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Application of composition of Schiglautone A derivatives in preparation of anti-hepatic fibrosis drugs

A liver fibrosis and composition technology, applied in the fields of organic synthesis and medicinal chemistry, can solve the problems of lack of clinical treatment methods

Inactive Publication Date: 2016-10-26
NANJING GUANGKANGXIE BIOLOGICAL MEDICAL TECH
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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 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 composition of Schiglautone A derivatives in preparation of anti-hepatic fibrosis drugs
  • Application of composition of Schiglautone A derivatives in preparation of anti-hepatic fibrosis drugs
  • Application of composition of Schiglautone A derivatives in preparation of anti-hepatic fibrosis drugs

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Experimental program
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Effect test

Embodiment 1

[0015] The preparation of embodiment 1 compound Schiglautone A

[0016] The preparation method of compound Schiglautone A (I) refers to the literature published by Fan-Yu Meng et al. of Schisandra glaucescens. Organic Letters 13 (2011) 1502–1505).

[0017]

Embodiment 2

[0018] The synthesis of the O-bromoethyl derivative (II) of embodiment 2 Schiglautone A

[0019] Compound I (502 mg, 1.00 mmol) was dissolved in 15 mL of benzene, and tetrabutylammonium bromide (TBAB) (0.08 g), 1,2-dibromoethane (7.520 g, 40.00 mmol) and 6 mL of 50% sodium hydroxide solution. The mixture was stirred at 35 °C for 8 h. After 8 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=100:1.0, v / v), the brown concentrated elution band was collected and the solvent was evaporated to obtain a brown powder of Compound II (508mg, 71%...

Embodiment 3

[0024] The synthesis of O-(1H-tetrazolyl) ethyl derivative (III) of embodiment 3 Schiglautone A

[0025] Compound II (358 mg, 0.5 mmol) was dissolved in 15 mL of acetonitrile, anhydrous potassium carbonate (345 mg, 2.5 mmol), potassium iodide (84 mg, 0.5 mmol) and 1H-tetrazolium (1401 mg, 20 mmol) were added thereto, and the mixture was heated Reflux for 5h. 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. Because of tautomerism, two substitution products, 1H-tetrazolyl and 2H-tetrazolyl, will be generated under the reaction conditions. The crude product was purified by silica gel column chromatography (mobile phase: petroleum ether / acetone...

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Abstract

The invention relates to the field of organic synthesis and medicinal chemistry and discloses and provides a composition composed of Schiglautone A O-(1H-tetrazole)ethyl and O-(benzimidazolyl)ethyl derivatives according to a mass ratio of 65:35. Pharmacological experiments show that the composition provided herein can significantly inhibit NIH / 3T3 proliferation and transforming growth factor-induced fibroblast proliferation and can resist hepatic fibrosis; therefore, the invention also provides application of a composition composed Schiglautone A O-(1H-tetrazole)ethyl and O-(benzimidazolyl)ethyl derivatives according to the mass ratio of 65:35, in the preparation of anti-hepatic fibrosis drugs.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to a composition, 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 made great progress, ...

Claims

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Application Information

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IPC IPC(8): A61K31/4184A61K31/41A61P1/16C07D257/04C07D235/06
CPCA61K31/4184A61K31/41C07D235/06C07D257/04A61K2300/00
Inventor 陆贤
Owner NANJING GUANGKANGXIE BIOLOGICAL MEDICAL TECH
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