Application of Cleistanone O-(piperazinyl)ethyl derivative in preparation of hepatic fibrosis resisting drugs

A technology for blocking floridone and liver fibrosis, which can be applied in the directions of drug combination, medical preparations containing active ingredients, digestive system, etc., can solve the problems of lack of clinical treatment methods, etc., and achieve good anti-liver fibrosis effect.

Active Publication Date: 2015-03-25
嘉善县魏塘资产管理有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In recent years, some anti-hepatic fibrosis treatments have emerged, including chemical drugs, biological agents, traditional Chinese medicine and gene therapy, etc., but the...

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  • Application of Cleistanone O-(piperazinyl)ethyl derivative in preparation of hepatic fibrosis resisting drugs
  • Application of Cleistanone O-(piperazinyl)ethyl derivative in preparation of hepatic fibrosis resisting drugs
  • Application of Cleistanone O-(piperazinyl)ethyl derivative in preparation of hepatic fibrosis resisting drugs

Examples

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Comparison scheme
Effect test

Embodiment 1

[0021] Example 1 Preparation of the compound Cleistanone

[0022] The preparation method of the compound Cleistanone (I) refers to the literature published by Van Trinh Thi Thanh et al. (Van Trinh Thi Thanh et al., 2011.Cleistanone: A Triterpenoid from Cleistanthus indochinensis with a New Carbon Skeleton.Volume 2011, Issue 22 , pages 4108-4111, August 2011) method.

[0023]

Embodiment 2

[0024] Example 2 Synthesis of O-bromoethyl derivative (II) of Cleistanone

[0025] Compound I (440mg, 1.00mmol) was dissolved in 10mL of benzene, tetrabutylammonium bromide (TBAB) (0.04g), 1,2-dibromoethane (3.760g, 20.00mmol) and 6mL of benzene were added to the solution 50% sodium hydroxide solution. The mixture was stirred at 25 degrees Celsius for 24 h. After 24h, the reaction solution was poured into ice water, immediately extracted with dichloromethane twice, and the organic phase solutions were combined. Then the organic phase solution was washed three times with water and saturated brine in turn, and then dried over anhydrous sodium sulfate, and finally concentrated under reduced pressure to remove the solvent to obtain the crude product. The crude product was purified by silica gel column chromatography (mobile phase: petroleum ether / acetone=100:1, v / v), and the yellow concentrated elution band was collected to obtain compound II as a yellow solid (344 mg, 63%).

[0026...

Embodiment 3

[0030] Example 3 Synthesis of O-(piperazinyl) ethyl derivative (III) of Cleistanone

[0031] Compound II (273 mg, 0.5 mmol) was dissolved in 30 mL of acetonitrile, and anhydrous potassium carbonate (690 mg, 5.0 mmol), potassium iodide (168 mg, 1.0 mmol) and anhydrous piperazine (3446 mg, 40 mmol) were added thereto, and the mixture was heated to reflux 3h. After the reaction, the reaction solution was poured into ice water, extracted twice with the same amount of dichloromethane, and the organic phases were combined. The combined organic phase was washed with water and saturated brine in turn, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (mobile phase: petroleum ether / acetone=100:1.5, v / v), and light brown concentrated elution bands were collected to obtain compound III as a light brown solid (196.9 mg, 71%).

[0032] 1H NMR(500MHz,DM...

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Abstract

The invention relates to the field of organic synthesis and pharmaceutical chemistry and particularly relates to a Cleistanone O-(piperazinyl)ethyl derivative, a preparation method thereof and use thereof in the preparation of hepatic fibrosis resisting drugs. According to the invention, a novel Cleistanone O-(piperazinyl)ethyl derivative is synthesized, and a preparation method of the novel Cleistanone O-(piperazinyl)ethyl derivative is disclosed. Shown by pharmacological experiments, the Cleistanone O-(piperazinyl)ethyl derivative disclosed by the invention has a hepatic fibrosis resisting effect and has a value in the development of the hepatic fibrosis resisting drugs.

Description

Technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to the O-(piperazinyl) ethyl derivative of octodecone, a preparation method and application thereof. Background technique [0002] Liver fibrosis is a dynamic process from chronic liver injury to cirrhosis. It is manifested as a large amount of extracellular matrix (ECM) synthesis and secretion, and absolute or relatively insufficient degradation, which makes ECM diffusely deposit in the liver. It starts with hepatocyte (HC) necrosis, followed by inflammation, fibrogenesis mediator release, hepatic stellate cell (FSC) activation, and finally the synthesis and degradation of liver connective tissue components are obviously out of balance. Liver fibrosis is a common pathological process of many chronic liver diseases, and it is an important factor affecting the prognosis. [0003] In the past 20 years, great progress has been made in liver fibrosis research, confirm...

Claims

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Application Information

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IPC IPC(8): A61K31/58A61P1/16C07J63/00
CPCA61K31/58C07J63/008A61K2300/00
Inventor 皋林黄蓉吴俊艺吴俊华
Owner 嘉善县魏塘资产管理有限公司
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