Bioorganic & Medicinal Chemistry Letters ( IF 2.5 ) Pub Date : 2017-12-19 , DOI: 10.1016/j.bmcl.2017.12.038 Xiaobo Huang , Bingchuan Zhang , Hui Xu
In continuation of our program aimed at the development of natural product-based pesticidal agents, a series of andrographolide-related esters, such as 3,19-dialkyl(aryl)carbonyloxy andrographolide (3a–g), 3-alkyl(aryl)carbonyloxyandrographolide (4a–g), and 19-alkyl(aryl)carbonyloxyandrographolide (5a–g), were prepared. Their structures were well characterized by 1H NMR, IR, optical rotation, HRMS and mp. Especially three-dimensional structures of compounds 3a, 4g, and 5g were unambiguously confirmed by single-crystal X-ray diffraction. Compounds 3a and 5a exhibited good insecticidal and acaricidal activities against Mythimna separata and Tetranychus cinnabarinus. Their structure-activity relationships were also discussed.
中文翻译:
穿心莲内酯相关酯类的杀虫剂和杀螨剂的合成
在继续致力于开发基于天然产物的农药的计划的过程中,一系列与穿心莲内酯有关的酯,例如3,19-二烷基(芳基)羰基氧基穿心莲内酯(3a – g),3-烷基(芳基)羰基氧基穿心莲内酯(4a – g)和19-烷基(芳基)羰基氧基穿心莲内酯(5a – g)均已制备。它们的结构通过1 H NMR,IR,旋光性,HRMS和mp很好地表征。特别是通过单晶X射线衍射明确地确认了化合物3a,4g和5g的三维结构。化合物3a和5a对Mythimna separata和Tetranychus cinnabarinus表现出良好的杀虫和杀螨活性。还讨论了它们的构效关系。