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Flavone derivative for treating tumor and application thereof

A technology of derivatives and flavonoids, applied in the field of novel flavonoid derivatives and their pharmacologically acceptable salts, hydrates or solvates, can solve the problems of low bioavailability and poor solubility in water, and achieve good anti-tumor effects. Activity, high solubility, broad anti-cancer effect

Pending Publication Date: 2020-09-04
SICHUAN FUSHENGYUAN TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the drug active ingredient Acladine has the disadvantages of poor solubility in water and very low bioavailability for oral administration. In order to solve the above problems, the present invention modifies the structure of dehydrated icariin to obtain a new drug with high efficiency and low toxicity. A generation of flavonoid antineoplastic drugs

Method used

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  • Flavone derivative for treating tumor and application thereof
  • Flavone derivative for treating tumor and application thereof
  • Flavone derivative for treating tumor and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] The synthesis of embodiment 1 compound 35

[0061]

[0062]Weigh 9g of compound 25 and dissolve it in 60mL of dichloromethane, add 25mL of 33% hydrobromic acid in acetic acid solution, react at room temperature for 2 hours, TLC monitors that the reaction is complete, pour it into 50mL of water, extract with dichloromethane (50mL×3), and combine The organic layer was washed once with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, filtered, concentrated, and recrystallized with a mixed solvent of petroleum ether / ethyl acetate 10 / 1 to obtain 8.2 g of compound 26 with a yield of 86.7%.

[0063] Dissolve 8.2g of compound 26 in 40mL of dry DMSO, add 1.56g of sodium azide, stir at room temperature for 1 hour, TLC monitors that the reaction is complete, pour it into 100mL of water, extract with ethyl acetate (50mL×3), combine the organic layers and use After drying over anhydrous sodium sulfate, filtering, and concentrating, 5.8 g of compound 27 was obtai...

Embodiment 2

[0071] The synthesis of embodiment 2 compound 39

[0072]

[0073] Weigh 18g of compound 25 and dissolve it in 150mL of dichloromethane, add 6.3g of bromoethanol and 8.7mL of boron trifluoride diethyl ether, and react overnight at room temperature. Saturated sodium bicarbonate was added until no gas was generated, extracted three times with DCM, the organic layers were combined and dried, concentrated, and column chromatography gave 10 g of compound 36, with a yield of 47.7%.

[0074] 10 g of compound 36 was weighed and dissolved in 150 mL of DMF, and 2.86 g of sodium azide was added. React overnight at 60°C. TLC monitored the completion of the reaction. Cool to room temperature, add an appropriate amount of water, extract twice with ethyl acetate (100mL×3), concentrate to remove several layers and a small amount of residual DMF, add an appropriate amount of ethanol to precipitate a solid, and filter to obtain 6.9g of product 37, yield 75.2%.

[0075] Weigh 1g of compoun...

Embodiment 3

[0078] The synthesis of embodiment 3 compound 44

[0079]

[0080] Weigh 1.24g of compound 40 and add it to 15mL of water, add 1.95g of sodium azide and 150mg of sodium iodide in sequence, react at 60°C for 96 hours, cool to room temperature, add sodium chloride to saturation, extract with dichloromethane (20mL×3 ), the organic layers were combined and dried, and concentrated to obtain 900 mg of colorless liquid compound 41, with a yield of 68.7%.

[0081] Weigh 1.25g of compound 25 and 524mg of compound 41 and dissolve it in 20mL of dichloromethane, cool to 0°C, slowly add 0.6mL of boron trifluoride ether, after the addition is completed, slowly warm up to room temperature and react overnight at room temperature, slowly to 1 mL of triethylamine was added dropwise to the reaction system, concentrated in vacuo under reduced pressure, and passed through a column (PE:EA=20:1-2:1) to obtain 1.03 g of compound 42 with a yield of 70%.

[0082] Weigh 1g of compound 42 and dissolv...

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Abstract

The invention provides a flavone derivative represented by a formula I and pharmaceutically acceptable salt, hydrate or solvate thereof. In the formula I, R1 H, is 1-4 alkyl, amino or C1-4 acyl; R2 isisopentenyl or 2-hydroxy isopentyl; R3 is H, methyl or deuterated methyl; R4 represents C1-4 alkyl, amino or C1-4 acyl or R5 represents monosaccharide residue or oligosaccharide residue; and L represents polypeptide, C1-C20 straight chain alkyl or derivative thereof, C1-C20 straight chain or branched chain acyl derivative, C1-C20 ethylene glycol or derivative thereof, wherein Y is an integer of 0to 100, b is an integer of 1 to 100, C is an integer of 1 to 10, d is an integer of 0 to 100, and e is an integer of 0 to 100. The flavone derivative has high-efficiency broad-spectrum anticancer activity.

Description

technical field [0001] The present invention relates to novel flavone derivatives and their pharmacologically acceptable salts, hydrates or solvates. The derivatives can be used as antitumor drugs. Background technique [0002] Tumor is a common disease that threatens human life. In my country, as many as one million people die from cancer every year and it is gradually increasing. It has become the first cause of death in urban population. Finding safe and effective anti-tumor drugs has always been the pursuit of the goal of the medical community. Traditional chemotherapeutic drugs have obvious therapeutic effects in clinic, but their disadvantages are low specificity and low selectivity, which lead to obvious toxic and side effects, and are prone to serious tumor multidrug resistance, which limits their clinical application. [0003] Flavonoids are a class of natural phenolic compounds that exist in plants. Their structures and physical and chemical properties are very di...

Claims

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Application Information

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IPC IPC(8): C07H19/056C07H15/26C07H1/00A61K31/7056A61K31/7028A61P35/00A23L33/00
CPCC07H19/056C07H15/26C07H1/00A61P35/00A23L33/00A23V2002/00A23V2200/308
Inventor 谢永美宋相容罗波
Owner SICHUAN FUSHENGYUAN TECH CO LTD
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