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Method for synthesizing isoliquiritigenin

A technology of isoliquiritigenin and aldol condensation, which is applied in the fields of chemical instruments and methods, preparation of organic compounds, carbon-based compounds, etc., to achieve the effect of simple method, mild reaction conditions, and easy-to-obtain raw materials

Inactive Publication Date: 2010-02-17
NORTHEAST FORESTRY UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among them, patent 200410065383 did not protect the hydroxyl group of the raw material, while patent 200810196922 only protected the hydroxyl group of a raw material 2,4-dihydroxyacetophenone, but after experiments, it was found whether the hydroxyl group of another raw material 4-hydroxybenzaldehyde Protection has an important effect on the yield of synthetic isoliquiritigenin

Method used

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  • Method for synthesizing isoliquiritigenin

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Experimental program
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Effect test

Embodiment 1

[0025] (1) Hydroxyl protection of 4-hydroxybenzaldehyde: add 3.63g of 4-hydroxybenzaldehyde and 0.52g of pyridinium p-toluenesulfonate into a round bottom flask, add dichloromethane and stir well, slowly add 4.2ml of 3,4-bis Hydropyran, then stirred at 30°C, detected by TLC. After 5 hours, the reaction was completed. The solvent in the system was evaporated under reduced pressure, the residue was diluted, washed with saturated brine, and the organic phase was dried, and the solvent was evaporated under reduced pressure to obtain 5.27 g of an oily product with a yield of 86%.

[0026] (2) 4-hydroxyl protection of 2,4-dihydroxyacetophenone: 6.39g2,4-dihydroxyacetophenone and 0.36g pyridinium p-toluenesulfonate were added to the round bottom flask, and dichloromethane was added to stir Uniformly, slowly add 5.70ml of 3,4-dihydropyran, then stir at 30°C for 4h, add 2.4g of sodium bicarbonate, continue to stir for 4h, filter off the sodium bicarbonate, and concentrate the filtrate ...

Embodiment 2

[0034] (1) Hydroxyl protection of 4-hydroxybenzaldehyde: 3.89g 4-hydroxybenzaldehyde and 0.56g pyridinium p-toluenesulfonate were added to a round bottom flask, chloroform was added and stirred evenly, and 3.62ml chloromethylformazol was slowly added ether, then stirred at 35°C and detected by TLC. After 4 hours, the reaction was completed. The solvent in the system was evaporated under reduced pressure, the residue was diluted, washed with saturated brine, and the organic phase was dried, and the solvent was evaporated under reduced pressure to obtain 5.26 g of an oily product with a yield of 80%.

[0035] (2) 4-hydroxyl protection of 2,4-dihydroxyacetophenone: 4.14g2,4-dihydroxyacetophenone and 0.23g pyridinium p-toluenesulfonate were added to the round bottom flask, and chloroform was added to stir Evenly, slowly add 3.07ml of chloromethyl methyl ether, then stir at 35°C for 3h, add 1.55g of sodium bicarbonate, continue to stir for 4h, filter out the sodium bicarbonate, and...

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Abstract

The invention relates to a method for synthesizing isoliquiritigenin, comprising the following steps: using 4-hydroxy benzaldehyde and 2,4-dihydroxyacetophenone as raw materials; and carrying out hydroxyl protection, aldol condensation and dehydroxylation protective reaction to obtain the isoliquiritigenin. The method is simple, and the raw materials have low cost and high yield and are easy to obtain.

Description

technical field [0001] The invention relates to a method for synthesizing isoliquiritigenin, which belongs to the field of organic synthesis. Background technique [0002] Isoliquiritigenin is named after the dry roots and rhizome extracts of Glycyrrhiza uralensis Fisch., Glycyrrhiza inflate Bat. or Glycyrrhiza glabra L., which are leguminous plants. [0003] Isoliquiritigenin (ISL) is an important chalcone compound in licorice, which has biological activities such as anti-tumor, anti-virus, anti-free radical, and inhibition of lipid peroxidation. Among them, the anti-tumor effect is a research hotspot in recent years. Studies have found that isoliquiritigenin can inhibit the induction and metastasis of colon cancer and other tumors, induce breast cancer, gastric cancer, melanoma and other cell apoptosis, and inhibit prostate cell proliferation. In addition, isoliquiritigenin can also inhibit the immunodeficiency virus HIV, and it is expected to be developed into an effecti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/835C07C45/74
Inventor 付玉杰祖元刚马永婷骆浩孔羽李双明李庆勇顾成波
Owner NORTHEAST FORESTRY UNIVERSITY
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