Synthesis of novel glycerol-derived 1,2,3-triazoles and evaluation of their fungicide, phytotoxic and cytotoxic activities

• Autor(a) principal: Costa, Adilson Vidal
• Data de Publicação: 2017
• Outros Autores: 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
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: LOCUS Repositório Institucional da UFV
• Texto Completo: http://dx.doi.org/10.3390/molecules22101666; http://www.locus.ufv.br/handle/123456789/16553
• topic: Glycerol; 1,2,3-triazoles; Fungicide; Cytotoxic activity; Click chemistry

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.