Cargando…

Synthesis and Larvicidal Activity of Novel Thenoylhydrazide Derivatives

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 react...

Descripción completa

Detalles Bibliográficos
Autores principales: Song, Gao-Peng, Hu, De-Kun, Tian, Hao, Li, Ya-Sheng, Cao, Yun-Shen, Jin, Hong-Wei, Cui, Zi-Ning
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4785375/
https://www.ncbi.nlm.nih.gov/pubmed/26960713
http://dx.doi.org/10.1038/srep22977
_version_ 1782420399684845568
author Song, Gao-Peng
Hu, De-Kun
Tian, Hao
Li, Ya-Sheng
Cao, Yun-Shen
Jin, Hong-Wei
Cui, Zi-Ning
author_facet Song, Gao-Peng
Hu, De-Kun
Tian, Hao
Li, Ya-Sheng
Cao, Yun-Shen
Jin, Hong-Wei
Cui, Zi-Ning
author_sort Song, Gao-Peng
collection PubMed
description 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.
format Online
Article
Text
id pubmed-4785375
institution National Center for Biotechnology Information
language English
publishDate 2016
publisher Nature Publishing Group
record_format MEDLINE/PubMed
spelling pubmed-47853752016-03-11 Synthesis and Larvicidal Activity of Novel Thenoylhydrazide Derivatives Song, Gao-Peng Hu, De-Kun Tian, Hao Li, Ya-Sheng Cao, Yun-Shen Jin, Hong-Wei Cui, Zi-Ning Sci Rep Article 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. Nature Publishing Group 2016-03-10 /pmc/articles/PMC4785375/ /pubmed/26960713 http://dx.doi.org/10.1038/srep22977 Text en Copyright © 2016, Macmillan Publishers Limited http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/
spellingShingle Article
Song, Gao-Peng
Hu, De-Kun
Tian, Hao
Li, Ya-Sheng
Cao, Yun-Shen
Jin, Hong-Wei
Cui, Zi-Ning
Synthesis and Larvicidal Activity of Novel Thenoylhydrazide Derivatives
title Synthesis and Larvicidal Activity of Novel Thenoylhydrazide Derivatives
title_full Synthesis and Larvicidal Activity of Novel Thenoylhydrazide Derivatives
title_fullStr Synthesis and Larvicidal Activity of Novel Thenoylhydrazide Derivatives
title_full_unstemmed Synthesis and Larvicidal Activity of Novel Thenoylhydrazide Derivatives
title_short Synthesis and Larvicidal Activity of Novel Thenoylhydrazide Derivatives
title_sort synthesis and larvicidal activity of novel thenoylhydrazide derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4785375/
https://www.ncbi.nlm.nih.gov/pubmed/26960713
http://dx.doi.org/10.1038/srep22977
work_keys_str_mv AT songgaopeng synthesisandlarvicidalactivityofnovelthenoylhydrazidederivatives
AT hudekun synthesisandlarvicidalactivityofnovelthenoylhydrazidederivatives
AT tianhao synthesisandlarvicidalactivityofnovelthenoylhydrazidederivatives
AT liyasheng synthesisandlarvicidalactivityofnovelthenoylhydrazidederivatives
AT caoyunshen synthesisandlarvicidalactivityofnovelthenoylhydrazidederivatives
AT jinhongwei synthesisandlarvicidalactivityofnovelthenoylhydrazidederivatives
AT cuizining synthesisandlarvicidalactivityofnovelthenoylhydrazidederivatives