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Letters in Organic Chemistry
ISSN (Print): 1570-1786
ISSN (Online): 1875-6255
VOLUME: 11
ISSUE: 8
DOI: 10.2174/1570178611666140421230118      Price:  $58









Efficient Chemical Synthesis of a Scutellarein Derivative Containing Morpholine Ring

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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
Pages 590-595 (6)
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.
Graphical Abstract:
Keywords:
Scutellarin, metabolite, scutellarein, morpholine, bioavailability.
Affiliation:
Jiangsu Collaborative Innovation Center of Chinese Medicinal Resources Industrialization, Nanjing University of Chinese Medicine, Nanjing 210023, P.R. China.