title: Synthesis and Larvicidal Activity of Novel Thenoylhydrazide Derivatives.
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, (1)H 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.
authors.affiliation: Guangdong Province Key Laboratory of Microbial Signals and Disease Control, South China Agricultural University, Guangzhou, 510642, China.|College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China.
authors.forename: Gao-Peng
authors.initials: GP
authors.lastname: Song
authors.affiliation: Guangdong Province Key Laboratory of Microbial Signals and Disease Control, South China Agricultural University, Guangzhou, 510642, China.
authors.forename: De-Kun
authors.initials: DK
authors.lastname: Hu
authors.affiliation: Guangdong Province Key Laboratory of Microbial Signals and Disease Control, South China Agricultural University, Guangzhou, 510642, China.
authors.forename: Hao
authors.initials: H
authors.lastname: Tian
authors.affiliation: Guangdong Province Key Laboratory of Microbial Signals and Disease Control, South China Agricultural University, Guangzhou, 510642, China.
authors.forename: Ya-Sheng
authors.initials: YS
authors.lastname: Li
authors.affiliation: Guangdong Province Key Laboratory of Microbial Signals and Disease Control, South China Agricultural University, Guangzhou, 510642, China.
authors.forename: Yun-Shen
authors.initials: YS
authors.lastname: Cao
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China.
authors.forename: Hong-Wei
authors.initials: HW
authors.lastname: Jin
authors.affiliation: Guangdong Province Key Laboratory of Microbial Signals and Disease Control, South China Agricultural University, Guangzhou, 510642, China.
authors.forename: Zi-Ning
authors.initials: ZN
authors.lastname: Cui
mesh_terms: D000818:Animals; D003465:Culex / Q000187:drug effects / Q000472:pathogenicity; D006801:Humans; D006834:Hydrazines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D007605:Juvenile Hormones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D007814:Larva / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy; D062105:Molecular Docking Simulation; D018411:Spodoptera / Q000187:drug effects / Q000472:pathogenicity; D013329:Structure-Activity Relationship
chemical_list: D006834:Hydrazines; D007306:Insecticides; D007605:Juvenile Hormones; C029424:hydrazine