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Application of composition of tetrahydropyrrolyl and morpholinyl derivatives of Virosaine A in anti-liver 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: 2016-08-03
ZHENJIANG MAKERAO BIOPHARM TECH CO LTD
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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 composition of tetrahydropyrrolyl and morpholinyl derivatives of Virosaine A in anti-liver fibrosis drugs
  • Application of composition of tetrahydropyrrolyl and morpholinyl derivatives of Virosaine A in anti-liver fibrosis drugs
  • Application of composition of tetrahydropyrrolyl and morpholinyl derivatives of Virosaine A in anti-liver fibrosis drugs

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Experimental program
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Effect test

Embodiment 1

[0015] The preparation of embodiment 1 compound VirosaineA

[0016] The preparation method of compound VirosaineA (I) refers to the method published by Bing-XinZhao et al. (Bing-XinZhao et al., 2012. VirosainesAandB, TwoNewBirdcage-ShapedSecurinegaAlkaloidswithanUnprecedentedSkeletonfromFlueggeavirosa.OrganicLetters14(2012)3096-3099).

[0017]

Embodiment 2V

[0018] Synthesis of O-bromoethyl derivative (II) of embodiment 2 VirosaineA

[0019] Compound I (235 mg, 1.00 mmol) was dissolved in 20 mL of benzene, tetrabutylammonium bromide (TBAB) (0.08 g), 1,2-dibromoethane (3.760 g, 20.00 mmol) and 5 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 (261mg, 78%) .

[0020] ...

Embodiment 3V

[0024] Synthesis of O-(tetrahydropyrrolyl) ethyl derivative (III) of embodiment 3 VirosaineA

[0025] Compound II (171 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 pyrrolidine (1420 mg, 20 mmol) were added thereto, and the mixture was heated to reflux for 1 h. After the reaction, the reaction solution was poured into ice water, extracted twice 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=100:1.5, v / v), and the light yellow concentrated elution band was collected to obtain the O-(tetrahydropyrrolyl)ethyl derivative of VirosaineA (III) P...

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Abstract

The invention relates to the field of organic synthesis and medicinal chemistry and discloses a composition consisting of tetrahydropyrrolyl derivatives and morpholinyl derivatives of Virosaine A in a mass ratio of 20:80 and a method for mixing the compounds in a mass ratio of 20:80 to prepare the composition. Pharmacological experiments indicate that the composition provided by the invention in a concentration of 20mu g / ml can remarkably inhibit the NIH / 3T3 proliferation and the fibroblast proliferation induced by transforming growth factor-beta1, and realizes an anti-liver fibrosis effect; and therefore, the invention also provides an application of the composition consisting of tetrahydropyrrolyl derivatives and morpholinyl derivatives of Virosaine A in a mass ratio of 20:80 in preparing anti-liver 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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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/5377A61K31/439A61P1/16
CPCA61K31/439A61K31/5377A61K2300/00
Inventor 蒋登旭
Owner ZHENJIANG MAKERAO BIOPHARM TECH CO LTD
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