A matrine derivative with antitumor properties

A technology of derivatives, matrine, applied in the field of derivatives, can solve the problems of low therapeutic efficiency, poor selectivity, and cannot be widely used in clinical practice, and achieves the effect of improving anti-tumor activity and expanding types

Active Publication Date: 2018-04-17
天津市医药科学研究所
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nitrogen mustard drugs have the advantages of broad anti-tumor spectrum and strong lethality to tumor cells. The target of action is DNA, but they also have disa

Method used

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  • A matrine derivative with antitumor properties
  • A matrine derivative with antitumor properties
  • A matrine derivative with antitumor properties

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0046] Example 1

[0047] Method for preparing matrine derivative represented by general formula I:

[0048] Preparation of 13-(2-hydroxy)ethoxymatrine (Compound 1)

[0049]

[0050] Add 30mL dry ethylene glycol to a dry 100mL three-necked flask, N 2 Under the protection of the atmosphere, 0.10 g of sodium wire was put in, the temperature was raised to 50°C, and the reaction was stirred. When the sodium wire disappears completely, stop heating and cool to room temperature. Dissolve 2.00g sophocarpine in 10mL ethylene glycol, slowly drop it into the above reaction flask, gradually increase the temperature to 60℃, follow the reaction progress by TLC, after 23h, add 10mL water to the reaction solution to stop the reaction, and extract three times with 15mL chloroform , Combined extracts, anhydrous Na 2 SO 4 Dry overnight, filter, and concentrate under reduced pressure to obtain a crude yellow oil. Elution was carried out with a mixture of ethyl acetate and ethanol in a volume ratio o...

Example Embodiment

[0085] Example 2

[0086] Preparation method of matrine derivatives of general formula II

[0087] Preparation of 13-(2-amino)ethoxymatrine (Compound 2)

[0088]

[0089] Add 30mL dry ethanolamine to a dry 100mL three-necked flask, N 2 Under the protection of the atmosphere, 0.10 g of sodium wire was put in, the temperature was raised to 50°C, and the reaction was stirred. When the sodium wire disappears completely, stop heating and cool to room temperature. Dissolve 2.00 g sophocarpine in 10 mL ethanolamine, slowly drop it into the above reaction flask, gradually increase the temperature to 60°C, and follow the reaction process by TLC. After 23 hours, the raw materials have reacted completely and undergo post-processing. Add 10 mL of water to the reaction solution to stop the reaction, extract three times with 15 mL of chloroform, combine the extracts, anhydrous Na 2 SO 4 Dry overnight, filter, and concentrate under reduced pressure to obtain a crude yellow oil. Elution was carri...

Example Embodiment

[0113] Example 3

[0114] Preparation method of matrine derivatives of general formula Ⅲ

[0115] Preparation of Matrine

[0116]

[0117] Add 4.96g (0.02mol) matrine, 50mL absolute ethanol, 7.5g (0.1875mol) NaOH solid to a 100mL three-necked flask, and react at 105°C. TLC detects the progress of the reaction. After 6h, the raw materials have reacted completely. , Post-processing. After the reaction liquid is cooled, it is placed in an ice bath, the reaction liquid is neutralized with dilute sulfuric acid, the sodium sulfate is removed by suction filtration, the liquid is collected, and concentrated to dryness to obtain 4.30 g of white solid, which is matrine. The yield is 80.83%, mp197~198℃ (literature value [6] : 197.7~198.5℃).

[0118] Preparation of Ethyl Matrine (Compound 3)

[0119]

[0120] Add 1.33 g (0.005 mol) of matrine and 40 mL of absolute ethanol to a 100 mL single-necked flask, add 3.0 mL of thionyl chloride dropwise at 0°C, stir for 0.5h, and reflux at 65°C for 4h. T...

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Abstract

The invention relates to a matrine derivative, and provides a matrine derivative with characteristics of high activity, low toxicity and good antitumor performance, and uses of the matrine derivative in preparation of antitumor drugs.

Description

【Technical Field】 [0001] The present invention relates to a derivative, in particular to a matrine derivative with anti-tumor properties and a therapeutically acceptable salt thereof. 【Background technique】 [0002] Matrine is widely found in the legumes Sophora flavescens, Sophora flavescens, and Sophora flavescens root. It was isolated and confirmed for the first time in 1958. It is one of the main active components of the traditional Chinese medicine Sophora flavescens. , Analgesia, sedation, protection of myocardial ischemia, reduction of myocardial damage, anti-arrhythmia, prevention of liver fibrosis and anti-hepatitis B virus and other pharmacological effects. At present, the main preparations of matrine used in clinical practice include matrine injection, matrine suppository, matrine eye drops, matrine enteric-coated tablets, matrine capsules and so on. Recent studies have shown that matrine has a broad-spectrum anti-tumor effect, and does not damage normal cells. It can...

Claims

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Application Information

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IPC IPC(8): C07D471/22C07D471/16C07F9/6561C07J63/00A61K31/4375A61K31/675A61K31/58A61P35/00
Inventor 陶遵威张娜周运琴王文彤崔晓燕张国庆
Owner 天津市医药科学研究所
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