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Application of O-(tetrahydropyrrole) ethyl derivative of cleistanone in preparation of medicines for preventing or treating pancreatic fibrosis

A technology of tetrahydropyrrolyl and ethyl derivatives, which can be used in drug combinations, medical preparations containing active ingredients, digestive systems, etc., can solve problems such as low safety and high toxicity, and achieve good resistance to pancreatic fibrosis. Effect

Active Publication Date: 2014-11-19
JASAN BIO MEDICINE JIAXING CO LTD
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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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  • Application of O-(tetrahydropyrrole) ethyl derivative of cleistanone in preparation of medicines for preventing or treating pancreatic fibrosis
  • Application of O-(tetrahydropyrrole) ethyl derivative of cleistanone in preparation of medicines for preventing or treating pancreatic fibrosis
  • Application of O-(tetrahydropyrrole) ethyl derivative of cleistanone in preparation of medicines for preventing or treating pancreatic fibrosis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1 Preparation of 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] Example 2 Synthesis of O-Bromoethyl Derivatives (II) of Cleistanone

[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 (500MHz, DMSO-d 6...

Embodiment 3

[0026] Example 3 Synthesis of O-(tetrahydropyrrolyl) ethyl derivatives (III) of cleistanone Cleistanone

[0027] Compound II (273 mg, 0.5 mmol) was dissolved in 20 mL of acetonitrile, anhydrous potassium carbonate (345 mg, 2.5 mmol), potassium iodide (84 mg, 0.5 mmol) and pyrrolidine (1420 mg, 20 mmol) were added thereto, and the mixture was heated to reflux for 8 h. 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, v / v), and the light yellow concentrated elution band was collected to obtain the O-(tetrahydropyrrolyl)ethyl deri...

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Abstract

The invention relates to the fields of organic synthesis and medicinal chemistry and in particular relates to an O-(tetrahydropyrrole) ethyl derivatives of cleistanone, a preparation method of the O-(tetrahydropyrrole) ethyl derivative of cleistanone as well as application of the O-(tetrahydropyrrole) ethyl derivative of cleistanone in preparation of medicines for preventing or treating pancreatic fibrosis. A novel O-(tetrahydropyrrole) ethyl derivative of the cleistanone is synthesized, and the invention also discloses a preparation method of the O-(tetrahydropyrrole) ethyl derivative. The pharmacology experiment proves that the O-(tetrahydropyrrole) ethyl derivative of the cleistanone has an effect of preventing or treating the pancreatic fibrosis and has the value of developing the medicine for 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 O-(tetrahydropyrrolyl)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 com...

Claims

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Application Information

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IPC IPC(8): A61K31/58A61P1/18
Inventor 吴俊艺黄蓉吴俊华
Owner JASAN BIO MEDICINE JIAXING CO LTD
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