Combinatorial Synthesis of A Series of Alkyl/Alkenylacyloxy Derivatives at the C-28 Position of Toosendanin as Insecticidal Agents

Author(s): Junliang Zhang, Huan Qu, Xiang Yu, Xiaoyan Zhi, Hui Chen, Hui Xu.

Journal Name: Combinatorial Chemistry & High Throughput Screening
Accelerated Technologies for Biotechnology, Bioassays, Medicinal Chemistry and Natural Products Research

Volume 16 , Issue 5 , 2013

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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.

Keywords: C28-alkyl/alkenylacyloxy, botanical insecticide, combinatorial synthesis, insecticidal activity, toosendanin.

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Article Details

VOLUME: 16
ISSUE: 5
Year: 2013
Page: [394 - 399]
Pages: 6
DOI: 10.2174/1386207311316050004
Price: $58

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