Synthesis of Novel Glycerol-Derived 1,2,3-Triazoles and Evaluation of Their Fungicide, Phytotoxic and Cytotoxic Activities
AbstractThe 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. View Full-Text
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Costa, A.V.; Oliveira, M.V.L.; Pinto, R.T.; Moreira, L.C.; Gomes, E.M.C.; Alves, T.A.; Pinheiro, P.F.; Queiroz, V.T.; Vieira, L.F.A.; Teixeira, R.R.; Júnior, W.C.J. Synthesis of Novel Glycerol-Derived 1,2,3-Triazoles and Evaluation of Their Fungicide, Phytotoxic and Cytotoxic Activities. Molecules 2017, 22, 1666.
Costa AV, Oliveira MVL, Pinto RT, Moreira LC, Gomes EMC, Alves TA, Pinheiro PF, Queiroz VT, Vieira LFA, Teixeira RR, Júnior WCJ. Synthesis of Novel Glycerol-Derived 1,2,3-Triazoles and Evaluation of Their Fungicide, Phytotoxic and Cytotoxic Activities. Molecules. 2017; 22(10):1666.Chicago/Turabian Style
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; Júnior, Waldir Cintra de Jesus. 2017. "Synthesis of Novel Glycerol-Derived 1,2,3-Triazoles and Evaluation of Their Fungicide, Phytotoxic and Cytotoxic Activities." Molecules 22, no. 10: 1666.
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