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Facile Synthesis and Herbicidal Evaluation of 4H-3,1-Benzoxazin-4-ones and 3H-Quinazolin-4-ones with 2-Phenoxymethyl Substituents
Series of 4H-3,1-benzoxazin-4-ones and 3H-quinazolin-4-ones with phenoxy-methyl substituents were rationally designed and easily synthesized via one-pot N-acylation/ring closure reactions of anthranilic acids with 2-phenoxyacetyl chlorides to yield the 4H-3,1-benzoxazin-4-ones, and subsequently subs...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2012
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268642/ https://www.ncbi.nlm.nih.gov/pubmed/22418925 http://dx.doi.org/10.3390/molecules17033181 |
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author | Aibibuli, Zumuretiguli Wang, Yufeng Tu, Haiyang Huang, Xiaoting Zhang, Aidong |
author_facet | Aibibuli, Zumuretiguli Wang, Yufeng Tu, Haiyang Huang, Xiaoting Zhang, Aidong |
author_sort | Aibibuli, Zumuretiguli |
collection | PubMed |
description | Series of 4H-3,1-benzoxazin-4-ones and 3H-quinazolin-4-ones with phenoxy-methyl substituents were rationally designed and easily synthesized via one-pot N-acylation/ring closure reactions of anthranilic acids with 2-phenoxyacetyl chlorides to yield the 4H-3,1-benzoxazin-4-ones, and subsequently substituted with amino derivatives to obtain the 3H-quinazolin-4-ones. The herbicidal evaluation was performed on the model plants barnyard grass (a monocotyledon) and rape (a dicotyledon), and most of the title compounds displayed high levels of phytotoxicity. The active substructure and inhibitory phenotype analysis indicated that these compounds could be attributed to the class of plant hormone inhibitors. A docking study of several representative compounds with the hormone receptor TIR1 revealed an appreciable conformational match in the active site, implicating these compounds are potential lead hits targeting this receptor. |
format | Online Article Text |
id | pubmed-6268642 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62686422018-12-20 Facile Synthesis and Herbicidal Evaluation of 4H-3,1-Benzoxazin-4-ones and 3H-Quinazolin-4-ones with 2-Phenoxymethyl Substituents Aibibuli, Zumuretiguli Wang, Yufeng Tu, Haiyang Huang, Xiaoting Zhang, Aidong Molecules Article Series of 4H-3,1-benzoxazin-4-ones and 3H-quinazolin-4-ones with phenoxy-methyl substituents were rationally designed and easily synthesized via one-pot N-acylation/ring closure reactions of anthranilic acids with 2-phenoxyacetyl chlorides to yield the 4H-3,1-benzoxazin-4-ones, and subsequently substituted with amino derivatives to obtain the 3H-quinazolin-4-ones. The herbicidal evaluation was performed on the model plants barnyard grass (a monocotyledon) and rape (a dicotyledon), and most of the title compounds displayed high levels of phytotoxicity. The active substructure and inhibitory phenotype analysis indicated that these compounds could be attributed to the class of plant hormone inhibitors. A docking study of several representative compounds with the hormone receptor TIR1 revealed an appreciable conformational match in the active site, implicating these compounds are potential lead hits targeting this receptor. MDPI 2012-03-14 /pmc/articles/PMC6268642/ /pubmed/22418925 http://dx.doi.org/10.3390/molecules17033181 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). |
spellingShingle | Article Aibibuli, Zumuretiguli Wang, Yufeng Tu, Haiyang Huang, Xiaoting Zhang, Aidong Facile Synthesis and Herbicidal Evaluation of 4H-3,1-Benzoxazin-4-ones and 3H-Quinazolin-4-ones with 2-Phenoxymethyl Substituents |
title | Facile Synthesis and Herbicidal Evaluation of 4H-3,1-Benzoxazin-4-ones and 3H-Quinazolin-4-ones with 2-Phenoxymethyl Substituents |
title_full | Facile Synthesis and Herbicidal Evaluation of 4H-3,1-Benzoxazin-4-ones and 3H-Quinazolin-4-ones with 2-Phenoxymethyl Substituents |
title_fullStr | Facile Synthesis and Herbicidal Evaluation of 4H-3,1-Benzoxazin-4-ones and 3H-Quinazolin-4-ones with 2-Phenoxymethyl Substituents |
title_full_unstemmed | Facile Synthesis and Herbicidal Evaluation of 4H-3,1-Benzoxazin-4-ones and 3H-Quinazolin-4-ones with 2-Phenoxymethyl Substituents |
title_short | Facile Synthesis and Herbicidal Evaluation of 4H-3,1-Benzoxazin-4-ones and 3H-Quinazolin-4-ones with 2-Phenoxymethyl Substituents |
title_sort | facile synthesis and herbicidal evaluation of 4h-3,1-benzoxazin-4-ones and 3h-quinazolin-4-ones with 2-phenoxymethyl substituents |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268642/ https://www.ncbi.nlm.nih.gov/pubmed/22418925 http://dx.doi.org/10.3390/molecules17033181 |
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