Abstract
A pair of chemical isomeric structures of novel N-tert-butylphenyl thenoylhydrazide compounds I and II were designed and synthesized. Their structures were characterized by MS, IR, 1H NMR, elemental analysis and X-ray single crystal diffraction. The regioselectivity of the Meerwein arylation reaction and the electrophilic substitution reaction of N-tert-butyl hydrazine were studied by density functional theory (DFT) quantum chemical method. The larvicidal tests revealed that some compounds I had excellent larvicidal activity against Culex pipiens pallens. As the candidates of insect growth regulators (IGRs), the larval growth inhibition and regulation against Culex pipiens pallens were examined for some compounds, especially I1 and I7. Compounds I1 and I7 were further indicated as an ecdysteroid agonist by reporter gene assay on the Spodoptera frugiperda cell line (Sf9 cells). Finally, a molecular docking study of compound I7 was conducted, which was not only beneficial to understand the structure-activity relationship, but also useful for development of new IGRs for the control of mosquitos.
Highlights
Diacylhydrazines were as molting hormone analogs by mimicing the mode of 20-hydroxyecdysone (20E)[1,2] since N’-tert-butyl-N,N’- dibenzoylhydrazine (RH-5849) was reported as the first nonsteroidal ecdysone agonist in the mid of 1980s3,4 (Fig. 1)
Structure-activity relationship studies elucidated that hydrogen bonds between the amide N-H group of diacylhydrazines and amino acid residues of the ligand-binding domains (LBDs) of ecdysone receptor (EcR) played a critical role in bioactivity[35,36]
For the purpose of discovering novel lead compounds with bioactivity, a pair of chemical isomeric structures of N-tert-butylphenyl thenoylhydrazide compounds I and II were designed and synthesized in this letter
Summary
Diacylhydrazines were as molting hormone analogs by mimicing the mode of 20-hydroxyecdysone (20E)[1,2] since N’-tert-butyl-N,N’- dibenzoylhydrazine (RH-5849) was reported as the first nonsteroidal ecdysone agonist in the mid of 1980s3,4 (Fig. 1). The difference between the binding modes revealed new insights to improve the agonist activity of diacylhydrazines by modifying the aromatic ring moiety away from the t-butyl group. For the purpose of discovering novel lead compounds with bioactivity, a pair of chemical isomeric structures of N-tert-butylphenyl thenoylhydrazide compounds I and II were designed and synthesized in this letter.
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