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Synthesis of Novel Glycerol-Derived 1,2,3-Triazoles and Evaluation of Their Fungicide, Phytotoxic and Cytotoxic Activities
The synthesis of a series of 1,2,3-triazoles using glycerol as starting material is described. The key step in the preparation of these triazolic derivatives is the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), also known as click reaction, between 4-(azidomethyl)-2,2-dimethyl-1,3-dioxolan...
Autores principales: | , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6151794/ https://www.ncbi.nlm.nih.gov/pubmed/28991165 http://dx.doi.org/10.3390/molecules22101666 |
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author | Costa, Adilson Vidal de Oliveira, Marcos Vinicius Lacerda Pinto, Roberta Tristão Moreira, Luiza Carvalheira Gomes, Ediellen Mayara Corrêa Alves, Thammyres de Assis Pinheiro, Patrícia Fontes de Queiroz, Vagner Tebaldi Vieira, Larissa Fonseca Andrade Teixeira, Robson Ricardo Júnior, Waldir Cintra de Jesus |
author_facet | Costa, Adilson Vidal de Oliveira, Marcos Vinicius Lacerda Pinto, Roberta Tristão Moreira, Luiza Carvalheira Gomes, Ediellen Mayara Corrêa Alves, Thammyres de Assis Pinheiro, Patrícia Fontes de Queiroz, Vagner Tebaldi Vieira, Larissa Fonseca Andrade Teixeira, Robson Ricardo Júnior, Waldir Cintra de Jesus |
author_sort | Costa, Adilson Vidal |
collection | PubMed |
description | The synthesis of a series of 1,2,3-triazoles using glycerol as starting material is described. The key step in the preparation of these triazolic derivatives is the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), also known as click reaction, between 4-(azidomethyl)-2,2-dimethyl-1,3-dioxolane (3) and different terminal alkynes. The eight prepared derivatives were evaluated with regard to their fungicide, phytotoxic and cytotoxic activities. The fungicidal activity was assessed in vitro against Colletotrichum gloeosporioides, the causative agent of papaya anthracnose. It was found that the compounds 1-(1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-1,2,3-triazol-4-yl)-cyclo-hexanol (4g) and 2-(1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-1,2,3-triazol-4-yl)propan-2-ol (4h) demonstrated high efficiency in controlling C. gloeosporioides when compared to the commercial fungicide tebuconazole. The triazoles did not present any phytotoxic effect when evaluated against Lactuca sativa. However, five derivatives were mitodepressive, inducing cell death detected by the presence of condensed nuclei and acted as aneugenic agents in the cell cycle of L. sativa. It is believed that glycerol derivatives bearing 1,2,3-triazole functionalities may represent a promising scaffold to be explored for the development of new agents to control C. gloeosporioides. |
format | Online Article Text |
id | pubmed-6151794 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-61517942018-11-13 Synthesis of Novel Glycerol-Derived 1,2,3-Triazoles and Evaluation of Their Fungicide, Phytotoxic and Cytotoxic Activities Costa, Adilson Vidal de Oliveira, Marcos Vinicius Lacerda Pinto, Roberta Tristão Moreira, Luiza Carvalheira Gomes, Ediellen Mayara Corrêa Alves, Thammyres de Assis Pinheiro, Patrícia Fontes de Queiroz, Vagner Tebaldi Vieira, Larissa Fonseca Andrade Teixeira, Robson Ricardo Júnior, Waldir Cintra de Jesus Molecules Article The synthesis of a series of 1,2,3-triazoles using glycerol as starting material is described. The key step in the preparation of these triazolic derivatives is the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), also known as click reaction, between 4-(azidomethyl)-2,2-dimethyl-1,3-dioxolane (3) and different terminal alkynes. The eight prepared derivatives were evaluated with regard to their fungicide, phytotoxic and cytotoxic activities. The fungicidal activity was assessed in vitro against Colletotrichum gloeosporioides, the causative agent of papaya anthracnose. It was found that the compounds 1-(1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-1,2,3-triazol-4-yl)-cyclo-hexanol (4g) and 2-(1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-1,2,3-triazol-4-yl)propan-2-ol (4h) demonstrated high efficiency in controlling C. gloeosporioides when compared to the commercial fungicide tebuconazole. The triazoles did not present any phytotoxic effect when evaluated against Lactuca sativa. However, five derivatives were mitodepressive, inducing cell death detected by the presence of condensed nuclei and acted as aneugenic agents in the cell cycle of L. sativa. It is believed that glycerol derivatives bearing 1,2,3-triazole functionalities may represent a promising scaffold to be explored for the development of new agents to control C. gloeosporioides. MDPI 2017-10-07 /pmc/articles/PMC6151794/ /pubmed/28991165 http://dx.doi.org/10.3390/molecules22101666 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Costa, Adilson Vidal de Oliveira, Marcos Vinicius Lacerda Pinto, Roberta Tristão Moreira, Luiza Carvalheira Gomes, Ediellen Mayara Corrêa Alves, Thammyres de Assis Pinheiro, Patrícia Fontes de Queiroz, Vagner Tebaldi Vieira, Larissa Fonseca Andrade Teixeira, Robson Ricardo Júnior, Waldir Cintra de Jesus Synthesis of Novel Glycerol-Derived 1,2,3-Triazoles and Evaluation of Their Fungicide, Phytotoxic and Cytotoxic Activities |
title | Synthesis of Novel Glycerol-Derived 1,2,3-Triazoles and Evaluation of Their Fungicide, Phytotoxic and Cytotoxic Activities |
title_full | Synthesis of Novel Glycerol-Derived 1,2,3-Triazoles and Evaluation of Their Fungicide, Phytotoxic and Cytotoxic Activities |
title_fullStr | Synthesis of Novel Glycerol-Derived 1,2,3-Triazoles and Evaluation of Their Fungicide, Phytotoxic and Cytotoxic Activities |
title_full_unstemmed | Synthesis of Novel Glycerol-Derived 1,2,3-Triazoles and Evaluation of Their Fungicide, Phytotoxic and Cytotoxic Activities |
title_short | Synthesis of Novel Glycerol-Derived 1,2,3-Triazoles and Evaluation of Their Fungicide, Phytotoxic and Cytotoxic Activities |
title_sort | synthesis of novel glycerol-derived 1,2,3-triazoles and evaluation of their fungicide, phytotoxic and cytotoxic activities |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6151794/ https://www.ncbi.nlm.nih.gov/pubmed/28991165 http://dx.doi.org/10.3390/molecules22101666 |
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