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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...

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Autores principales: 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
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
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.
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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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