Application of o-(piperidinyl)ethyl derivatives of cleistanone cleistanone in the preparation of anti-hepatic fibrosis drugs

A technology of cleusenone and liver fibrosis, applied in the direction of drug combination, medical preparations containing active ingredients, digestive system, etc., can solve the problems of lack of clinical treatment methods, and achieve good anti-hepatic fibrosis effect

Active Publication Date: 2016-12-28
徐州乐源牧业有限公司
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  • Abstract
  • Description
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  • Application Information

AI Technical Summary

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 ideal clinical treatment methods are still lacking (Liu Ping. Strengthen the research on the mechanism of anti-hepatic fibrosis. Chinese liver disease Magazine, 2005, 8(13): 561)

Method used

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  • Application of o-(piperidinyl)ethyl derivatives of cleistanone cleistanone in the preparation of anti-hepatic fibrosis drugs
  • Application of o-(piperidinyl)ethyl derivatives of cleistanone cleistanone in the preparation of anti-hepatic fibrosis drugs
  • Application of o-(piperidinyl)ethyl derivatives of cleistanone cleistanone in the preparation of anti-hepatic fibrosis drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1 Preparation of Compound Cleistanone

[0023] The preparation method of 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. 4111, August2011) approach.

[0024]

Embodiment 2

[0025] Example 2 Synthesis of O-Bromoethyl Derivatives (II) of Cleistanone

[0026] Compound I (440 mg, 1.00 mmol) was dissolved in 10 mL of benzene, and tetrabutylammonium bromide (TBAB) (0.04 g), 1,2-dibromoethane (3.760 g, 20.00 mmol) and 6 mL of 50% sodium hydroxide solution. The mixture was stirred at 25 °C for 24 h. After 24 hours, the reaction solution was poured into ice water, extracted twice with dichloromethane immediately, and the organic phase solutions were combined. Then the organic phase solution was washed with water and saturated brine three times successively, then dried with anhydrous sodium sulfate, and finally 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, v / v), and the yellow concentrated elution band was collected to obtain compound II as a yellow solid (344 mg, 63%).

[0027] 1H NMR (500MHz, DMSO-d 6...

Embodiment 3

[0031] Example 3 Synthesis of O-(piperidinyl)ethyl derivative (III) of cleistanone Cleistanone

[0032] Compound II (273 mg, 0.5 mmol) was dissolved in 20 mL of acetonitrile, anhydrous potassium carbonate (345 mg, 2.5 mmol), potassium iodide (84 mg, 0.5 mmol) and piperidine (852 mg, 10 mmol) were added thereto, and the mixture was heated to reflux for 16 h. After the reaction, the reaction solution was poured into 20 mL of ice water, extracted three times with an equal amount of dichloromethane, and the organic phases were combined. The combined organic phases were successively washed with water and saturated brine, 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=100:0.5, v / v), and the yellow concentrated elution band was collected to obtain the yellow color of the O-(piperidinyl)ethyl derivative...

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PUM

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Abstract

The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to O-(piperidinyl)ethyl derivatives of cleistanone, a preparation method and an application in the preparation of anti-hepatic fibrosis drugs. The invention synthesizes a new O-(piperidinyl) ethyl derivative of Cleistanone, and discloses its preparation method. Pharmacological experiments show that the O-(piperidinyl)ethyl derivative of Cleistanone of the present invention has an anti-hepatic fibrosis effect, and has the value of developing anti-hepatic fibrosis drugs.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to O-(piperidinyl)ethyl derivatives of cleistanone, a preparation method and uses thereof. Background technique [0002] Liver fibrosis is a dynamic process from chronic liver injury to liver cirrhosis, manifested in the synthesis and secretion of a large amount of extracellular matrix (ECM), while the degradation is absolutely or relatively insufficient, resulting in the diffuse deposition of ECM in the liver. It starts with necrosis of hepatocytes (HC), followed by inflammatory response, release of fibrogenesis mediators, activation of hepatic stellate cells (FSC), 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 an important factor affecting prognosis. [0003] In the past 20 years, the study of liver fibrosis h...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/58A61P1/16
Inventor 尚清芳姜康陈秀杰沙洁
Owner 徐州乐源牧业有限公司
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