A New and Practical Synthetic Method for the Synthesis of 6-O-Methyl-scutellarein: One Metabolite of Scutellarin in Vivo

A New and Practical Synthetic Method for the Synthesis of 6-O-Methyl-scutellarein: One Metabolite of Scutellarin in Vivo

Scutellarin (1) has been used for the treatment of angina pectoris, cerebral infarction and coronary heart disease with a large market share in China. Pharmacokinetic studies on scutellarin showed that scutellarin (1) is readily converted into its metabolites in vivo. In this paper, a new and practi...

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Main Authors: Hang Lin, Wei Zhang, Ze-Xi Dong, Ting Gu, Nian-Guang Li, Zhi-Hao Shi, Jun Kai, Cheng Qu, Guan-Xiong Shang, Yu-Ping Tang, Fang Fang, He-Min Li, Jian-Ping Yang, Jin-Ao Duan
Format: Article
Language:English
Published: MDPI AG 2015-04-01
Series:International Journal of Molecular Sciences
Subjects:
6-O-methyl-scutellarein
scutellarin
scutellarein
metabolite
synthesis
Online Access:http://www.mdpi.com/1422-0067/16/4/7587
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spelling doaj-9e0373d35a1643809083503cbacca4a22020-11-24T21:11:58ZengMDPI AGInternational Journal of Molecular Sciences1422-00672015-04-011647587759410.3390/ijms16047587ijms16047587A New and Practical Synthetic Method for the Synthesis of 6-O-Methyl-scutellarein: One Metabolite of Scutellarin in VivoHang Lin0Wei Zhang1Ze-Xi Dong2Ting Gu3Nian-Guang Li4Zhi-Hao Shi5Jun Kai6Cheng Qu7Guan-Xiong Shang8Yu-Ping Tang9Fang Fang10He-Min Li11Jian-Ping Yang12Jin-Ao Duan13National and Local Collaborative Engineering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing 210023, Jiangsu, ChinaNational and Local Collaborative Engineering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing 210023, Jiangsu, ChinaNational and Local Collaborative Engineering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing 210023, Jiangsu, ChinaNational and Local Collaborative Engineering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing 210023, Jiangsu, ChinaNational and Local Collaborative Engineering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing 210023, Jiangsu, ChinaDepartment of Organic Chemistry, China Pharmaceutical University, Nanjing 211198, Jiangsu, ChinaNational and Local Collaborative Engineering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing 210023, Jiangsu, ChinaNational and Local Collaborative Engineering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing 210023, Jiangsu, ChinaNational and Local Collaborative Engineering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing 210023, Jiangsu, ChinaNational and Local Collaborative Engineering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing 210023, Jiangsu, ChinaNational and Local Collaborative Engineering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing 210023, Jiangsu, ChinaNational and Local Collaborative Engineering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing 210023, Jiangsu, ChinaNational and Local Collaborative Engineering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing 210023, Jiangsu, ChinaNational and Local Collaborative Engineering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing 210023, Jiangsu, ChinaScutellarin (1) has been used for the treatment of angina pectoris, cerebral infarction and coronary heart disease with a large market share in China. Pharmacokinetic studies on scutellarin showed that scutellarin (1) is readily converted into its metabolites in vivo. In this paper, a new and practical synthetic method for the synthesis of 6-O-methyl-scutellarein (3) (one metabolite of scutellarin in vivo) is reported. The benzyl bromide was firstly used to selectively replace the acetyl group at C-7 in 7, and was then used to protect the hydroxy groups at C-4' in 10, 6-O-methyl-scutellarein (3) is obtained in high yield through these methods.http://www.mdpi.com/1422-0067/16/4/75876-O-methyl-scutellareinscutellarinscutellareinmetabolitesynthesis
collection DOAJ
language English
format Article
sources DOAJ
author Hang Lin
Wei Zhang
Ze-Xi Dong
Ting Gu
Nian-Guang Li
Zhi-Hao Shi
Jun Kai
Cheng Qu
Guan-Xiong Shang
Yu-Ping Tang
Fang Fang
He-Min Li
Jian-Ping Yang
Jin-Ao Duan
spellingShingle Hang Lin
Wei Zhang
Ze-Xi Dong
Ting Gu
Nian-Guang Li
Zhi-Hao Shi
Jun Kai
Cheng Qu
Guan-Xiong Shang
Yu-Ping Tang
Fang Fang
He-Min Li
Jian-Ping Yang
Jin-Ao Duan
A New and Practical Synthetic Method for the Synthesis of 6-O-Methyl-scutellarein: One Metabolite of Scutellarin in Vivo
International Journal of Molecular Sciences
6-O-methyl-scutellarein
scutellarin
scutellarein
metabolite
synthesis
author_facet Hang Lin
Wei Zhang
Ze-Xi Dong
Ting Gu
Nian-Guang Li
Zhi-Hao Shi
Jun Kai
Cheng Qu
Guan-Xiong Shang
Yu-Ping Tang
Fang Fang
He-Min Li
Jian-Ping Yang
Jin-Ao Duan
author_sort Hang Lin
title A New and Practical Synthetic Method for the Synthesis of 6-O-Methyl-scutellarein: One Metabolite of Scutellarin in Vivo
title_short A New and Practical Synthetic Method for the Synthesis of 6-O-Methyl-scutellarein: One Metabolite of Scutellarin in Vivo
title_full A New and Practical Synthetic Method for the Synthesis of 6-O-Methyl-scutellarein: One Metabolite of Scutellarin in Vivo
title_fullStr A New and Practical Synthetic Method for the Synthesis of 6-O-Methyl-scutellarein: One Metabolite of Scutellarin in Vivo
title_full_unstemmed A New and Practical Synthetic Method for the Synthesis of 6-O-Methyl-scutellarein: One Metabolite of Scutellarin in Vivo
title_sort new and practical synthetic method for the synthesis of 6-o-methyl-scutellarein: one metabolite of scutellarin in vivo
publisher MDPI AG
series International Journal of Molecular Sciences
issn 1422-0067
publishDate 2015-04-01
description Scutellarin (1) has been used for the treatment of angina pectoris, cerebral infarction and coronary heart disease with a large market share in China. Pharmacokinetic studies on scutellarin showed that scutellarin (1) is readily converted into its metabolites in vivo. In this paper, a new and practical synthetic method for the synthesis of 6-O-methyl-scutellarein (3) (one metabolite of scutellarin in vivo) is reported. The benzyl bromide was firstly used to selectively replace the acetyl group at C-7 in 7, and was then used to protect the hydroxy groups at C-4' in 10, 6-O-methyl-scutellarein (3) is obtained in high yield through these methods.
topic 6-O-methyl-scutellarein
scutellarin
scutellarein
metabolite
synthesis
url http://www.mdpi.com/1422-0067/16/4/7587
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