title: Natural products-based insecticidal agents 11. Synthesis and insecticidal activity of novel 4α-arylsulfonyloxybenzyloxy-2β-chloropodophyllotoxin derivatives against Mythimna separata Walker in vivo.
abstract: In continuation of our program aimed at the discovery and development of natural products-based insecticidal agents, 14 novel 4α-arylsulfonyloxybenzyloxy-2β-chloropodophyllotoxin derivatives were stereoselectively semisynthesized from podophyllotoxin, and preliminarily evaluated for their insecticidal activity against the pre-third-instar larvae of Mythimna separata Walker in vivo. Especially compounds 9c' and 9g' exhibited the most promising and pronounced insecticidal activity than toosendanin, a commercial insecticide derived from Melia azedarach at 1mg/mL. Generally, it was preliminarily demonstrated that arylsulfonyloxy groups at the C-2 position of benzyloxy moiety and the length of the side chain on the benzenesulfonyloxy group of 4α-arylsulfonyloxybenzyloxy-2β-chloropodophyllotoxins might be important for the insecticidal activity.
authors.affiliation: Laboratory of Pharmaceutical Design and Synthesis, College of Sciences, Northwest A&F University, Yangling 712100, China. orgxuhui@nwsuaf.edu.cn
authors.forename: Hui
authors.initials: H
authors.lastname: Xu
authors.forename: Jun-Liang
authors.initials: JL
authors.lastname: Zhang
mesh_terms: D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D004305:Dose-Response Relationship, Drug; D004353:Drug Evaluation, Preclinical; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D007814:Larva / Q000187:drug effects*; D008958:Models, Molecular; D008968:Molecular Conformation; D009036:Moths / Q000187:drug effects*; D011034:Podophyllotoxin / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D007306:Insecticides; D011034:Podophyllotoxin