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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| Format: | Article |
| Language: | English |
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MDPI AG
2017-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/22/10/1666 |
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| author | Adilson Vidal Costa Marcos Vinicius Lacerda de Oliveira Roberta Tristão Pinto Luiza Carvalheira Moreira Ediellen Mayara Corrêa Gomes Thammyres de Assis Alves Patrícia Fontes Pinheiro Vagner Tebaldi de Queiroz Larissa Fonseca Andrade Vieira Robson Ricardo Teixeira Waldir Cintra de Jesus Júnior |
| author_facet | Adilson Vidal Costa Marcos Vinicius Lacerda de Oliveira Roberta Tristão Pinto Luiza Carvalheira Moreira Ediellen Mayara Corrêa Gomes Thammyres de Assis Alves Patrícia Fontes Pinheiro Vagner Tebaldi de Queiroz Larissa Fonseca Andrade Vieira Robson Ricardo Teixeira Waldir Cintra de Jesus Júnior |
| author_sort | Adilson Vidal Costa |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-12-19T03:39:47Z |
| format | Article |
| id | doaj.art-a96f88e7294b431fb6411068d1824844 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-19T03:39:47Z |
| publishDate | 2017-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-a96f88e7294b431fb6411068d18248442022-12-21T20:37:17ZengMDPI AGMolecules1420-30492017-10-012210166610.3390/molecules22101666molecules22101666Synthesis of Novel Glycerol-Derived 1,2,3-Triazoles and Evaluation of Their Fungicide, Phytotoxic and Cytotoxic ActivitiesAdilson Vidal Costa0Marcos Vinicius Lacerda de Oliveira1Roberta Tristão Pinto2Luiza Carvalheira Moreira3Ediellen Mayara Corrêa Gomes4Thammyres de Assis Alves5Patrícia Fontes Pinheiro6Vagner Tebaldi de Queiroz7Larissa Fonseca Andrade Vieira8Robson Ricardo Teixeira9Waldir Cintra de Jesus Júnior10Graduate Program in Agrochemistry, Universidade Federal do Espírito Santo, Alto Universitário, S/N, Guararema, Alegre ES 29500-000, BrazilGraduate Program in Agrochemistry, Universidade Federal do Espírito Santo, Alto Universitário, S/N, Guararema, Alegre ES 29500-000, BrazilGraduate Program in Agrochemistry, Universidade Federal do Espírito Santo, Alto Universitário, S/N, Guararema, Alegre ES 29500-000, BrazilGraduate Program in Agrochemistry, Universidade Federal do Espírito Santo, Alto Universitário, S/N, Guararema, Alegre ES 29500-000, BrazilGraduate Program in Plant Production, Universidade Federal do Espírito Santo, Alto Universitário, S/N, Guararema, Alegre ES 29500-000, BrazilGraduate Program in Biotechnology, Universidade Federal do Espírito Santo, Alto Universitário, S/N, Guararema, Alegre ES 29500-000, BrazilGraduate Program in Agrochemistry, Universidade Federal do Espírito Santo, Alto Universitário, S/N, Guararema, Alegre ES 29500-000, BrazilGraduate Program in Agrochemistry, Universidade Federal do Espírito Santo, Alto Universitário, S/N, Guararema, Alegre ES 29500-000, BrazilDepartment of Biology, Universidade Federal de Lavras, Lavras MG 37200-000, BrazilDepartament of Chemistry, Universidade Federal de Viçosa, Av. P.H. Rolfs, S/N, Viçosa MG 36570-900, Brazilersidade Federal de São Carlos, Campus Lagoa do Sino, Buri SP 18290-000, BrazilThe 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.https://www.mdpi.com/1420-3049/22/10/1666glycerol1,2,3-triazolesfungicidecytotoxic activityclick chemistry |
| spellingShingle | Adilson Vidal Costa Marcos Vinicius Lacerda de Oliveira Roberta Tristão Pinto Luiza Carvalheira Moreira Ediellen Mayara Corrêa Gomes Thammyres de Assis Alves Patrícia Fontes Pinheiro Vagner Tebaldi de Queiroz Larissa Fonseca Andrade Vieira Robson Ricardo Teixeira Waldir Cintra de Jesus Júnior Synthesis of Novel Glycerol-Derived 1,2,3-Triazoles and Evaluation of Their Fungicide, Phytotoxic and Cytotoxic Activities Molecules glycerol 1,2,3-triazoles fungicide cytotoxic activity click chemistry |
| 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 | glycerol 1,2,3-triazoles fungicide cytotoxic activity click chemistry |
| url | https://www.mdpi.com/1420-3049/22/10/1666 |
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