New Insecticidal Agents from Halogenation/Acylation of the Furyl-Ring of Fraxinellone

Introduction of the halogen atom or the acyl group at the C-ring of fraxinellone was investigated. Some unexpected halogenation products were obtained with the different chlorination/bromination reagents, and their possible reaction mechanisms were also proposed. Seven key steric structures of 2a’,...

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Autores principales: Guo, Yong, Yang, Ruige, Xu, Hui
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group 2016
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5075773/
https://www.ncbi.nlm.nih.gov/pubmed/27775033
http://dx.doi.org/10.1038/srep35321
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author Guo, Yong
Yang, Ruige
Xu, Hui
author_facet Guo, Yong
Yang, Ruige
Xu, Hui
author_sort Guo, Yong
collection PubMed
description Introduction of the halogen atom or the acyl group at the C-ring of fraxinellone was investigated. Some unexpected halogenation products were obtained with the different chlorination/bromination reagents, and their possible reaction mechanisms were also proposed. Seven key steric structures of 2a’, 2b, 2b’, 2c’, 3a, 3b, and one isomer (5’α-Cl) of 2a were further confirmed by single-crystal X-ray diffraction. Especially compounds 2a, 2a’, 3a and 3c exhibited more potent insecticidal activity than toosendanin. Some structure-activity relationships of tested compounds were also described.
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spelling pubmed-50757732016-10-28 New Insecticidal Agents from Halogenation/Acylation of the Furyl-Ring of Fraxinellone Guo, Yong Yang, Ruige Xu, Hui Sci Rep Article Introduction of the halogen atom or the acyl group at the C-ring of fraxinellone was investigated. Some unexpected halogenation products were obtained with the different chlorination/bromination reagents, and their possible reaction mechanisms were also proposed. Seven key steric structures of 2a’, 2b, 2b’, 2c’, 3a, 3b, and one isomer (5’α-Cl) of 2a were further confirmed by single-crystal X-ray diffraction. Especially compounds 2a, 2a’, 3a and 3c exhibited more potent insecticidal activity than toosendanin. Some structure-activity relationships of tested compounds were also described. Nature Publishing Group 2016-10-24 /pmc/articles/PMC5075773/ /pubmed/27775033 http://dx.doi.org/10.1038/srep35321 Text en Copyright © 2016, The Author(s) 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
Guo, Yong
Yang, Ruige
Xu, Hui
New Insecticidal Agents from Halogenation/Acylation of the Furyl-Ring of Fraxinellone
title New Insecticidal Agents from Halogenation/Acylation of the Furyl-Ring of Fraxinellone
title_full New Insecticidal Agents from Halogenation/Acylation of the Furyl-Ring of Fraxinellone
title_fullStr New Insecticidal Agents from Halogenation/Acylation of the Furyl-Ring of Fraxinellone
title_full_unstemmed New Insecticidal Agents from Halogenation/Acylation of the Furyl-Ring of Fraxinellone
title_short New Insecticidal Agents from Halogenation/Acylation of the Furyl-Ring of Fraxinellone
title_sort new insecticidal agents from halogenation/acylation of the furyl-ring of fraxinellone
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5075773/
https://www.ncbi.nlm.nih.gov/pubmed/27775033
http://dx.doi.org/10.1038/srep35321
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