1599461-41-2Relevant academic research and scientific papers
Stereoselective synthesis of 2α-chloropicropodophyllotoxins and insecticidal activity of their esters against oriental armyworm, Mythimna separata walker
Fan, Lingling,Guo, Yong,Zhi, Xiaoyan,Yu, Xiang,Xu, Hui
, p. 3726 - 3733 (2015/04/22)
As part of ongoing efforts to discover new natural-product-based insecticidal agents, in the present study, an efficient method for the stereoselective α-chlorination at the C-2 position of 2'(2',6')-(di)halogenopodophyllotoxin derivatives was first devel
Stereoselective synthesis of 2α-chloropicropodophyllotoxins and insecticidal activity of their esters against oriental armyworm, mythimna separata walker
Fan, Lingling,Guo, Yong,Zhi, Xiaoyan,Yu, Xiang,Xu, Hui
, p. 3726 - 3733 (2014/05/20)
As part of ongoing efforts to discover new natural-product-based insecticidal agents, in the present study, an efficient method for the stereoselective α-chlorination at the C-2 position of 2′(2′, 6′)-(di)halogenopodophyllotoxin derivatives was first developed. Subsequently, a series of novel esters of 2α-chloro-2′(2′, 6′)-(di)halogenopicropodophyllotoxin with modified C, D, and E rings of podophyllotoxin were smoothly obtained. Finally, all of the title compounds were tested against the pre-third-instar larvae of oriental armyworm (Mythimna separata Walker) at 1 mg/mL. It was found that besides their 2′-halogen-substituted E ring, the stereoselective α-chlorination at the C-2 position of 2′(2′,6′)-(di)halogenopodophyllotoxins was also related to the chlorination reagents. Especially 2α-chloro- 4α-(benzoyl)oxy-2′-chloropicropodophyllotoxin (6e) and 2α-chloro-4α-(2-chlorophenylacyl)oxy-2′- bromopicropodophyllotoxin (8f) showed the most potent insecticidal activities, with final mortality rates of >60%. For 4α-(alkylacyl)oxy derivatives of 2α-chloro-2′(2′,6′)-(di)halogenopicropodophyllotoxin, the effect of the length of their side chain at the C-4 position of podophyllotoxin skeleton on the insecticidal activity was not very obvious. For 4α-(arylacyl)oxy derivatives of 2α-chloro-2′-chloro/ bromopicropodophyllotoxin, an electronic effect of the substituents on their phenyl ring at the C-4 position of podophyllotoxin skeleton on the insecticidal activity was observed.
