Anais da Academia Brasileira de Ciências (Jun 2021)

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

  • JOSEFA A. DA CUNHA LIMA,
  • JADSON DE FARIAS SILVA,
  • COSME S. SANTOS,
  • RODRIGO R.A. CAIANA,
  • MARCÍLIO M. DE MORAES,
  • CLAUDIO A.G. DA CÂMARA,
  • JULIANO C.R. FREITAS

DOI
https://doi.org/10.1590/0001-3765202120201672
Journal volume & issue
Vol. 93, no. 3

Abstract

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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.

Keywords