Synthesis of 4β-acyloxypodophyllotoxin analogs modified in the C and E rings as insecticidal agents against Mythimna separata Walker

被引：10
|
作者：
Zhi, Xiaoyan [1 ]
Yu, Xiang [1 ]
Yang, Chun [1 ]
Ding, Guodong [1 ]
Chen, Hui [2 ]
Xu, Hui [1 ]
机构：
[1] Northwest A&F Univ, Coll Sci, Lab Pharmaceut Design & Synth, Yangling 712100, Shaanxi Provinc, Peoples R China
[2] Northwest A&F Univ, Coll Forestry, Yangling 712100, Shaanxi Provinc, Peoples R China
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2014年 / 24卷 / 03期
基金：
中国国家自然科学基金;
关键词：
Podophyllotoxin; 4; beta-Acyloxypodophyllotoxin; Regioselective; Insecticidal activity; Botanical insecticide; Structural modification; Mythimna separata Walker; STEREOSELECTIVE-SYNTHESIS; LEPIDOPTERA-NOCTUIDAE; BIOLOGICAL-ACTIVITIES; ANTIFUNGAL ACTIVITY; ORIENTAL ARMYWORM; NATURAL-PRODUCTS; DERIVATIVES; PODOPHYLLOTOXIN; DEOXYPODOPHYLLOTOXIN; SEMISYNTHESIS;
D O I：
10.1016/j.bmcl.2013.12.105
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
To discover the new natural-product-based insecticidal agents, four series of sixty novel 4 beta-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'-demethylepipodophyllotoxin was regioselectively controlled by the chlorine atom at its C-2' position when 2'-chloro-4'-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. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：765 / 772
页数：8
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