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Method for preparing baicalein

A technology of baicalein and compounds, which is applied in the field of preparing commonly used antiviral and antibacterial anti-inflammatory drugs and medicinal active ingredient baicalein, can solve the problems of high technical conditions, difficulty in production and application, low yield of multi-step reaction, etc., and achieve reaction yield High-efficiency, easy-to-operate effects

Active Publication Date: 2016-01-13
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has high efficiency and basically has the potential for production and application, but its sources of synthetic raw materials are mostly limited, making it difficult to produce and apply
In 2014, Xu, Bei-hua et al. used phloroglucinol as the starting material to obtain chrysin through acetylation and ester condensation reactions, and then performed Ebls oxidation to obtain baicalein (Xu, Bei-hua; Zhou, Hui- yan;Wo,Lian-qun.Synthesis of baicalein,GuangzhouHuagong(2014),42(9),68-69,73), but the technical conditions required for the preparation process of this method are relatively high, even harsh, and the yield of multi-step reaction is very low. Low, only suitable for laboratory preparation, not suitable for production applications at all
In addition, in the same year, Jing, Linlin et al. used chrysin as raw material to prepare baicalein through methylation, bromination, methoxy substitution, demethylation and rearrangement reactions (Jing, Linlin; Fan, Xiaofei; Ma, Huiping; Fan, Pengcheng; Jia, Zhengping.Convenientsynthesis of baicalein, ZhongguoYiyaoGongyeZazhi (2014), 45(10), 916-918), but because the source of chrysin is also very limited, and its price is high, so the efficiency and cost of preparing baicalein by this method also quite high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: The preparation method of this baicalein is as follows:

[0033] (1) Synthesis of Compound 3: Weigh 23.5g (0.25mol) of phenol into a 1000ml round bottom flask, add 300ml of methanol and 130ml of commercially available hydrobromic acid with a concentration of 47% by mass, and then slowly Add 90ml of hydrogen peroxide with a mass percent concentration of 30% dropwise therein, and control the dropping rate so that the temperature of the reaction solution does not exceed 40°C, and the addition is completed in about 1-2 hours. After addition, continue stirring for 1-2 hours, add a little sodium bisulfite, filter after a few minutes, wash the filter cake with a small amount of methanol, press dry, and dry at 70-80°C to obtain a white powdery solid, namely compound 3; Weighing: 82.0g, yield: 98%. 1 HNMR (DMSO): δ9.92(s, 1H), δ7.46(s, 2H).

[0034] (2) Synthesis of Compound 4: Weigh 84.0g (1.5mol) of sodium methoxide into a 1000ml round bottom flask, add 200ml of ...

Embodiment 2

[0042] Example 2: The preparation method of this baicalein is as follows:

[0043] (1) Synthesis of Compound 3: Weigh 23.5g (0.25mol) of phenol into a 1000ml round bottom flask, add 500ml of acetic acid, 80g (0.78mol) of sodium bromide and 20ml (0.40mol) of commercially available 98% concentrated sulfuric acid , then slowly add 90ml of hydrogen peroxide with a mass percentage concentration of 30% to it under vigorous stirring at room temperature, control the rate of addition so that the temperature of the reaction solution does not exceed 45°C, and add it in about 1-2 hours; after the addition, continue to stir for 1- After 2 hours, add a little sodium bisulfite, filter after a few minutes, wash the filter cake with a small amount of distilled water, press dry, and dry at 70-80°C to obtain a white powdery solid, that is, compound 3. Weighing: 82.0g, yield: 99%. 1 HNMR (DMSO): same as step (1) of Example 1 above.

[0044] (2) Synthesis of compound 4: Weigh 84.0g (1.5mol) of...

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Abstract

The invention relates to a method for preparing anti-virus and anti-bacterial inflammatory medicine baicalein. According to the method, phenol serves as a starting material, and a key chalcone intermediate is prepared through bromination, methoxy substitution, Friedel-crafts acylation and aldol condensation; the key intermediate is subjected to oxidative cyclisation and methyl removal reaction, and high-purity baicalein can be prepared. According to the new method, adopted raw reagents are cheap and easy to obtain, the number of synthesis steps is small, reaction operation is easy and convenient, production control is easy, the product yield is high, purity is good, and the method is suitable for production and application of baicalein.

Description

technical field [0001] The invention relates to the fields of organic chemistry and medicinal chemistry, that is, a method for preparing commonly used antiviral, antibacterial and anti-inflammatory drugs and baicalein as a medicinal active ingredient. Background technique [0002] Baicalein, also known as baicalein, English name: Baicalein, chemical name: 5,6,7-trihydroxyflavone. Baicalein is an important medicinal active ingredient in traditional Chinese medicine Scutellaria baicalensis George and Oroxylumindicum. Modified derivatives also show good biological activity and medicinal prospects (Wang, Yu-nong; Jin, Ye-zhi; Dong, Ying-ying; Wu, Ying; Hao, Yu. 14(27), 5365-5369; Yun, Bao-yi; Zhou, Lei; Xie, Kun-peng; Wang, Ye-ju; Xie, Ming-jie. -1592; Kim, KyunHa; Park, Young-Don; Park, Heejin; Moon, Keum-Ok; Ha, Ki-Tae; Baek, Nam-In; - inflammatory agent, European Journal of Pharmacology (2014), 744, 147-156; etc.). [0003] At present, baicalein used in clinical treatment...

Claims

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Application Information

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IPC IPC(8): C07D311/30
CPCC07D311/30
Inventor 杨健王谦崔巍杨波
Owner KUNMING UNIV OF SCI & TECH
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