Application of O-(piperazinyl) ethyl derivative of cleistanone to preparation of medicine for resisting acute gout

An ethyl derivative, a technology of cylinone, applied in the field of preparation of O-ethyl derivatives of cysanone, can solve the problems of aplastic anemia, neutropenia, etc., achieve inhibiting expression, improving cell activity, The effect of reducing apoptosis

Inactive Publication Date: 2015-01-21
广州往圣生物科技有限公司
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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 diarrhea and other gastrointestinal symptoms. Absolutely contraindicated in the case of bleeding, and the administration of phenylbutazone for as short as 3 weeks can also cause severe neutropenia or aplastic anemia

Method used

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  • Application of O-(piperazinyl) ethyl derivative of cleistanone to preparation of medicine for resisting acute gout
  • Application of O-(piperazinyl) ethyl derivative of cleistanone to preparation of medicine for resisting acute gout
  • Application of O-(piperazinyl) ethyl derivative of cleistanone to preparation of medicine for resisting acute gout

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Preparation of Example 1 Compound Cleistanone

[0025] 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).

[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] Synthesis of O-(piperazinyl) ethyl derivative (III) of cleistanone Cleistanone of embodiment 3

[0034] Compound II (273mg, 0.5mmol) was dissolved in 30mL of acetonitrile, anhydrous potassium carbonate (690mg, 5.0mmol), potassium iodide (168mg, 1.0mmol) and anhydrous piperazine (3446mg, 40mmol) were added thereto, and the mixture was heated to reflux 3h. 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=100:1.5, v / v), and the light brown concentrated elution band was collected to obtain compound III as a light brown solid (196.9 mg, 71%).

[003...

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Abstract

The invention relates to the fields of organic synthesis and pharmaceutical chemistry, in particular to O-(piperazinyl) ethyl derivative of cleistanone, and a preparation method and the application of the O-(piperazinyl) ethyl derivative to the preparation of medicine for resisting acute gout. The invention compounds new O-(piperazinyl) ethyl derivative, and discloses a preparation method thereof. Pharmacology experiments show that the O-(piperazinyl) ethyl derivative has the effect of resisting acute gout, and has the value of developing medicine for resisting acute gout.

Description

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

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/58A61P19/06C07J63/00
CPCA61K31/58C07J63/008
Inventor 江春平朱延通罗东君吴俊华
Owner 广州往圣生物科技有限公司
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