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Application of composition of piperazinyl and 1H-tetrazole-based derivatives of Psiguadial A in resisting liver fibrosis

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: 2017-05-31
苏州贺澳德生物医药科技有限公司
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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 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 piperazinyl and 1H-tetrazole-based derivatives of Psiguadial A in resisting liver fibrosis
  • Application of composition of piperazinyl and 1H-tetrazole-based derivatives of Psiguadial A in resisting liver fibrosis
  • Application of composition of piperazinyl and 1H-tetrazole-based derivatives of Psiguadial A in resisting liver fibrosis

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Effect test

Embodiment 1

[0014] The preparation of embodiment 1 compound Psiguadial A

[0015] The preparation method of compound Psiguadial A (I) refers to the literature published by Meng Shao et al. (Meng Shao et al., 2010.Psiguadials A and B, Two Novel Meroterpenoids with UnusualSkeletons from the Leaves of Psidium guajava.Organic Letters 12(2010)5040- 5043) method.

[0016]

Embodiment 2

[0017] The synthesis of the O-bromoethyl derivative (II) of embodiment 2 Psiguadial A

[0018] Compound I (474 ​​mg, 1.00 mmol) was dissolved in 20 mL of benzene, tetrabutylammonium bromide (TBAB) (0.16 g), 1,2-dibromoethane (7.520 g, 40.00 mmol) and 12 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=100:0.5, v / v), the brown concentrated elution band was collected and the solvent was evaporated to obtain a brown powder of Compound II (502mg, 73%) ...

Embodiment 3

[0023] The synthesis of the O-(piperazinyl) ethyl derivative (III) of embodiment 3 Psiguadial A

[0024] Compound II (344mg, 0.5mmol) was dissolved in 25mL of acetonitrile, anhydrous potassium carbonate (690mg, 5.0mmol), potassium iodide (168mg, 1.0mmol) and anhydrous piperazine (3446mg, 40mmol) were added thereto, and the mixture was heated to reflux 4h. After the reaction, 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=100:1.0, v / v), the yellow concentrated elution band was collected and the solvent was evaporated to obtain a yellow powder of compound III (254.8...

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Abstract

The invention relates to the field of organic synthesis and medicinal chemistry, and provides a composition formed by O-(piperazinyl)ethyl derivatives (III) and O-(1H-tetrazole-based)ethyl derivatives (IV) of Psiguadial A according to the mass ratio of 10:90 and a method for preparing the composition by mixing the compouds according to the mass ratio of 10:90. Pharmacological experiments show that the composition can remarkably inhibit NIH / 3T3 proliferation and transforming growth factor-beta1 induced fibroblast proliferation at 20ug / ml, and has a liver fibrosis resisting function, and therefore the invention further provides application of the composition formed by the O-(piperazinyl)ethyl derivatives (III) and the O-(1H-tetrazole-based)ethyl derivatives (IV) of Psiguadial A according to the mass ratio of 10:90 in preparing medicine for resisting liver fibrosis. The formula is shown in the description.

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): A61K31/496A61K31/41C07D313/06C07D257/04A61P11/00
CPCA61K31/496A61K31/41C07D257/04C07D313/06
Inventor 朱磊磊
Owner 苏州贺澳德生物医药科技有限公司
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