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Application of diethylamine derivative of Cleistanine in preparation of anti-hepatic fibrosis medicines

A technology for occludone and liver fibrosis, which is applied in the directions of drug combination, medical preparations containing active ingredients, and pharmaceutical formulations, can solve problems such as lack of clinical treatment methods, and achieve good anti-liver fibrosis effect.

Active Publication Date: 2014-10-15
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • 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 diethylamine derivative of Cleistanine in preparation of anti-hepatic fibrosis medicines
  • Application of diethylamine derivative of Cleistanine in preparation of anti-hepatic fibrosis medicines
  • Application of diethylamine derivative of Cleistanine in preparation of anti-hepatic fibrosis medicines

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Example 1 Preparation of Compound Cleistanone

[0023] The preparation method of the compound Cleistanone (I) refers to the literature published by Van Trinh Thi Thanh et al. –4111, August2011).

[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-(diethylamino)ethyl derivatives (III) of cleistanone Cleistanone

[0032]Compound II (273mg, 0.5mmol) was dissolved in 20mL of acetonitrile, anhydrous potassium carbonate (345mg, 2.5mmol), potassium iodide (84mg, 0.5mmol) and diethylamine (1460mg, 20mmol) were added thereto, and the mixture was heated to reflux for 8h . After the reaction was completed, the reaction solution was poured into 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=100:1, v / v), and the light yellow concentrated elution band was collected to obtain compound III as a light yellow colloidal solid (169...

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Abstract

The invention relates to the field of organic synthesis and medicinal chemistry, in particular to a derivative of Cleistanine, a preparation method and application of Cleistanine in preparation of anti-hepatic fibrosis medicines. According to the invention, a novel Cleistanine derivative is synthesized and the invention discloses the preparation method thereof; the pharmacological experiments show that the derivative of Cleistanine has anti-hepatic fibrosis effect and value for developing anti-hepatic fibrosis medicines.

Description

technical field [0001] The present invention relates to the fields of organic synthesis and medicinal chemistry, in particular to a Cleistanone derivative, a preparation method and an application 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 has ma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/56A61P1/16C07J63/00
Inventor 皋林黄蓉吴俊艺吴俊华
Owner NANJING UNIV
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