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

Combinatorial Synthesis of a Series of Alkyl/Alkenylacyloxy Derivatives at the C-28 Position of Toosendanin as Insecticidal Agents.
Comb Chem High Throughput Screen. 2013 Jan 9;
Authors: Zhang J, Qu H, Yu X, Zhi X, Chen H, Xu H
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.
PMID: 23305141 [PubMed - as supplied by publisher]

Source: Combinatorial Chemistry and High Throughput Screening - January 9, 2013 Category: Chemistry Authors: Zhang J, Qu H, Yu X, Zhi X, Chen H, Xu H Tags: Comb Chem High Throughput Screen Source Type: research