Synthesis of 9-O-arylated berberines via copper-catalyzed C(Ar)–O coupling reactions

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...

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Autores principales: Teng, Qiaoqiao, Zhu, Xinhui, Guo, Qianqian, Jiang, Weihua, Liu, Jiang, Meng, Qi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2019
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6664384/
https://www.ncbi.nlm.nih.gov/pubmed/31435439
http://dx.doi.org/10.3762/bjoc.15.161
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author Teng, Qiaoqiao
Zhu, Xinhui
Guo, Qianqian
Jiang, Weihua
Liu, Jiang
Meng, Qi
author_facet Teng, Qiaoqiao
Zhu, Xinhui
Guo, Qianqian
Jiang, Weihua
Liu, Jiang
Meng, Qi
author_sort Teng, Qiaoqiao
collection PubMed
description 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).
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spelling pubmed-66643842019-08-21 Synthesis of 9-O-arylated berberines via copper-catalyzed C(Ar)–O coupling reactions Teng, Qiaoqiao Zhu, Xinhui Guo, Qianqian Jiang, Weihua Liu, Jiang Meng, Qi Beilstein J Org Chem Full Research Paper 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). Beilstein-Institut 2019-07-15 /pmc/articles/PMC6664384/ /pubmed/31435439 http://dx.doi.org/10.3762/bjoc.15.161 Text en Copyright © 2019, Teng et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Teng, Qiaoqiao
Zhu, Xinhui
Guo, Qianqian
Jiang, Weihua
Liu, Jiang
Meng, Qi
Synthesis of 9-O-arylated berberines via copper-catalyzed C(Ar)–O coupling reactions
title Synthesis of 9-O-arylated berberines via copper-catalyzed C(Ar)–O coupling reactions
title_full Synthesis of 9-O-arylated berberines via copper-catalyzed C(Ar)–O coupling reactions
title_fullStr Synthesis of 9-O-arylated berberines via copper-catalyzed C(Ar)–O coupling reactions
title_full_unstemmed Synthesis of 9-O-arylated berberines via copper-catalyzed C(Ar)–O coupling reactions
title_short Synthesis of 9-O-arylated berberines via copper-catalyzed C(Ar)–O coupling reactions
title_sort synthesis of 9-o-arylated berberines via copper-catalyzed c(ar)–o coupling reactions
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6664384/
https://www.ncbi.nlm.nih.gov/pubmed/31435439
http://dx.doi.org/10.3762/bjoc.15.161
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