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  • Title: Synthesis of 4β-acyloxypodophyllotoxin analogs modified in the C and E rings as insecticidal agents against Mythimna separata Walker.
    Author: Zhi X, Yu X, Yang C, Ding G, Chen H, Xu H.
    Journal: Bioorg Med Chem Lett; 2014 Feb 01; 24(3):765-72. PubMed ID: 24412075.
    Abstract:
    To discover the new natural-product-based insecticidal agents, four series of sixty novel 4β-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.
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