Synthesis of andrographolide-related esters as insecticidal and acaricidal agents |
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Authors: | Xiaobo Huang Bingchuan Zhang Hui Xu |
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Institution: | 1. Research Institute of Pesticidal Design & Synthesis, College of Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, China;2. State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjing 300071, China;3. Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry and Pharmacy, Northwest A&F University, Yangling 712100, Shaanxi Province, China |
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Abstract: | 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. |
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Keywords: | Ester Andrographolide Natural-product-based Insecticidal activity Acaricidal activity |
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