Astilbin derivatives and preparation method thereof
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A technology of fucoside derivatives and astilbin, applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve problems such as limited effect, and achieve the effect of improving bioavailability
Active Publication Date: 2016-11-09
CHENGDU UNIV
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Problems solved by technology
At present, pharmacological methods are used to improve the bioavailability of astilbin, but the effect is still very limited
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Embodiment 1
[0027] Embodiment 1: the preparation of compound AB-S
[0028] Add 1.0g of raw material AB, 3mL of N,N-dimethylformamide into the single-necked bottle to dissolve, add 2.37mL of Bian bromide, 2.7g of anhydrous K 2 CO 3 , Stir the reaction at 45°C for 3h. After the reaction, add 30mL water to the system, extract with ethyl acetate (20mL×3), that is, extract 3 times with 20mL each time; wash the organic phase with dilute hydrochloric acid (15mL×3), wash with water (20mL×3), and concentrate under reduced pressure To dryness, 0.65 g of light yellow solid was obtained.
Embodiment 2
[0029] Embodiment 2: the preparation of compound AB-D
[0030] Add 1.0g of raw material AB, 4mL of N,N-dimethylformamide into the single-necked bottle to dissolve, add 1.85mL of Bian bromide, 2.1g of anhydrous K 2 CO 3 , Stir the reaction at 25°C for 3h. After the reaction was completed, 30 mL of water was added to the system, extracted with ethyl acetate (20 mL×3), the organic phase was washed with dilute hydrochloric acid (15 mL×3), washed with water (20 mL×3), and concentrated to dryness under reduced pressure to obtain a light yellow solid 0.53 g.
Embodiment 3
[0031] Embodiment 3: the preparation of compound AB-S-1 (glucose derivative)
[0032] Add 1.0 g AB-S, 0.31 g bromoglucose, 10 mL CH 2 Cl 2 dissolved, adding anhydrous K 2 CO 3 1.0g, reflux at 50°C for 4h. After the reaction was complete, the reaction solution was spin-dried, then 30 mL of water was added, extracted with ethyl acetate (30 mL×3), washed with dilute hydrochloric acid (15 mL×3), and concentrated to dryness under reduced pressure to obtain 0.61 g of a light yellow solid.
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Abstract
The invention relates to astilbin derivatives and a preparation method thereof and belongs to the technical field of fine chemical engineering. Astilbin is used as a raw material, a C-5 hydroxyl exposed single-hydroxyl intermediate AB-S and a C-5 and C-3' hydroxyl exposed double-hydroxyl intermediate AB-D are respectively prepared by controlling the molar ratio of benzyl bromide to the astilbin. The intermediates AB-S and AB-D respectively react with halogenated sugar, and the astilbin derivatives AB-S-X and AB-D-X are respectively prepared through deprotection. According to the astilbin derivatives and the preparation method of the astilbin derivatives, the bioavailability of the astilbin is improved by conducting selective protection and deprotection on phenolic hydroxyl groups and rhamnose hydroxyls, introducing monosaccharides or disaccharides to C-5 of flavanone parent nucleuses and introducing monosaccharides or disaccharides to C-5 and C-3'.
Description
technical field [0001] The invention belongs to the field of fine chemical industry, and specifically relates to astilbin derivatives and a preparation method thereof. Background technique [0002] Astilbin (AB) is a dihydroflavonoid compound with two hydroxyl structures of polyphenols and rhamnose, and is an active ingredient of traditional Chinese medicines such as Smilax smilax and Saffron. Studies have shown that astilbin has a variety of biological activities, including inhibition of coenzyme A reductase, inhibition of aldose reductase, anti-edema, and selective immunosuppressive effects. Astilbin is easily soluble in organic solvents such as methanol and ethanol, and is very slightly soluble in water, with a water solubility of 250ug / mL at 25°C; the bioavailability of astilbin in rats is only 0.066%, and it is a compound with poor oral absorption . Currently, pharmacological methods are used to improve the bioavailability of astilbin, but the effect is still very lim...
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