Quercetin-3-O-acyl ester and preparation method thereof

A technology of acyl ester and quercetin, applied in the field of chemical chemistry, can solve the problems of no anti-tumor activity, poor stability and the like

Inactive Publication Date: 2012-09-12
ZHENGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these documents do not provide information about the antitumor activity of
PJ.Mulholland et al. (Annals of Oncology, 2001, 12:245-248.) synthesized 3′-(N-carboxymethyl)carbamoyl-3,4′,5,7-tetrahydroxyfl

Method used

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  • Quercetin-3-O-acyl ester and preparation method thereof
  • Quercetin-3-O-acyl ester and preparation method thereof
  • Quercetin-3-O-acyl ester and preparation method thereof

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preparation example Construction

[0031] 2 Preparation of compounds

[0032] 2.17 Synthesis of 3`,4`-O-tribenzylquercetin

[0033] Take 2.44g (4.0mmol) of rutin and dissolve it in 20ml of DMF, add 1.93g (14.0mmol) of anhydrous potassium carbonate and stir, under ice bath conditions, slowly add 1.6ml (14.0mmol) of freshly distilled benzyl chloride dropwise, and slowly heat up After reaching room temperature, the reaction was stirred overnight (about 12 h), and the reaction was complete as detected by TLC. Add glacial acetic acid to adjust the pH of the reaction solution to 6, then add 200ml of distilled water to it, a large amount of precipitation precipitates out, after stirring for 1 hour, solids gather at the bottom of the bottle, and the supernatant is discarded. Add 60ml of 95% ethanol to the precipitate, heat in a water bath until the solid is completely dissolved, add 10ml of concentrated hydrochloric acid at one time, and heat to reflux. After 15 minutes, a yellow precipitate begins to form, and the re...

Embodiment 1

[0035] Embodiment 1: the preparation of quercetin-3-O-acetate (3a)

[0036] Synthesis of 7,3`,4`-O-tribenzylquercetin-3-O-acetate

[0037] Weigh 1.144g (2mmol) tribenzyl quercetin, dissolve it in 40ml of anhydrous dichloromethane, add 0.144g (2.4mmol) acetic anhydride, add DMAP 29mg (0.24mmol) under stirring, stir at room temperature for 5h, TLC The detection response is complete. The reaction solution was washed three times with saturated sodium bicarbonate, dilute hydrochloric acid, and saturated brine, dried over anhydrous sodium sulfate, and the solvent was recovered to obtain a light yellow solid, which was recrystallized with chloroform-methanol and dried to obtain a light yellow solid with a yield of 80% %. 1 H NMR (400MHz, CDCl3) δ12.19 (s, 1H, 5-OH), 7.48-7.30 (m, 17H, Ar-H), 7.01 (d, J=9.1Hz, 1H, 5'-H), 6.48(d, J=2.2Hz, 1H, 8-H), 6.45(d, J=2.2Hz, 1H, 6-H), 5.25(s, 2H, OCH2C6H5), 5.21(s, 2H, OCH2C6H5), 5.13(s, 2H, OCH2C6H5), 2.25(s, 3H, CH3CO-). 13 C NMR(101MHz,C...

Embodiment 2

[0040] Embodiment 2: the preparation of quercetin-3-O-propionate (3b)

[0041] Synthesis of 7,3`,4`-O-tribenzylquercetin-3-O-acrylate

[0042] Weigh 1.144g (2mmol) tribenzyl quercetin, dissolve in 40ml anhydrous dichloromethane, add 0.173g (2.4mmol) acrylic acid, add DMAP 29mg (0.24mmol) under stirring, weigh 0.496g (2.4mmol) ) DCC was dissolved in anhydrous dichloromethane, and the dichloromethane solution of DCC was slowly added dropwise under ice-bath conditions. After the dropwise addition, the temperature was slowly raised to room temperature, and the stirring reaction was continued for 5 h. TLC detected that the reaction was complete. The reaction solution was refrigerated for 1 h, and the generated DCU was removed by filtration. The filtrate was washed three times with saturated sodium bicarbonate, dilute hydrochloric acid, and saturated brine, dried over anhydrous sodium sulfate, and the solvent was recovered to obtain a light yellow solid, which was recrystallized wi...

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Abstract

The invention relates to quercetin-3-O-acyl ester and a preparation method thereof and belongs to the technical field of pharmaceutical chemistry. The preparation method comprises the following steps: taking cheap rutin as a starting raw material and preparing a quercetin-3-O-acyl ester compound through benzylation, hydrolysis under the acidic conditions, esterification, catalytic hydrogenolysis and other reactions. The method has the characteristics of good selectivity, mild reaction condition, high yield, low cost, simplicity and convenience in operation, easiness in industrial production and the like. In addition, the inhibitory effect of the obtained quercetin-3-O-acyl ester on human esophageal squamous carcinoma cells EC9706, human prostatic cancer cells PC-3 and human gastric cancer cells MGC-803 is remarkably superior to that of quercetin; and the quercetin-3-O-acyl ester can be used in the field of foods and medicines and is possible to develop into a new candidate drug for treating tumor.

Description

technical field [0001] The invention belongs to the technical field of biochemistry, and in particular relates to a synthetic method of quercetin derivatives. Background technique [0002] The chemical name of quercetin is 3,5,7,3',4'-pentahydroxyflavone, which belongs to flavonols and exists in the flowers, leaves and fruits of various plants. Such as existing in onions, peppers, apples, grapes and other edible vegetables and fruits; many Chinese herbal medicines such as Sophora japonica, golden buckwheat, dandelion, etc. contain quercetin (Agnes W.Boots, Guido R.M.M.Haenen, Aalt Bast., European Journal of Pharmacology, 2008, 585:325-337; Bushra Sultana, Farooq Anwar., Food Chemistry, 2008, 108:879-884.). Studies have shown that quercetin has the effects of lowering blood pressure, lowering cholesterol, lowering blood fat, anti-aging, anti-virus, and antibacterial. And has a strong anti-oxidation and free radical scavenging function, it can effectively prevent the activat...

Claims

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Application Information

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IPC IPC(8): C07D311/30C07D405/12A61K31/352A61K31/455A61K31/625A61P35/00
Inventor 翟广玉朱玮渠文涛李洪峰周琳
Owner ZHENGZHOU UNIV
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