Cu–Al mixed oxide-catalysed multi-component synthesis of gluco- and allofuranose-linked 1,2,3-triazole derivatives
| Autor: | Álvaro C. Rodríguez-Sánchez, Leticia Lomas-Romero, Yarisel Ruiz Almazan, Guillermo E. Negrón-Silva, Alma Sánchez-Eleuterio, Claudia Negrón-Lomas, Ricardo Corona-Sánchez |
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| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Sodium ascorbate
1 2 3-Triazole Triazole biological activity 010402 general chemistry multi-component reaction 01 natural sciences chemistry.chemical_compound cu–al mixed oxide Multi-component reaction lcsh:Science Multidisciplinary biology 010405 organic chemistry Chemistry Aspergillus niger Regioselectivity biology.organism_classification Combinatorial chemistry Cycloaddition glycoconjugates 0104 chemical sciences Mixed oxide lcsh:Q 1 2 3-triazole Research Article |
| Zdroj: | Royal Society Open Science, Vol 7, Iss 7 (2020) Royal Society Open Science |
| ISSN: | 2054-5703 |
| DOI: | 10.1098/rsos.200290 |
| Popis: | A series of carbohydrate-linked 1,2,3-triazole derivatives were synthesized in good yields from glucofuranose and allofuranose diacetonides using as key step a three-component 1,3-dipolar azide–alkyne cycloaddition catalysed by a Cu–Al mixed oxide. In this multi-component reaction, Cu–Al mixed oxide/sodium ascorbate system serves as a highly reactive, recyclable and efficient heterogeneous catalyst for the regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles. The reported protocol has significant advantages over classical CuI/ N , N -diisopropylethylamine (DIPEA) or CuSO 4 /sodium ascorbate conditions in terms of efficiency and reduced synthetic complexity. In addition, the selective deprotection of synthesized di- O -isopropylidene derivatives was also carried out leading to the corresponding mono- O -isopropylidene products in moderate yields. Some of the synthesized triazole glycoconjugates were tested for their in vitro antimicrobial activity using the disc diffusion method against Gram-positive bacteria ( Staphylococcus aureus and Bacillus subtilis ), Gram-negative bacteria ( Escherichia coli and Pseudomonas aeruginosa ), as well as fungus ( Aspergillus niger ) and yeast ( Candida utilis ). The results revealed that these compounds exhibit moderate to good antimicrobial activity mainly against Gram-negative bacteria. |
| Databáze: | OpenAIRE |
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