Application of cleistanone O-(benzimidazolyl) ethyl derivative in preparation of drugs for treating acute gout

A technology for cleistanone and acute gout, which is applied in the field of preparation of cleistanone derivatives and can solve the problems of granulocytopenia, aplastic anemia and the like, and achieve the effects of inhibiting expression, improving cell activity and reducing cell apoptosis.

Inactive Publication Date: 2015-08-12
NANJING GUANGKANGXIE BIOLOGICAL MEDICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although they have fast anti-inflammatory and analgesic effects, their toxic and side effects are also quite obvious. For example, the effective dose of colchicine is similar to the dose that produces diarrhe

Method used

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  • Application of cleistanone O-(benzimidazolyl) ethyl derivative in preparation of drugs for treating acute gout
  • Application of cleistanone O-(benzimidazolyl) ethyl derivative in preparation of drugs for treating acute gout
  • Application of cleistanone O-(benzimidazolyl) ethyl derivative in preparation of drugs for treating acute gout

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Preparation of Example 1 Compound Cleistanone

[0025] The preparation method of compound Cleistanone (I) refers to the literature published by Van Trinh Thi Thanh et al. (Van Trinh Thi Thanh et al., 2011.Cleistanone: A Triterpenoid from Cleistanthus indochinensis with a New Carbon Skeleton. , pages 4108–4111, August 2011).

[0026]

Embodiment 2

[0027] Synthesis of O-bromoethyl derivatives (II) of cleistanone Cleistanone of embodiment 2

[0028] 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%).

[0029] 1H NMR ...

Embodiment 3

[0033] Example 3 Synthesis of O-(benzimidazolyl) ethyl derivatives (III) of cleistanone Cleistanone

[0034] 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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PUM

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Abstract

The invention relates to the fields of organic synthesis and pharmaceutical chemistry, and specifically relates to a cleistanone derivative, a preparation method thereof, and an application of the cleistanone derivative in the preparation of drugs for treating acute gout. A novel cleistanone derivative is synthesized, and a preparation method thereof is disclosed. The pharmacological experiments show that the cleistanone derivative has an effect on resisting acute gout and can be used to develop drugs for treating acute gout.

Description

technical field [0001] The present invention relates to the fields of organic synthesis and medicinal chemistry, in particular to a Cleistanone derivative, a preparation method and an application thereof. Background technique [0002] Gout, also known as gouty arthritis, is a disease caused by the disorder of purine metabolism in the body. It is manifested by excessive uric acid in the blood, and it is easy to cause urate (MSU) to crystallize in joints and other tissues. The acute attack of gout is due to the local neutrophil infiltration and inflammatory response caused by MSU deposited in the joints. [0003] Western medicine selects three kinds of medicines for use in the acute attack stage of gout: colchicine, non-steroidal anti-inflammatory drugs and corticosteroids. The mechanism of action of colchicine is to bind to the tubulin of neutrophils, thereby hindering the activity of granulocytes and inhibiting granulocyte infiltration. Non-steroidal anti-inflammatory drug...

Claims

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Application Information

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IPC IPC(8): A61K31/58A61P19/06A61P29/00C07J63/00
Inventor 江春平朱延通罗东君
Owner NANJING GUANGKANGXIE BIOLOGICAL MEDICAL TECH
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