An efficient one-pot synthesis of polyphenolic amino acids and evaluation of their radical-scavenging activity

• Type: Article in International Scientific Journal
• Date: 2019

Authors

Monteiro, LS (Author) Other; Fatima Paiva Martins (Author) FCUP; Oliveira, S (Author) Other; Machado, I (Author) Other; Costa, M (Author) Other

Journal

Title: Bioorganic Chemistry

Vol. 89

ISSN: 0045-2068

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 5 Citations

Scopus - 6 Citations

Other information

Authenticus ID: P-00Q-JSC

DOI: 10.1016/j.bioorg.2019.102983

Abstract (EN): 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.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 8