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Sauchinone derivative and preparing method and application thereof

A technology of salicylicone and derivatives, applied in the field of medicinal chemistry research, can solve the problems of low adverse reactions and the like, and achieve the effects of low adverse reactions, high purity and low cost

Inactive Publication Date: 2013-05-01
NANJING UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Purpose of the invention: The technical problem to be solved by the present invention is to overcome the deficiencies of the prior art and use tribacudone as a raw material through selective reduction and esterification to synthesize a series with medicinal value, good solubility and high bioavailability , low adverse reactions, and safe medication of tribaurumone derivatives. Another object of the present invention is to provide a preparation method of tribaurumone derivatives and its application in the preparation of drugs for preventing and treating liver diseases such as hepatitis and cirrhosis.

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  • Sauchinone derivative and preparing method and application thereof
  • Sauchinone derivative and preparing method and application thereof
  • Sauchinone derivative and preparing method and application thereof

Examples

Experimental program
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Embodiment 1 3

[0030] Example 1 Preparation of Tribaurumone Derivatives (1)

[0031] Take 1g (2.8mmol) of tribauronone in a 100mL round bottom flask, add 20mL of tetrahydrofuran to dissolve; put 0.54g (14mmol) of NaBH 4 Slowly dissolve in 20mL methanol solution to which 20mg NaOH has been added, drop the methanol solution dropwise into the tetrahydrofuran solution of tribagudone that has been pre-cooled in an ice-water bath, react in the ice-water bath for 0.5h, remove the ice bath, and naturally The temperature was raised to room temperature, and the progress of the reaction was detected by thin-layer chromatography, and the reaction was complete after about 3 hours. The reaction solution was rotary evaporated to dryness at 40°C, and the solid was dispersed by ultrasonic dispersion with 100 mL of water, filtered, and the obtained solid was dried and then subjected to silica gel column chromatography, eluting with petroleum ether: ethyl acetate = 10:1, to obtain the tribaquidone derivative (...

Embodiment 2

[0038] Preparation of embodiment 2 derivative (2)

[0039] Add 100mg (0.28mmol) of tribagudone derivative (1) prepared according to the method in the example to a 50mL round-bottomed flask, add 3mL of pyridine to dissolve, then add 0.26mL (2.8mmol) of acetic anhydride, and add 1mg 4 dropwise - 0.5mL pyridine solution of dimethylaminopyridine (DMAP) was catalyzed, reacted at room temperature for 24h, and detected the end point by TLC. After the reaction, wash with 50 mL of distilled water, add 30 mL of ethyl acetate to extract twice, combine the organic phase, wash the organic phase with 30 mL of 1mol / L hydrochloric acid to remove pyridine and DMAP, and wash with 30 mL of saturated NaHCO 3 The solution neutralized the excess acid, and then washed with saturated NaCl until the solution was neutral, and the organic phase was washed with anhydrous NaCl 2 SO 4 Dry, filter, and concentrate to dryness under reduced pressure. Add a small amount of ethanol for recrystallization to o...

Embodiment 3

[0044] Example 3 Pharmacodynamic evaluation of mouse liver injury caused by carbon tetrachloride

[0045] A. Take 50 mice and randomly divide them into 6 groups, namely normal group, model group, and tribaquidone 10, 20, 50 mg / kg dosage groups, with 10 mice in each group. After three days of adaptive feeding, except the normal group and the model group were given the same volume of 0.5% sodium carboxymethyl cellulose solution for intragastric administration, the other groups were given different doses of tribaquidone by intragastric administration, once a day, continuously 7 days. One hour after the last administration, mice in other groups were intraperitoneally injected with 0.1% CCl except for the normal group given an equal volume of peanut oil. 4 Peanut oil 10mL / kg, then fasting without food and water, after an interval of 16 hours, blood was taken from the orbital vein, the blood sample was placed in a water bath at 37°C for 30 minutes, then centrifuged at 3500r / min for 1...

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Abstract

The invention relates to the field of chemical research of drugs, and particularly discloses a sauchinone derivative and a preparing method and an application thereof. A ketonic group is selectively reduced into a free hydroxyl group, or the hydroxyl group is esterified, so the biological solubility is improved, the biological utilization degree after the sauchinone derivative is taken by people is improved, the pharmacological activity is improved, the adverse reaction is low, the safety in taking of the sauchinone derivative is realized, the sauchinone derivative can be prepared into drug preparations of multiple types, and the convenience in clinical medication is realized. The preparing method provided by the invention has the advantages that the operability is high, the production efficiency is high, the cost is low, and the purity is high. After being proved by experiment results, the sauchinone derivative provided by the invention has the advantages that the solubility is good, the biological utilization degree is higher, the hepatic injury-resistance efficiency is better, and the sauchinone derivative can be developed into new drugs for preventing and controlling hepatic diseases.

Description

technical field [0001] The invention relates to the field of medicinal chemistry research, in particular to tribaurumone derivatives, their preparation methods and their application in liver-protecting drugs. Background technique [0002] With the development of science and technology and economy in the world, the acceleration of people's life rhythm and the continuous improvement of living standards, the incidence of liver diseases such as fatty liver, alcoholic liver, and liver cancer is also increasing. my country is a big country with liver disease. At present, there are 120 million liver disease patients, and more than 20% of them have transformed into liver cirrhosis or liver cancer. For healthy people, many unhealthy living habits in modern society are eroding people's livers. Alcoholic liver and fatty liver are becoming younger and popular, which seriously affect the physical fitness of my country's hard-core people. Therefore, liver-protecting drugs have become new ...

Claims

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Application Information

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IPC IPC(8): C07D493/20A61K31/36A61P1/16
Inventor 徐春蕾李祥吴玉兰薛平
Owner NANJING UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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