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Application of O-(1H-tetrazole) ethyl derivative of cleistanone to preparing drug for preventing or treating pancreatic fibrosis

A technology of ethyl derivatives and pancreatic fibrosis, which is applied in drug combinations, medical preparations containing active ingredients, digestive system, etc., can solve the problems of low safety and high toxicity, and achieve good anti-pancreatic fibrosis effects

Inactive Publication Date: 2015-07-01
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 compounds from natural products and carry out structural modification to obtain their derivatives, so as to obtain potential drugs with high efficiency and low toxicity.

Method used

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  • Application of O-(1H-tetrazole) ethyl derivative of cleistanone to preparing drug for preventing or treating pancreatic fibrosis
  • Application of O-(1H-tetrazole) ethyl derivative of cleistanone to preparing drug for preventing or treating pancreatic fibrosis
  • Application of O-(1H-tetrazole) ethyl derivative of cleistanone to preparing drug for preventing or treating pancreatic fibrosis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Preparation of Example 1 Compound Cleistanone

[0018] The preparation method of the compound Cleistanone (I) refers to the literature published by Van Trinh Thi Thanh et al. , pages 4108–4111, August 2011).

[0019]

Embodiment 2

[0020] Synthesis of O-bromoethyl derivatives (II) of cleistanone Cleistanone of embodiment 2

[0021] Compound I (440 mg, 1.00 mmol) was dissolved in 10 mL of benzene, and tetrabutylammonium bromide (TBAB) (0.04 g), 1,2-dibromoethane (3.760 g, 20.00 mmol) and 6 mL of 50% sodium hydroxide solution. The mixture was stirred at 25 °C for 24 h. After 24 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, v / v), and the yellow concentrated elution band was collected to obtain compound II as a yellow solid (344 mg, 63%).

[0022] 1H NMR ...

Embodiment 3

[0026] Example 3 Synthesis of O-(1H-tetrazolyl)ethyl derivatives (III) of Cleistanone

[0027] Compound II (273mg, 0.5mmol) was dissolved in 15mL of acetonitrile, anhydrous potassium carbonate (345mg, 2.5mmol), potassium iodide (84mg, 0.5mmol) and 1H-tetrazolium (1401mg, 20mmol) were added thereto, and the mixture was heated Reflux 10h. 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. 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=100:1, v / v), and...

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Abstract

The invention relates to the fields of organic synthesis and medicinal chemistry, and relates to O-(1H-tetrazole) ethyl derivative of cleistanone, a preparation method thereof and an application thereof to preparing a drug for preventing or treating pancreatic fibrosis. The invention synthesizes a novel O-(1H-tetrazole) ethyl derivative of cleistanone and discloses a preparation method of the novel O-(1H-tetrazole) ethyl derivative. According to the pharmacology experiments, the O-(1H-tetrazole) ethyl derivative of cleistanone has the effect of preventing or treating pancreatic fibrosis, and has a value of developing a drug for preventing or treating pancreatic fibrosis.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to O-(1H-tetrazolyl)ethyl derivatives of cleistanone, a preparation method and uses 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 compound...

Claims

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Application Information

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IPC IPC(8): A61K31/58A61P1/18
Inventor 吴俊华吴俊艺黄蓉
Owner NANJING UNIV
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