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Synthesis of Quercetin‑3‑o‑Acetate and Its Application in Antitumor

A technology of quercetin and its use, which is applied in the chemical field and can solve the problems of unfavorable industrial production and low yield

Active Publication Date: 2017-10-13
西安天一生物技术股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the productive rate of this method is low, is unfavorable for industrialized production

Method used

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  • Synthesis of Quercetin‑3‑o‑Acetate and Its Application in Antitumor
  • Synthesis of Quercetin‑3‑o‑Acetate and Its Application in Antitumor
  • Synthesis of Quercetin‑3‑o‑Acetate and Its Application in Antitumor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1 Synthesis of the compound quercetin-3-O-ethyl acetate

[0018] 1 Experimental instruments and materials

[0019] 1.1 Instruments and equipment

[0020] Rotary evaporator: RE-52AA, Shanghai Yarong Biochemical Instrument Factory; Circulating water vacuum pump: SHZ-(Ⅲ) type, Tianjin Huaxin Instrument Factory;

[0021] Constant temperature magnetic stirrer: 85-2 type, Shanghai Sile Instrument Co., Ltd.; infrared spectrometer, iS10FT-IR type, Nicholas, USA; superconducting nuclear magnetic resonance apparatus, 400MHz type, Bruker (DMSO-d 6 or CDCl 3 For solvent, TMS is internal standard); Hydrogenation unit:

[0022] 1.2 Drugs and reagents

[0023] Rutin: purity > 95%, Henan Pingyu Xinxing Biochemical Co., Ltd.; ethyl bromoacetate: purity 98%, Shanghai Jingchun Reagent Co., Ltd.; benzyl bromide: 99%, Shanghai Jingchun Reagent Co., Ltd.; palladium carbon : 10% Pd, Shanghai Jingchun Reagent Co., Ltd.; N,N-dimethylformamide, ethyl acetate, anhydrous potassium car...

Embodiment 2

[0031] Example 2 Synthesis of the compound quercetin-3-O-methyl acetate

[0032] 1.1 Synthesis of 3′,4′,7-O-tribenzylquercetin-3-O-methyl acetate (4)

[0033] Dissolve 2.86g (5mmol) of dry compound 1 in 60ml DMF, add anhydrous K 2 CO 3 900mg (6.5mmol), stirred at room temperature for 30min, then slowly added dropwise a solution of 735mg (5.5mmol) methyl bromoacetate in DMF (20ml), reacted at room temperature for 2h, TLC monitored the completion of the reaction. Adjust the pH to 6-7 with glacial acetic acid, then extract with ethyl acetate / water (100 / 80ml), wash with saturated brine, dry the ester layer with anhydrous sodium sulfate overnight, filter, concentrate under reduced pressure, pass through a short column (acetone / petroleum ether 1:4) to obtain 2.76g of compound 4, yield 85.7%. 1 H NMR (400MHz, CDCl 3 )δ12.49 (s, 1H, 5-OH), 7.89 (d, J = 2.1Hz, 1H), 7.74 (dd, J = 8.6, 2.1Hz, 1H), 7.54–7.31 (m, 15H), 7.05 (d, J=8.7Hz, 1H), 6.47(dd, J=20.1, 2.2Hz, 2H), 5.30(d, J=5....

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Abstract

Quercetin has the pharmacological activities of eliminating phlegm, relieving cough, relieving asthma, lowering blood pressure, resisting cancer, resisting viruses, resisting bacteria, resisting oxidation and the like. The structure of quercetin is modified and transformed by utilizing a chemical method, so as to hopefully improve the bioavailability of quercetin and strengthen the pharmacological activities of quercetin. Quercetin selectively protected by benzyl bromide is utilized, and a Williamson reaction is utilized to introduce acetate to the third site of quercetin, so as to synthesize a series of quercetin-3-O-acetate derivants. An MTT method proves that compared with quercetin, the compound can obviously inhibit growth of esophagus cancer cells, and is a novel anti-tumor candidate compound with great potential.

Description

technical field [0001] The invention relates to the field of chemistry, in particular to a class of novel quercetin derivatives and a synthesis method thereof. Background technique [0002] Quercetin (quercetin, 3, 3ˊ, 4ˊ, 5, 7 pentahydroxyflavone) is a flavonoid compound widely distributed in the plant kingdom, and many daily edible vegetables, fruits and Chinese herbal medicines are rich in quercetin, such as Onions, apples, strawberries, pagoda rice, Panax notoginseng, red wine, green tea, dark tea, etc. The average content of quercetin is about 6mg / kg, and it can reach 85.6mg / kg in some vegetables with high content, such as onions. Studies have shown that quercetin has a wide range of pharmacological effects such as anti-tumor, anti-oxidation, anti-asthma, anti-inflammatory, anti-allergic, antispasmodic, lowering blood pressure, dilating coronary arteries, lowering blood fat, anti-arrhythmia, and anti-platelet aggregation. A natural flavonoid compound with great medici...

Claims

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Application Information

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IPC IPC(8): C07D311/30A61K31/352A61P35/00
CPCC07D311/30
Inventor 田廷科孙伟霞仝雷张景亮翟广玉
Owner 西安天一生物技术股份有限公司
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