title: Combinatorial synthesis of a series of alkyl/alkenylacyloxy derivatives at the C-28 position of toosendanin as insecticidal agents.
abstract: In continuation of our program aimed at the discovery and development of natural-product-based insecticidal agents, we have synthesized eighteen alkyl/alkenylacyloxy derivatives at the C-28 position adopting exo-configuration of toosendanin (3a-r) by the reaction of toosendanin with fatty acids in the presence of N,N'-diisopropylcarbodiimide and 4- dimethylaminopyridine. Their activity was preliminarily evaluated against the pre-third-instar larvae of Mythimna separata Walker in vivo. Especially compounds 3e and 3o displayed the more promising insecticidal activity than their natural precursor, toosendanin. It suggested that for the n-alkyloyloxy series derivatives, the proper length of the side chain R at the C-28 position of toosendanin was very important for their insecticidal activity.
authors.affiliation: Laboratory of Pharmaceutical Design & Synthesis, College of Sciences, Northwest A&F University, Yangling 712100, PR China.
authors.forename: Junliang
authors.initials: J
authors.lastname: Zhang
authors.forename: Huan
authors.initials: H
authors.lastname: Qu
authors.forename: Xiang
authors.initials: X
authors.lastname: Yu
authors.forename: Xiaoyan
authors.initials: X
authors.lastname: Zhi
authors.forename: Hui
authors.initials: H
authors.lastname: Chen
authors.forename: Hui
authors.initials: H
authors.lastname: Xu
mesh_terms: D000818:Animals; D020650:Combinatorial Chemistry Techniques; D004365:Drugs, Chinese Herbal / Q000737:chemistry*; D007313:Insecta / Q000187:drug effects; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007814:Larva / Q000187:drug effects; D015394:Molecular Structure; D014315:Triterpenes
chemical_list: D004365:Drugs, Chinese Herbal; D007306:Insecticides; C036454:toosendanin; D014315:Triterpenes