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https://hdl.handle.net/1822/72832
Título: | An efficient one-pot synthesis of polyphenolic amino acids and evaluation of their radical-scavenging activity |
Autor(es): | Monteiro, Luís S. Paiva-Martins, Fátima Oliveira, Sandra Machado, Inês Costa, Marlene |
Palavras-chave: | Polyphenolic amino acids Hydroxyphenylglycines Cell-penetrating peptides Ugi reaction diHydroxyphenylglycyl peptides Radical-scavenging activity Oxidation potential |
Data: | 2019 |
Editora: | Elsevier 1 |
Revista: | Bioorganic Chemistry |
Citação: | Monteiro, L. S., Paiva-Martins, F., Oliveira, S., et al.(2019). An efficient one-pot synthesis of polyphenolic amino acids and evaluation of their radical-scavenging activity. Bioorganic chemistry, 89, 102983 |
Resumo(s): | A simple and efficient procedure for the synthesis of N-acyl 4-hydroxy, 4-hydroxy-3-methoxy and 3,4-dihydroxy phenylglycine amides by a strategy based on the multicomponent Ugi reaction is proposed. Hydroxybenzaldehyde derivatives were reacted with 4-methoxybenzylamine, cyclohexyl isocyanide and benzoic acid or 2-naphthylacetic acid to give Ugi adducts that were treated with trifluoroacetic acid yielding N-acyl hydroxyphenylglycine amides in good yields. The same procedure using as acid component protocatechuic acid or hydrocaffeic acid gave N-catechoyl 3,4-dihydroxyphenylglycine amides. The use of N-benzyloxycarbonylglycine as acid component allowed the preparation of a 3,4-dihydroxyphenylglycyl dipeptide derivative. Radical-scavenging activity studies of the polyphenolic amino acid derivatives showed a sharp increase in activity with the increase in number of hydroxyl or catechol groups present. Cyclic voltammetry experiments established a correlation between oxidation peak potentials and the radical-scavenging activity. |
Tipo: | Artigo |
URI: | https://hdl.handle.net/1822/72832 |
DOI: | 10.1016/j.bioorg.2019.102983 |
ISSN: | 0045-2068 |
Versão da editora: | https://www.sciencedirect.com/science/article/pii/S0045206819303001 |
Arbitragem científica: | yes |
Acesso: | Acesso aberto |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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2019-Bioorganic Chemistry.pdf | 927,24 kB | Adobe PDF | Ver/Abrir |