Synthesis of 9-O-arylated berberines via copper-catalyzed CAr-O coupling reactions

被引：9

作者：

Teng, Qiaoqiao ^{[1
]}

Zhu, Xinhui ^{[1
]}

Guo, Qianqian ^{[1
]}

Jiang, Weihua ^{[1
]}

Liu, Jiang ^{[1
]}

Meng, Qi ^{[1
]}

机构：

[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 15卷

关键词：

arylation; berberines; cross-coupling; copper; lipophilicity; structural modification; BIOLOGICAL EVALUATION; DERIVATIVES; DESIGN; PROTOBERBERINE; ANALOGS; SERIES;

D O I：

10.3762/bjoc.15.161

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Berberine is a widely used antimicrobial agent in clinic. However, a high dosage is often required due to its low lipophilicity and bioavailability. The current study explores the structural modifications of berberines with potentially lipophilic aryl groups to address this problem. A series of 15 9-O-aryl-substituted berberines (3a-o) and one 9-O-phenylene-bridged berberine dimer (5) was synthesized by copper-catalyzed cross-coupling of tetrahydroberberrubine and aryl iodides, followed by oxidation with I-2.

引用

页码：1575 / 1580

页数：6

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