Natural products-based insecticidal agents 7. Semisynthesis and insecticidal activity of novel 4alpha-alkyloxy-2-chloropodophyllotoxin derivatives against Mythimna separata Walker in vivo

Bioorg Med Chem Lett. 2010 Sep 1;20(17):5009-12. doi: 10.1016/j.bmcl.2010.07.050. Epub 2010 Jul 16.

Abstract

In continuation of our program aimed at the discovery and development of natural products-based insecticidal agents, 16 novel 4alpha-alkyloxy-2-chloropodophyllotoxin derivatives were semisynthesized from podophyllotoxin, and preliminarily evaluated for their insecticidal activity against the pre-third-instar larvae of Mythimna separata Walker in vivo. Among all the tested derivatives, especially compounds 4b, 4e, 4g, and 4p exhibited more promising and pronounced insecticidal activity than toosendanin, a commercial insecticide derived from Melia azedarach. Generally, it was obviously demonstrated that the length of straight-chain or branched-chain alkyloxy, and heteroatom-containing cycloalkyloxy at the C-4 position of 2-chloropodophyllotoxin were very important for the insecticidal activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Biological Products / pharmacology*
  • Insecticides / chemical synthesis*
  • Insecticides / chemistry
  • Insecticides / pharmacology*
  • Models, Molecular
  • Moths*
  • Podophyllotoxin / analogs & derivatives*
  • Podophyllotoxin / chemical synthesis
  • Podophyllotoxin / pharmacology
  • X-Ray Diffraction

Substances

  • Biological Products
  • Insecticides
  • Podophyllotoxin