Synthesis of 4尾-acyloxypodophyllotoxin analogs modified in the C and E rings as insecticidal agents against Mythimna separata Walker
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- 作者：Xiaoyan Zhi ; Xiang Yu ; Chun Yang ; Guodong Ding ; Hui Chen ; Hui Xu
- 关键词：Podophyllotoxin ; 4尾-Acyloxypodophyllotoxin ; Regioselective ; Insecticidal activity ; Botanical insecticide ; Structural modification ; Mythimna separata Walker
- 刊名：Bioorganic and Medicinal Chemistry Letters
- 出版年：1 February, 2014
- 年：2014
- 卷：24
- 期：3
- 页码：765-772
- 全文大小：2857 K
文摘
To discover the new natural-product-based insecticidal agents, four series of sixty novel 4尾-acyloxypodophyllotoxin analogs modified in the C and E rings were prepared, and their insecticidal activity was tested against the pre-third-instar larvae of oriental armyworm, Mythimna separata (Walker) in vivo at the concentration of 1 mg/mL. It demonstrated that the position of the dioxo group on the E-ring of 4鈥?demethylepipodophyllotoxin was regioselectively controlled by the chlorine atom at its C-2鈥?position when 2鈥?chloro-4鈥?demethylepipodophyllotoxin was oxidized by sodium periodate. Among all the derivatives, IIIi exhibited the best potent insecticidal activity with the final mortality rate of 63.3%. To alkylacyloxy series, the proper length of the side chain at the C-4 position of Ia-g, IIa-g and IIIa-g was important for their insecticidal activity.