Insects grow by repeating molting that is regulated by a molting hormone, 20-hydroxyecdysone (20E). At the molecular level, 20E binds to the ecdysone receptor (EcR), and the 20E-EcR/USP complex binds to the ecdysone response element to transactivate the various genes. To date, a range of chemical structures for ecdysone agonists that mimic 20E have been reported. Among them, some diacylhydrazine (DAH)-type compounds are used as insecticides in the agriculture fields. The basic structures of other non-steroidal ecdysone agonists are tetrahydroquinoline, oxazoline, acylaminoketone, ?-methylene-?-lactam, imidazole, etc. The binding of imidazole-type compounds to the EcR has been solved by crystal structure analysis and was found to be similar to that of DAH to the EcR of the Lepidoptera insect, Heliothis virescens. In this study, we synthesized N-(2-phenyl-1H-imidazol-1-yl)benzamide analogs with different alkyl groups at the 3- and 4-position and measured the binding affinity to the in vitro translated EcR/USP heterodimer. The molting hormonal activity was also quantitatively evaluated using a reporter gene assay.                                                   

Synthesis of <i>N</i>-(2-phenyl-1<i>H</i>-imidazol-1-yl)benzamide analogs and measurement of binding to the ecdysone receptor and molting hormonal activity using a reporter gene assay

248th National Meeting (2014)

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Synthesis of N-(2-phenyl-1H-imidazol-1-yl)benzamide analogs and measurement of binding to the ecdysone receptor and molting hormonal activity using a reporter gene assay