Efficient Chemical Synthesis of a Scutellarein Derivative Containing Morpholine Ring
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-
Keywords: Scutellarin, metabolite, scutellarein, morpholine, bioavailability.
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