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: Costa, Adilson Vidal, Oliveira, Marcos Vinicius Lacerda de, Pinto, Roberta Tristão, Moreira, Luiza Carvalheira, Gomes, Ediellen Mayara Corrêa, Alves, Thammyres de Assis, Pinheiro, Patrícia Fontes, Queiroz, Vagner Tebaldi de, Vieira, Larissa Fonseca Andrade, Teixeira, Robson Ricardo, Jesus Júnior, Waldir Cintra de
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2017
País:Brasil
Recursos:Universidade Federal de Viçosa (UFV)
Repositorio:LOCUS Repositório Institucional da UFV
Idioma:inglés
OAI Identifier:oai:locus.ufv.br:123456789/16553
Acesso em linha:http://dx.doi.org/10.3390/molecules22101666
http://www.locus.ufv.br/handle/123456789/16553
Access Level:acceso abierto
Palavra-chave:Glycerol
1,2,3-triazoles
Fungicide
Cytotoxic activity
Click chemistry
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spelling Synthesis of novel glycerol-derived 1,2,3-triazoles and evaluation of their fungicide, phytotoxic and cytotoxic activitiesGlycerol1,2,3-triazolesFungicideCytotoxic activityClick chemistryThe 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.Molecules2018-01-19T12:50:36Z2018-01-19T12:50:36Z2017-10-07info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlepdfapplication/pdf1420-3049http://dx.doi.org/10.3390/molecules22101666http://www.locus.ufv.br/handle/123456789/16553eng22(10), E1666, Oct. 2017info:eu-repo/semantics/openAccessreponame:LOCUS Repositório Institucional da UFVinstname:Universidade Federal de Viçosa (UFV)instacron:UFVCosta, Adilson VidalOliveira, Marcos Vinicius Lacerda dePinto, Roberta TristãoMoreira, Luiza CarvalheiraGomes, Ediellen Mayara CorrêaAlves, Thammyres de AssisPinheiro, Patrícia FontesQueiroz, Vagner Tebaldi deVieira, Larissa Fonseca AndradeTeixeira, Robson RicardoJesus Júnior, Waldir Cintra de2024-07-12T08:40:03Zoai:locus.ufv.br:123456789/16553Repositório InstitucionalPUBhttps://www.locus.ufv.br/oai/requestfabiojreis@ufv.bropendoar:21452024-07-12T08:40:03LOCUS Repositório Institucional da UFV - Universidade Federal de Viçosa (UFV)false
dc.title.none.fl_str_mv 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
spellingShingle Synthesis of novel glycerol-derived 1,2,3-triazoles and evaluation of their fungicide, phytotoxic and cytotoxic activities
Costa, Adilson Vidal
Glycerol
1,2,3-triazoles
Fungicide
Cytotoxic activity
Click chemistry
title_short 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_sort Synthesis of novel glycerol-derived 1,2,3-triazoles and evaluation of their fungicide, phytotoxic and cytotoxic activities
dc.creator.none.fl_str_mv Costa, Adilson Vidal
Oliveira, Marcos Vinicius Lacerda de
Pinto, Roberta Tristão
Moreira, Luiza Carvalheira
Gomes, Ediellen Mayara Corrêa
Alves, Thammyres de Assis
Pinheiro, Patrícia Fontes
Queiroz, Vagner Tebaldi de
Vieira, Larissa Fonseca Andrade
Teixeira, Robson Ricardo
Jesus Júnior, Waldir Cintra de
author Costa, Adilson Vidal
author_facet Costa, Adilson Vidal
Oliveira, Marcos Vinicius Lacerda de
Pinto, Roberta Tristão
Moreira, Luiza Carvalheira
Gomes, Ediellen Mayara Corrêa
Alves, Thammyres de Assis
Pinheiro, Patrícia Fontes
Queiroz, Vagner Tebaldi de
Vieira, Larissa Fonseca Andrade
Teixeira, Robson Ricardo
Jesus Júnior, Waldir Cintra de
author_role author
author2 Oliveira, Marcos Vinicius Lacerda de
Pinto, Roberta Tristão
Moreira, Luiza Carvalheira
Gomes, Ediellen Mayara Corrêa
Alves, Thammyres de Assis
Pinheiro, Patrícia Fontes
Queiroz, Vagner Tebaldi de
Vieira, Larissa Fonseca Andrade
Teixeira, Robson Ricardo
Jesus Júnior, Waldir Cintra de
author2_role author
author
author
author
author
author
author
author
author
author
dc.subject.por.fl_str_mv Glycerol
1,2,3-triazoles
Fungicide
Cytotoxic activity
Click chemistry
topic Glycerol
1,2,3-triazoles
Fungicide
Cytotoxic activity
Click chemistry
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.
publishDate 2017
dc.date.none.fl_str_mv 2017-10-07
2018-01-19T12:50:36Z
2018-01-19T12:50:36Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv 1420-3049
http://dx.doi.org/10.3390/molecules22101666
http://www.locus.ufv.br/handle/123456789/16553
identifier_str_mv 1420-3049
url http://dx.doi.org/10.3390/molecules22101666
http://www.locus.ufv.br/handle/123456789/16553
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 22(10), E1666, Oct. 2017
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv pdf
application/pdf
dc.publisher.none.fl_str_mv Molecules
publisher.none.fl_str_mv Molecules
dc.source.none.fl_str_mv reponame:LOCUS Repositório Institucional da UFV
instname:Universidade Federal de Viçosa (UFV)
instacron:UFV
instname_str Universidade Federal de Viçosa (UFV)
instacron_str UFV
institution UFV
reponame_str LOCUS Repositório Institucional da UFV
collection LOCUS Repositório Institucional da UFV
repository.name.fl_str_mv LOCUS Repositório Institucional da UFV - Universidade Federal de Viçosa (UFV)
repository.mail.fl_str_mv fabiojreis@ufv.br
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score 15,198674

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