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Scutellarein derivative and preparation method and application thereof

A technology of scutellarin and derivatives, applied in the field of scutellarin derivatives and their preparation, can solve the problems of low bioavailability, limited preparation and clinical application, fast metabolism in vivo and the like

Active Publication Date: 2017-06-23
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although scutellarin has achieved good results in clinical application, its preparation and clinical application are limited due to defects such as poor solubility, low bioavailability, and rapid metabolism in the body.

Method used

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  • Scutellarein derivative and preparation method and application thereof
  • Scutellarein derivative and preparation method and application thereof
  • Scutellarein derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1 10-Hydroxy-7-(4'-hydroxyphenyl)-2,3-dihydro-9H-{[1,4]-dioxo[2,3-g]benzo}pyran- Preparation of 9-keto (compound 2)

[0046] Dissolve scutellarein (286.24mg, 1mmol) in 5mL of anhydrous DMF, add potassium carbonate (207.3mg, 1.5mmol) and dibromoethane (129.87μL, 1.5mmol) at room temperature, N 2 Under protection, react at 110°C for 2h. After the reaction, the reaction liquid was poured into 40 mL of water, a large amount of yellow solids were precipitated, filtered with suction, and the filter cake was recrystallized with methanol to obtain 90 mg of yellow powder with a yield of 29%. Identified as 10-hydroxy-7-(4'-hydroxyphenyl)-2,3-dihydro-9H-{[1,4]-dioxo[2,3-g]benzo}pyran- 9-keto.

[0047]

[0048] ESI-MS m / z: 335.1[M+Na] + , 313.1[M+H] + , 311.1[M-H] - , with a relative molecular mass of 312.

[0049] 1 H-NMR (300MHz, DMSO-d 6 )δ13.03(s, 1H, 10-OH), 10.39(s, 1H, 4'-OH), 7.93(d, 2H, J=8.6Hz, 2', 6'-OH), 6.91(d, 2H, J=8.6Hz, 3', 5'-OH), 6.81(s, 1H, ...

Embodiment 2

[0050] Example 2 10-Hydroxy-7-(4'-epoxypropylphenyl)-2,3-dihydro-9H-{[1,4]-dioxo[2,3-g]benzo} Preparation of pyran-9-one (compound 3)

[0051] Compound 2 (120.00mg, 0.4mmol) was dissolved in 4mL DMF, and potassium carbonate (110.56mg, 0.8mmol) and potassium iodide (66.40mg, 0.4mmol) were added sequentially, and chlorinated propylene oxide (37.63μL, 0.48mmol), reacted at 85°C for 5h. After the reaction was completed, it was cooled to room temperature, and the reaction solution was extracted with 40 mL of ethyl acetate, washed 3 times with saturated brine, 20 mL each time, the organic layer was dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The product was separated and purified by silica gel column chromatography, washed with The stripping agent was dichloromethane to obtain 56.00 mg of yellow powder with a yield of 38.00%. Identified as 10-hydroxy-7-(4'-epoxypropylphenyl)-2,3-dihydro-9H-{[1,4]-dioxo[2,3-g]benzo} Pyran-9-one.

[...

Embodiment 3

[0055] Example 3 10-Hydroxy-7-(4'-(2-oxo-2-phenylethoxy)phenyl)-2,3-dihydro-9H-{[1,4]-dioxo Preparation of [2,3-g]benzo}pyran-9-one (compound 4)

[0056] Compound 2 (80.00mg, 0.26mmol) was dissolved in 3mL of anhydrous DMF, potassium carbonate (70.87mg, 0.51mmol) and potassium iodide (43.16mg, 0.26mmol) were added sequentially, and 2-bromoacetophenone was added after reacting at room temperature for 30min (61.37mg, 0.31mmol), react at room temperature for 12h. After the reaction was completed, the reaction liquid was extracted with 40 mL of ethyl acetate, washed with saturated brine three times, 20 mL each time, the organic layer was dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The product was separated and purified by silica gel column chromatography, and the eluent Petroleum ether-dichloromethane (1:20) to obtain 56.00 mg of a light yellow powder with a yield of 50.45%. Identified as 10-hydroxy-7-(4'-(2-oxo-2-phenylethoxy)phen...

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Abstract

The invention discloses a scutellarein derivative shown in a formula I, a preparation method of the scutellarein derivative, and application of the scutellarein derivative in preparing anti-tumor drugs. The preparation method comprises the following steps of using scutellarein as an initiating raw material, and synthesizing a series of scutellarein derivatives with an A ring benzodioxane structure, a B ring 4apostrophe-position connected lipid-soluble group and a water-soluble group. The preparation method has the advantages that the synthesizing method is simple, and the operability and reaction yield rate are better. The scutellarein derivative has the advantages that the activity for inhibiting proliferation of multiple tumor cells is realized, and the activity of the scutellarein derivative is better than or equivalent to the activity of scutellarein; the scutellarein derivative is expected to develop into the anti-tumor drugs. (The formula I is shown in the description).

Description

technical field [0001] The invention belongs to the field of drug synthesis, and relates to scutellarein derivatives and their preparation methods and applications, in particular to a type of A ring with a benzodioxane structure, and the 4' position of the B ring is connected with a fat-soluble group and a water-soluble group The scutellarein derivative and its preparation method and application. Background technique [0002] Malignant tumor is also known as cancer. Cancer has become the second largest killer of human life, after cardiovascular disease. Although the average life span of human beings is prolonged, the threat of malignant tumor to human health is becoming more and more obvious. The incidence of cancer in the world is increasing every year. Incrementally, about 7.6 million people die of cancer every year in the world, and more than 10.1 million people suffer from malignant tumors. Cancer has now become one of the common causes of human death. Chemoprevention o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04A61P35/00
CPCC07D493/04
Inventor 冯锋曲玮郝艳峰柳文媛徐健关丽蒋学阳李凌飞
Owner CHINA PHARM UNIV
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