Convenient Synthesis of 1-Aryl-dihydroxyisochromans Exhibiting Antioxidant Activity

被引：15

作者：

Bernini, Roberta ^{[1
]}

Crisante, Fernanda ^{[1
]}

Fabrizi, Giancarlo ^{[2
]}

Gentili, Patrizia ^{[3
]}

机构：

[1] Univ Tuscia, DAFNE, I-01100 Viterbo, Italy

[2] Univ Roma La Sapienza, Dept Drug Chem & Technol, I-00185 Rome, Italy

[3] Univ Roma La Sapienza, Dept Chem, IMC CNR Sect Mech React, I-00185 Rome, Italy

来源：

CURRENT ORGANIC CHEMISTRY | 2012年 / 16卷 / 08期

关键词：

Antioxidants; 1-aryl-dihydroxyisochromans; Aromatic hydroxylation; Catecholic compounds; Dimethyl carbonate (DMC); DPPH radical assay; 2-iodoxybenzoic acid (IBX); oxa-Pictet-Spengler reaction; OXA-PICTET-SPENGLER; DIMETHYL-CARBONATE; ISOCHROMANS; PHENOLS; FLAVONOIDS; HYDROXY-1-ARYL-ISOCHROMANS; HYDROXYTYROSOL; DERIVATIVES; OXIDATION; LIGNIN;

D O I：

10.2174/138527212800194700

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several 1-aryl-hydroxy and dihydroxyisochromans were synthesized by a two-steps procedure based on the oxa-Pictet-Spengler reaction performed for the first time in dimethyl carbonate (DMC) from phenethyl alcohols and substituted benzaldehydes followed by the regioselective aromatic hydroxylation/oxidative aromatic demethylation with 2-iodoxybenzoic acid (IBX)/sodium dithionite (Na2S2O4) system. Some of them showed a novel pattern of hydroxylation degree into A ring. All synthesized isochromans were tested about their radical scavenging activity by 2,2-diphenyl-2-picrylhydrazyl radical (DPPH center dot) method. Experimental results showed that dihydroxyisochromans were more active than the corresponding phenolic or guaiacolic parent compounds confirming the key role of the catecholic moiety for the antioxidant activity.

引用

页码：1051 / 1057

页数：7

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