover insect growth regulators with new structures, 25 novel 4,5,6,7-tetrahydro-2H-indazole hydrazide derivatives were designed and synthesized by the method of linking active substructures with the lead compound C based on the ecdysone receptor (EcR). The structures of these target compounds were confirmed by 1H NMR, 13C NMR and HRMS. Moreover, molecular docking study revealed that all target compounds had a good binding force with the EcR , wherein the compound I-15 had the similar binding mode with EcR as tebufenozide, which can bind well with the active site of EcR. And the protein binding experiments showed that the binding activity of I-15 to EcR was 75.8%±7.2% at a concentration of 40 mg/L. In addition, preliminary bioassay results showed that some target compounds had certain insecticidal activity against the Plutella xylostella at 500 mg/L, but their activities were not as good as tebufenozide and C . The ClogP values of target compounds were lower than the lead compound, which indicated that their liposolubility was not good enough to penetrate the insect cuticle, resulting in poor insecticidal activity. This work provides important clues for the further structure optimization.
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