Efficient Chemical Synthesis of a Scutellarein Derivative Containing Morpholine Ring

ISSN: 1875-6255 (Online)
ISSN: 1570-1786 (Print)


Volume 11, 10 Issues, 2014


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Letters in Organic Chemistry

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Miguel Yus
Universidad de Alicante Apdo
Alicante
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Efficient Chemical Synthesis of a Scutellarein Derivative Containing Morpholine Ring

Author(s): Qian-Ping Shi, Zhi-Hao Shi, Nian-Guang Li, Yu-Ping Tang, Hao- Tang, Wei Zhang, Min-Zhe Shen, Ze-Xi Dong, Peng-Xuan Zhang, Jian-Ping Yang and Jin-Ao Duan

Affiliation: Jiangsu Collaborative Innovation Center of Chinese Medicinal Resources Industrialization, Nanjing University of Chinese Medicine, Nanjing 210023, P.R. China.

Abstract

Scutellarin (1) [5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl β -D-glucopyranosiduronic acid] is very effective in the clinical treatment of cerebral infarction and coronary heart disease in China. Pharmacokinetic studies showed that scutellarin (1) is readily metabolized to scutellarein (2) [5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-1- benzopyran-4-one] in the intestine by β -glucuronide enzyme prior to absorption. In order to improve the biological activity of scutellarin (1), our group has previously synthesized many scutellarin derivatives based on their in vivo metabolic mechanism. The results showed that morpholine ring substituted at C-7 or C-8 position induced better antioxidant activity, water solubility and anticoagulant activity compared to scutellarin (1). In this paper, an efficient synthetic method for the construction of 5,6,7-trihydroxy-2-[4-[2-(4-morpholinyl)ethoxy]phenyl]-4H-1-benzopyran-4-one (5) is reported. This synthetic route will facilitate the synthesis of scutellarein derivatives containing an amine side chain at the C- 4' position.




Keywords: Scutellarin, metabolite, scutellarein, morpholine, bioavailability.

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Article Details

Volume: 11
Issue Number: 8
First Page: 590
Last Page: 595
Page Count: 6
DOI: 10.2174/1570178611666140421230118
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