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

ABSTRACT: 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 I₂.

SUBMITTER: Teng Q

PROVIDER: S-EPMC6664384 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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

Teng Qiaoqiao Q Zhu Xinhui X Guo Qianqian Q Jiang Weihua W Liu Jiang J Meng Qi Q

Beilstein journal of organic chemistry 20190715

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 iodid ...[more]

PMID: 31435439

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