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Application of matrine compounds in preparing anti-hepatic fibrosis and anti-liver cancer medicaments

An anti-hepatic fibrosis and matrine technology, applied in the field of medicine, can solve the problems of poor stability, easy elimination, and affecting the application of anti-hepatic fibrosis drugs

Inactive Publication Date: 2014-07-23
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Zhang Junping’s research found that M19 has anti-hepatic fibrosis and other diseases [Zhang Junping, 13-methylamino-18-thiomatrine compound used in the preparation of anti-hepatic fibrosis or other tissue and organ fibrosis drugs, CN 102258516 A], follow-up research found that matrine derivative M-19 has good activity, but its stability is poor, and it is easy to be eliminated when heated, which affects its application in the preparation of anti-hepatic fibrosis drugs. This application is based on the previous research. Its methylaminoacylation, thus improving the stability of the target molecule

Method used

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  • Application of matrine compounds in preparing anti-hepatic fibrosis and anti-liver cancer medicaments
  • Application of matrine compounds in preparing anti-hepatic fibrosis and anti-liver cancer medicaments
  • Application of matrine compounds in preparing anti-hepatic fibrosis and anti-liver cancer medicaments

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: Preparation of 15-thiosophocarpine

[0035] 1.0 g (0.004 mol) of sophocarpine and 2.0 g (0.005 mol, purchased from Alfa Company) of sophocarpine and 2.0 g of Lawson's reagent were placed in a 50 ml reaction bottle, 20 ml of dichloromethane was added, and the reaction was heated under reflux for 12 hours. After the reaction was completed, the solvent was removed by concentration under reduced pressure, and the crude product was passed through a silica gel column with dichloromethane:methanol (25:1) as the eluent to obtain 0.96 g of the product, with a yield of 91.2%.

Embodiment 2

[0036] Embodiment 2: 13-( N -Methyl)-amino-15-thiomatrine (M19) Preparation

[0037] Put 100 mg (0.0004 mol) of 18-thiosophocarpine in a 20 ml reaction bottle, add 2 ml of methylamino alcohol solution and 1 ml of triethylamine, and stir for 12 hours. After the reaction was completed, the solvent was removed by concentration under reduced pressure, and the crude product was passed through a silica gel column with methylene chloride:methanol (20:1) as the eluent to obtain 98 mg of the product with a yield of 83.5%.

Embodiment 3

[0038] Embodiment 3: 13-( N -methyl, N Preparation of -chloroacetyl)-amino-18-thiomatrine (WM-1 in the table)

[0039]Add M-19 (2 g, 6.8 mmol) and anhydrous potassium carbonate (1 g, 7.2 mmol) into a round-bottomed flask, vacuumize and inject 40 mL of anhydrous dichloromethane under the protection of Ar balloon. After ice bathing for 10 min, slowly drop 10 mL of anhydrous dichloromethane diluted chloroacetyl chloride (0.62 mL, 7.9 mmol) into the bottle under low temperature and rapid magnetic stirring. h The reaction was completed and monitored by TLC (dichloromethane / methanol, V / V, 10:1). Filter with celite, concentrate the filtrate under reduced pressure, add methanol to solidify and wash. The solid was dissolved in dichloromethane again, and an equal volume of methanol was added, concentrated under reduced pressure until a large amount of solid precipitated, filtered with suction to obtain a relatively pure product, and dried under reduced pressure to obtain 1.1 g, wi...

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PUM

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Abstract

The invention relates to application of compounds and salt thereof, and particularly relates to application of matrine compounds and salt thereof in preparation of anti-hepatic fibrosis and anti-liver cancer medicaments. The compounds have the advantages of remarkably inhibiting the proliferation of hepatoma cell lines Hep-G2, Hun-7, MHCC-97L, SMMC-7721 and Hep-3B and proliferation activities of fibroblast BJ, human hepatic stellate cells LX-2 and hepatic stellate cells HSC-T6, and can be used for preparing medicaments for treating hepatic fibrosis and liver cancer.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to the application of a group of matrine compounds for preparing anti-hepatic fibrosis and anti-liver cancer drugs. Background technique [0002] Liver fibrosis is the common pathological basis of all chronic liver diseases. It is caused by abnormal proliferation of connective tissue in the liver caused by various pathogenic factors, leading to excessive precipitation of diffuse extracellular matrix (ECM) in the liver. Pathological process [Kotaro S et al, Biochem Biophys Res Commun , 2013, 443(3): 950-956]. If the liver fibrosis develops further, resulting in the reconstruction of liver lobule, the formation of pseudolobule and nodule, it will become substantial liver cirrhosis, which is difficult to reverse, so it is particularly important to control the occurrence and development of liver fibrosis. Studies on the mechanism of hepatic fibrosis have shown that the activation of ...

Claims

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Application Information

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IPC IPC(8): A61K31/4375C07D471/22A61P35/00A61P1/16
Inventor 吴秋业赵庆杰苏长青邹燕徐洋李任武丁浩吴茂诚卓小斌
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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