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Int. J. Mol. Sci. 2015, 16(4), 7587-7594; doi:10.3390/ijms16047587

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

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1
National and Local Collaborative Engineering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing 210023, Jiangsu, China
2
Jiangsu Key Laboratory for High Technology Research of TCM Formulae, Nanjing University of Chinese Medicine, Nanjing 210023, Jiangsu, China
3
Jiangsu Collaborative Innovation Center of Chinese Medicinal Resources Industrialization, Nanjing University of Chinese Medicine, Nanjing 210023, Jiangsu, China
4
Department of Organic Chemistry, China Pharmaceutical University, Nanjing 211198, Jiangsu, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Bing Yan
Received: 11 December 2014 / Revised: 15 March 2015 / Accepted: 17 March 2015 / Published: 3 April 2015
(This article belongs to the Section Biochemistry, Molecular and Cellular Biology)
View Full-Text   |   Download PDF [691 KB, uploaded 3 April 2015]   |  

Abstract

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. View Full-Text
Keywords: 6-O-methyl-scutellarein; scutellarin; scutellarein; metabolite; synthesis 6-O-methyl-scutellarein; scutellarin; scutellarein; metabolite; synthesis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Lin, H.; Zhang, W.; Dong, Z.-X.; Gu, T.; Li, N.-G.; Shi, Z.-H.; Kai, J.; Qu, C.; Shang, G.-X.; Tang, Y.-P.; Fang, F.; Li, H.-M.; Yang, J.-P.; Duan, J.-A. A New and Practical Synthetic Method for the Synthesis of 6-O-Methyl-scutellarein: One Metabolite of Scutellarin in Vivo. Int. J. Mol. Sci. 2015, 16, 7587-7594.

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