An efficient one-pot synthesis of polyphenolic amino acids and evaluation of their radical-scavenging activity |
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| Affiliation: | 1. Chemistry Centre, University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal;2. REQUIMTE/LAQV, Department of Chemistry and Biochemistry, Faculty of Science, University of Porto, Rua do Campo Alegre 687, Porto, Portugal;1. University of Florence, Department of Chemistry “Ugo Schiff”, Via della Lastruccia 3-13, I-50019 Sesto Fiorentino, Italy;2. University of Florence, NEUROFARBA Dept., Sezione di Scienze Farmaceutiche, Via Ugo Schiff 6, 50019 Sesto Fiorentino, Florence, Italy;1. Karadeniz Technical University, Department of Chemistry, 61080 Trabzon, Turkey;2. Karadeniz Technical University, Maçka Vocational School, Department of Chemistry and Chemical Processing Technology, 61750 Trabzon, Turkey;3. Recep Tayyip Erdoğan University, Department of Biology, Rize, Turkey;1. Department of Chemistry, Faculty of Science, Ataturk University, 25240 Erzurum, Turkey;2. Department of Biotechnology, Faculty of Science, Bartin University, 74100 Bartin, Turkey;1. University of Florence, NEUROFARBA Dept., Sezione di Scienze Farmaceutiche e Nutraceutiche, Via Ugo Schiff 6, 50019 Sesto Fiorentino, Florence, Italy;2. University of Pisa, Department of Pharmacy, Via Bonanno 6, 56126 Pisa, Italy;3. University of Florence, NEUROFARBA Dept., Sezione di Farmacologia e Tossicologia, Viale Gaetano Pieraccini 6, 50139 Florence, Italy;4. Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS, ENSCM, Université de Montpellier, 240 avenue du Professeur Emile Jeanbrau, 34296 Montpellier Cedex 05, France;1. State Key Laboratory of Biocontrol and Guangdong Provincial Key Laboratory of Plant Resources, School of Life Sciences, Sun Yat-Sen University, Guangzhou 510275, PR China;2. Laboratorio de Nanocelulosa y Biomateriales, Departamento de Ingeniería Química, Biotecnología y Materiales, Facultad de Ciencias Físicas y Matemáticas, Universidad de Chile, Avenida Beauchef 851, Santiago, Chile;3. Department of Marine and Coastal Studies, Madurai Kamaraj University, Madurai 625 021 Tamil Nadu, India;4. Department of Marine Science, Bharathidasan University, Tiruchirappalli, Tamil Nadu 620024, India |
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| Abstract: | 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. |
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| Keywords: | Polyphenolic amino acids Hydroxyphenylglycines Cell-penetrating peptides Ugi reaction diHydroxyphenylglycyl peptides Radical-scavenging activity Oxidation potential |
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