农药学学报2024，Vol.26Issue(3)：451-461,11.DOI:10.16801/j.issn.1008-7303.2024.0042
1-苯基-5-氨基吡唑类蜕皮激素类似物的合成与杀虫活性
Synthesis and insecticidal activity of 1-phenyl-5-aminopyrazole ecdysteroid analogs
摘要
Abstract
To develop highly efficient and structurally novel insect growth regulators,20 1-phenyl-5-amino pyrazoles were designed and synthesized using ecdysteroid receptor(EcR)as the target and I7(N-(4-cyano-1-phenyl-1H-pyrazol-5-yl)-2-phenylacetamide),a highly active compound discovered by our group,as a lead.All synthesized structures were confirmed by 1H NMR,13C NMR and HRMS.The insecticidal activity of the compounds showed that the lethality of compounds M10,M17 and M18 was more than 20%higher than that of lead compound I7(60%)at a concentration of 250 mg/L.Compound M10 was the most active,exhibiting a lethality rate of 60%at 125 mg/L,which is slightly lower than that of the commercial tebufenozide(70%),and Plutella xylostella treated with this compound showed typical symptoms of ecdysteroid analogue poisoning.The results of the target binding activity of P.xylostella EcR(PxEcR)showed that the compounds M2,M6,M9,M12,M13,M15 and M20 were better than that of compound I7,and that the target binding activity of compound M15(IC50(PxEcR)=2.02 μmol/L)was 11.5 times higher than that of compound I7(IC50(PxEcR)=23.21 μmol/L).The binding mechanism between compounds I7,M10,M15 and EcR receptor was further analyzed by molecular docking and molecular dynamics simulation,which will provide guidance for the further research on insect growth regulators targeting EcR.关键词
蜕皮激素类似物/农药分子设计/小菜蛾/杀虫活性/分子对接/分子动力学模拟Key words
ecdysteroid analogs/pesticide molecular design/Plutella xylostella/insecticidal activity/molecular docking/molecular dynamics simulations分类
医药卫生引用本文复制引用
李秀珍,靳彬艳,崔佳琳,冯彦姣,张晓鸣,张莉..1-苯基-5-氨基吡唑类蜕皮激素类似物的合成与杀虫活性[J].农药学学报,2024,26(3):451-461,11.基金项目
国家自然科学基金项目(21977114). Supported by The National Natural Science Foundation of China(No.21977114). （21977114）
