867068-29-9Relevant articles and documents
Insecticidal heterolignans-Tubuline polymerization inhibitors with activity against chewing pests
Frackenpohl, Jens,Adelt, Isabelle,Antonicek, Horst,Arnold, Christian,Behrmann, Patricia,Blaha, Nicole,Boehmer, Jutta,Gutbrod, Oliver,Hanke, Roman,Hohmann, Sabine,Houtdreve, Marc van,Loesel, Peter,Malsam, Olga,Melchers, Martin,Neufert, Valentina,Peschel, Elisabeth,Reckmann, Udo,Schenke, Thomas,Thiesen, Hans-Peter,Velten, Robert,Vogelsang, Kathrin,Weiss, Hans-Christoph
experimental part, p. 4160 - 4184 (2009/10/17)
Starting from natural product podophyllotoxin 1 substituted heterolignans were identified with promising insecticidal in vivo activity. The impact of substitution in each segment of the core structure was investigated in a detailed SAR study, and variation of substituents in both aromatic moieties afforded derivatives 5 and 43 with broad insecticidal activity against lepidopteran and coleopteran species. In vitro measurements supported by modeling studies indicate that heterolignans 3-134 act as tubuline polymerization inhibitors interacting with the colchicine-binding site. Insect specific structure-activity effects were observed showing that the insecticidal SAR described herein differs from reported cytotoxicity studies.
