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Use of composition of triazolyl derivative and 1H-tetrazolyl derivative of Artalbic acid in preparation of anti-liver fibrosis medicines

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

Inactive Publication Date: 2016-11-09
南京海澳斯生物医药科技有限公司
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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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  • Use of composition of triazolyl derivative and 1H-tetrazolyl derivative of Artalbic acid in preparation of anti-liver fibrosis medicines
  • Use of composition of triazolyl derivative and 1H-tetrazolyl derivative of Artalbic acid in preparation of anti-liver fibrosis medicines
  • Use of composition of triazolyl derivative and 1H-tetrazolyl derivative of Artalbic acid in preparation of anti-liver fibrosis medicines

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Experimental program
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Embodiment 1

[0015] The preparation of embodiment 1 compound Artalbic acid

[0016] The preparation method of compound Artalbic acid (I) refers to the literature published by Antonella Maggio et al. (Antonella Maggio et al., 2011. Artalbic acid, a sesquiterpene with an unusual skeleton from Artemisia alba (Asteraceae) from Sicily. Tetrahedron Letters, 52 (2011) 4543–4545) approach.

[0017]

Embodiment 2

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

[0019] Compound I (266 mg, 1.00 mmol) was dissolved in 10 mL of benzene, and tetrabutylammonium bromide (TBAB) (0.08 g), 1,2-dibromoethane (3.760 g, 20.00 mmol) and 6 mL of 50% sodium hydroxide solution. The mixture was stirred at 40 °C for 16 h. After 16 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 for 5 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 (272mg, 73%) .

...

Embodiment 3

[0024] Synthesis of O-(triazolyl) ethyl derivative (III) of embodiment 3 Artalbic acid

[0025] Compound II (187mg, 0.5mmol) was dissolved in 25mL of acetonitrile, anhydrous potassium carbonate (345mg, 2.5mmol), potassium iodide (84mg, 0.5mmol) and 1,2,3-triazole (2760mg, 40mmol) were added ), the mixture was heated to reflux for 3h. 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=100:1.0, v / v), and the light yellow concentrated elution band was collected to obtain compound III as a light yellow colloidal solid (124.5mg, 69% ).

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Abstract

The invention relates to the fields of organic synthesis and pharmaceutical chemistry, and discloses a composition composed of the O-(triazolyl)ethyl derivative and the O-(1H-tetrazolyl)ethyl derivative of Artalbic acid according to a mass ratio of 20:80, and a method for preparing the composition by mixing the O-(triazolyl)ethyl derivative and the O-(1H-tetrazolyl)ethyl derivative of Artalbic acid according to the mass ratio of 20:80. Pharmacologic experiments show that the composition can substantially inhibit NIH / 3T3 propagation and transforming growth factor-beta 1 induced fibroblast propagation at 20[mu] / ml, and has an anti-liver fibrosis effect. The invention also provides a use of the composition composed of the O-(triazolyl)ethyl derivative and the O-(1H-tetrazolyl)ethyl derivative of Artalbic acid according to a mass ratio of 20:80 in the preparation of the anti-liver fibrosis medicines.

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): A61K31/41A61K31/4192A61P1/16C07D249/04C07D257/04
CPCA61K31/41A61K31/4192C07D249/04C07D257/04A61K2300/00
Inventor 丁秋菊
Owner 南京海澳斯生物医药科技有限公司
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