Synthesis of new 1,4-disubstituted 1,2,3-triazoles using the CuAAC reaction and determination of their antioxidant activities

• Main Author: CUNHA LIMA,JOSEFA A. DA
• Publication Date: 2021
• Other Authors: DE FARIAS SILVA,JADSON, SANTOS,COSME S., CAIANA,RODRIGO R.A., DE MORAES,MARCÍLIO M., DA CÂMARA,CLAUDIO A.G., FREITAS,JULIANO C.R.
• Format: Article
• Language: eng
• Source: Anais da Academia Brasileira de Ciências (Online)
• Download full: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0001-37652021000500603
• topic: Antioxidant activity; Free radicals; 1,2,3-Triazole; CuAAC Reaction

Abstract This study describes the synthesis and antioxidant activity of new 1,4-disubstituted 1,2,3-triazoles. These compounds were generated semi-synthetically using the Cu(I)-catalysed azide-alkyne cycloaddition (CuAAC) reaction between ethyl 2-azidoacetate and terminal acetylenes derived from the natural products carvacrol, eugenol, isovanillin, thymol and vanillin. The products were obtained at 50 to 80% yield and characterised through several spectrographic techniques. Antioxidant activity was assayed using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2’-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS). The products exhibited moderate antioxidant activity, with ethyl 2-(4-((4-formyl-2-methoxyphenoxy)methyl)-1H-1,2,3-triazol-1-yl) acetate showing the highest antioxidant capacity (EC50 = 75.5 µg/mL) among the generated 1,4-disubstituted 1,2,3-triazoles. In conclusion, the generation of these compounds opens new possibilities for the development of new antioxidant agents.