Synthesis of new 1,4-disubstituted 1,2,3-triazoles using the CuAAC reaction and determination of their antioxidant activities
| Autor: | 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 |
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| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: | |
| Zdroj: | Anais da Academia Brasileira de Ciências, Vol 93, Iss 3 (2021) |
| Druh dokumentu: | article |
| ISSN: | 1678-2690 0001-3765 |
| DOI: | 10.1590/0001-3765202120201672 |
| Popis: | 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. |
| Databáze: | Directory of Open Access Journals |
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