Synthesis of new 1,4-disubstituted 1,2,3-triazoles using the CuAAC reaction and determination of their antioxidant activities
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...
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| Format: | Article |
| Language: | English |
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Academia Brasileira de Ciências
2021-06-01
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| Series: | Anais da Academia Brasileira de Ciências |
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| Online Access: | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0001-37652021000500603&tlng=en |
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| author | 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 |
| author_facet | 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 |
| author_sort | JOSEFA A. DA CUNHA LIMA |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-17T23:22:55Z |
| format | Article |
| id | doaj.art-efc882d3bbb846f8a5f11791e7b4054c |
| institution | Directory Open Access Journal |
| issn | 1678-2690 |
| language | English |
| last_indexed | 2024-12-17T23:22:55Z |
| publishDate | 2021-06-01 |
| publisher | Academia Brasileira de Ciências |
| record_format | Article |
| series | Anais da Academia Brasileira de Ciências |
| spelling | doaj.art-efc882d3bbb846f8a5f11791e7b4054c2022-12-21T21:28:51ZengAcademia Brasileira de CiênciasAnais da Academia Brasileira de Ciências1678-26902021-06-0193310.1590/0001-3765202120201672Synthesis of new 1,4-disubstituted 1,2,3-triazoles using the CuAAC reaction and determination of their antioxidant activitiesJOSEFA A. DA CUNHA LIMAhttps://orcid.org/0000-0002-2004-3804JADSON DE FARIAS SILVAhttps://orcid.org/0000-0002-6039-2857COSME S. SANTOShttps://orcid.org/0000-0001-7812-9494RODRIGO R.A. CAIANAhttps://orcid.org/0000-0002-7935-6143MARCÍLIO M. DE MORAEShttps://orcid.org/0000-0002-7597-6775CLAUDIO A.G. DA CÂMARAhttps://orcid.org/0000-0002-8331-9302JULIANO C.R. FREITAShttps://orcid.org/0000-0003-4617-4084Abstract 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.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0001-37652021000500603&tlng=enAntioxidant activityFree radicals1,2,3-TriazoleCuAAC Reaction |
| spellingShingle | 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 Synthesis of new 1,4-disubstituted 1,2,3-triazoles using the CuAAC reaction and determination of their antioxidant activities Anais da Academia Brasileira de Ciências Antioxidant activity Free radicals 1,2,3-Triazole CuAAC Reaction |
| title | Synthesis of new 1,4-disubstituted 1,2,3-triazoles using the CuAAC reaction and determination of their antioxidant activities |
| title_full | Synthesis of new 1,4-disubstituted 1,2,3-triazoles using the CuAAC reaction and determination of their antioxidant activities |
| title_fullStr | Synthesis of new 1,4-disubstituted 1,2,3-triazoles using the CuAAC reaction and determination of their antioxidant activities |
| title_full_unstemmed | Synthesis of new 1,4-disubstituted 1,2,3-triazoles using the CuAAC reaction and determination of their antioxidant activities |
| title_short | Synthesis of new 1,4-disubstituted 1,2,3-triazoles using the CuAAC reaction and determination of their antioxidant activities |
| title_sort | synthesis of new 1 4 disubstituted 1 2 3 triazoles using the cuaac reaction and determination of their antioxidant activities |
| topic | Antioxidant activity Free radicals 1,2,3-Triazole CuAAC Reaction |
| url | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0001-37652021000500603&tlng=en |
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