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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...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group
2016
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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 |
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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 |
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