Semisynthesis and quantitative structure-activity relationship (QSAR) study of novel aromatic esters of 4'-demethyl-4-deoxypodophyllotoxin as insecticidal agents.
By using podophyllotoxin as a phytoinsecticidal lead compound, 15 novel aromatic esters of 4'-demethyl-4-deoxypodophyllotoxin were semisynthesized and preliminarily tested for their insecticidal activity against the pre-third-instar larvae of Mythimna separata Walker in vivo for the first time. Among all of the tested compounds, especially two compounds, 4m and 4o, containing a pyridinyl group, for which final corrected mortality rates against M. separata at 1 mg/mL were 62.9 and 59.2%, respectively, showed the most promising and pronounced insecticidal activity as compared with toosendanin, a commercial insecticide derived from Melia azedarach . The quantitative structure-activity relationships (QSAR) of compounds 4a-4o showed that the relative number of benzene rings and final heat of formation were very important descriptors to their insecticidal activity.
Xu
Hui
H
Laboratory of Pharmaceutical Design and Synthesis, College of Life Sciences, Northwest A&F University, Yangling 712100, Shannxi Province, People's Republic of China. orgxuhui@nwsuaf.edu.cn
Wang
Juanjuan
J
Sun
Huijun
H
Lv
Min
M
Tian
Xuan
X
Yao
Xiaojun
X
Zhang
Xing
X
D000818:Animals; D001554:Benzene / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry; D007814:Larva; D009036:Moths; D011034:Podophyllotoxin / Q000031:analogs & derivatives* / Q000737:chemistry; D021281:Quantitative Structure-Activity Relationship
C508085:4'-demethyldesoxypodophyllotoxin; D004952:Esters; D007306:Insecticides; D001554:Benzene; D011034:Podophyllotoxin