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Applications of cleistanone O-(benzimidazolyl) ethyl derivative in preparation of drugs for preventing or treating pancreatic fibrosis

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

Inactive Publication Date: 2015-08-12
NANJING GUANGKANGXIE BIOLOGICAL MEDICAL TECH
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  • 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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  • Applications of cleistanone O-(benzimidazolyl) ethyl derivative in preparation of drugs for preventing or treating pancreatic fibrosis
  • Applications of cleistanone O-(benzimidazolyl) ethyl derivative in preparation of drugs for preventing or treating pancreatic fibrosis
  • Applications of cleistanone O-(benzimidazolyl) ethyl derivative in preparation of drugs 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-(benzimidazolyl) ethyl derivatives (III) of cleistanone 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 benzimidazole (1180mg, 10mmol) were added thereto, and the mixture was heated to reflux for 5h . 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=100:1.5, v / v), and the concentrated brown elution band was collected and concentrated to give compound III as a brown solid (105.2...

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Abstract

The invention relates to the fields of organic synthesis and pharmaceutical chemistry, and specifically relates to a cleistanone O-(benzimidazolyl) ethyl derivative, a preparation method thereof, and applications of the cleistanone O-(benzimidazolyl) ethyl derivative in the preparation of drugs for preventing or treating pancreatic fibrosis. A novel cleistanone O-(benzimidazolyl) ethyl derivative is synthesized, and a preparation method thereof is disclosed. Pharmacology experiment results show that the provided cleistanone O-(benzimidazolyl) ethyl derivative has an effect on preventing or treating pancreatic fibrosis, and thus the cleistanone O-(benzimidazolyl) ethyl derivative is advantageously used to produce drugs 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-(benzimidazolyl)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 compoun...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/58A61P1/18C07J63/00
Inventor 吴俊艺黄蓉
Owner NANJING GUANGKANGXIE BIOLOGICAL MEDICAL TECH
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