Synthesis and DPPH radical scavenging activity of novel compounds obtained from tyrosol and cinnamic acid derivatives

被引：46

作者：

Barontini, Maurizio ^{[1
]}

Bernini, Roberta ^{[1
]}

Carastro, Isabella ^{[1
]}

Gentili, Patrizia ^{[2
]}

Romani, Annalisa ^{[3
]}

机构：

[1] Univ Tuscia, Dipartimento Sci & Tecnol Agr Foreste Nat & Energ, I-01100 Viterbo, Italy

[2] Univ Roma La Sapienza, Dipartimento Chim, I-00185 Rome, Italy

[3] Univ Roma La Sapienza, IMC CNR Sez Meccanismi Reaz, I-00185 Rome, Italy

来源：

NEW JOURNAL OF CHEMISTRY | 2014年 / 38卷 / 02期

关键词：

STREPTOMYCES-AUREOFACIENS CMUAC130; ONE-POT SYNTHESIS; VIRGIN OLIVE OIL; CONVENIENT SYNTHESIS; MEDIATED HYDROARYLATION; ANTIOXIDANT ACTIVITY; PHENOLIC-COMPOUNDS; OXIDATIVE STRESS; HYDROXYTYROSOL; DIHYDROCOUMARINS;

D O I：

10.1039/c3nj01180a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Tyrosol, a naturally occurring phenolic compound poorly attractive as an antioxidant because of its weak efficacy, was used as starting material to obtain novel compounds. The synthesis is based on a trifluoroacetic acid-mediated hydroarylation of cinnamic esters with tyrosol to produce 4-aryl-3,4-dihydrocoumarins, molecules of biological interest, followed by a basic hydrolysis to give the corresponding ring opening products. Unreported mechanistic investigations confirmed that the first step resulted from an electrophilic aromatic substitution and an intramolecular transesterification. Final products exhibited DPPH radical scavenging activity significantly higher than tyrosol.

引用

页码：809 / 816

页数：8

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