title: Semisynthesis and quantitative structure-activity relationship (QSAR) study of novel aromatic esters of 4'-demethyl-4-deoxypodophyllotoxin as insecticidal agents.
abstract: 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.
authors.affiliation: 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
authors.forename: Hui
authors.initials: H
authors.lastname: Xu
authors.forename: Juanjuan
authors.initials: J
authors.lastname: Wang
authors.forename: Huijun
authors.initials: H
authors.lastname: Sun
authors.forename: Min
authors.initials: M
authors.lastname: Lv
authors.forename: Xuan
authors.initials: X
authors.lastname: Tian
authors.forename: Xiaojun
authors.initials: X
authors.lastname: Yao
authors.forename: Xing
authors.initials: X
authors.lastname: Zhang
mesh_terms: 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
chemical_list: C508085:4'-demethyldesoxypodophyllotoxin; D004952:Esters; D007306:Insecticides; D001554:Benzene; D011034:Podophyllotoxin