Application of piperazinyl and dihydroxy ethylamino derivative composition of Atropurpuran to prevention and treatment of pancreatic fibrosis

A technology of pancreatic fibrosis and composition, which is applied in the fields of organic synthesis and medicinal chemistry, and can solve the problems of high toxicity and low safety

Inactive Publication Date: 2017-06-13
NANJING FUHAIAOSAI PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The existing drugs for the treatment of pancreatic fibrosis have the problems of high toxicity and low safety. It is most important to find compounds or lead co

Method used

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  • Application of piperazinyl and dihydroxy ethylamino derivative composition of Atropurpuran to prevention and treatment of pancreatic fibrosis
  • Application of piperazinyl and dihydroxy ethylamino derivative composition of Atropurpuran to prevention and treatment of pancreatic fibrosis
  • Application of piperazinyl and dihydroxy ethylamino derivative composition of Atropurpuran to prevention and treatment of pancreatic fibrosis

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Experimental program
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Embodiment 1

[0010] The preparation of embodiment 1 compound Atropurpuran

[0011] The preparation method of compound Atropurpuran (I) refers to the literature published by Pei Tang et al. (Pei Tang et al., 2009.Atropurpuran, a novel diterpene with an unprecedented pentacycliccage skeleton, from Aconitum hemsleyanum var.atropurpureum.Tetrahedron Letters50(2009)460-462 )Methods.

[0012]

Embodiment 2

[0013] The synthesis of the O-bromoethyl derivative (II) of embodiment 2 Atropurpuran

[0014] Compound I (312 mg, 1.00 mmol) was dissolved in 10 mL of benzene, 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 35 °C for 6 h. After 6h, 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 yellow powder of Compound II (309mg, 74%) .

[0...

Embodiment 3

[0019] The synthesis of O-(piperazinyl) ethyl derivative (III) of embodiment 3 Atropurpuran

[0020] Compound II (209mg, 0.5mmol) was dissolved in 16mL of acetonitrile, anhydrous potassium carbonate (345mg, 2.5mmol), potassium iodide (84mg, 0.5mmol) and anhydrous piperazine (6892mg, 80mmol) were added thereto, and the mixture was heated to reflux 2h. 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=100:0.7, v / v), and the concentrated brown elution band was collected and concentrated to give compound III as a brown solid (163 mg, 77%).

[0021] 1 H NM...

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Abstract

The invention discloses application of a piperazinyl and dihydroxy ethylamino derivative composition of Atropurpuran to prevention and treatment of pancreatic fibrosis, namely, application of a composition of an O-(piperazine)ethyl derivative and an O-(ethylamino)ethyl derivative of the Atropurpuran to a medicament for treating or preventing the pancreatic fibrosis. The invention relates to the fields of organic synthesis and pharmaceutical chemistry, in particular to a composition of Atropurpuran derivatives, a preparation method of the composition and application of the composition to preparation of a medicament for preventing or treating the pancreatic fibrosis. The invention discloses a composition of Atropurpuran derivatives and a preparation method thereof. As proved by a pharmacology experiment, the composition of the Atropurpuran derivatives has the effect of preventing or treating the pancreatic fibrosis, and has a value of developing the medicament of preventing or treating the pancreatic fibrosis.

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] Pancreatic fibrosis is a common feature of chronic pancreatitis caused by various reasons, and it is also the accompanying histopathological feature, manifested as a large number of fibroblast proliferation and extracellular matrix rich in connective tissue. It is the result of pancreatic damage and repair due to various reasons. Recently, pancreatic stellate cells and various cytokines have been found to be related to pancreatic fibrosis. The incidence of pancreatic fibrosis is increasing. There is an urgent need to develop effective and low-toxic anti-pancreatic fibrosis drugs. . [0003] The existing drugs for the treatment of pancreatic fibrosis have the problems of high toxicity and low safety. It is most important to find compounds or lead compounds from n...

Claims

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Application Information

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IPC IPC(8): A61K31/495A61K31/133C07D295/088C07C217/12A61P1/18
CPCA61K31/495A61K31/133C07C217/12C07D295/088
Inventor 王卓婷
Owner NANJING FUHAIAOSAI PHARMA CO LTD
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