Diacylhydrazine (DAH)-type compounds were first reported as non-steroidal ecdysone agonists in 1988, a number of which are registered as insecticides for agriculture fields. However, DAHs are specifically toxic to Lepidoptera and exhibit very weak or no activity against other insect orders. It is known that the selective toxicity is caused by the difference of the ligand-binding domain of the ecdysone receptor among species. To date various compounds having different basic structures have been reported as ecdysone agonists, including tetrahydroquinoline, oxazoline, imidazole, acylaminoketone, and ?-methylene- ?-lactam, some of which are not Lepidoptera selective (although these compounds are not on the market). Among them, thiadiazoloimidazole-type compounds were reported to be potent ecdysone agonists, and the ligand-receptor binding interactions are thought to be different from the ligand-receptor binding mode of DAH. Herein we synthesized various thiadiazoloimidazole-type compounds and measured the binding activity to sf-9 lepidopteran insect cells. In addition, the ligand-receptor interactions are discussed based upon in silico docking.

Structure-activity relationships of thiadiazoloimidazole-type ecdysone agonists for binding to sf-9 cells

248th National Meeting (2014)

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