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Application of o-(tetrahydropyrrolyl)ethyl derivatives of cleistanone cleistanone in the preparation of anti-inflammatory drugs

A technology of tetrahydropyrrolyl and ethyl derivatives, which can be used in anti-inflammatory agents, drug combinations, medical preparations containing active ingredients, etc., and can solve the problems of high toxicity and low safety.

Inactive Publication Date: 2016-03-23
柴桂凤
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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 inflammation have the problems of high toxicity and low safety. It is of great value 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-(tetrahydropyrrolyl)ethyl derivatives of cleistanone cleistanone in the preparation of anti-inflammatory drugs
  • Application of o-(tetrahydropyrrolyl)ethyl derivatives of cleistanone cleistanone in the preparation of anti-inflammatory drugs
  • Application of o-(tetrahydropyrrolyl)ethyl derivatives of cleistanone cleistanone in the preparation of anti-inflammatory drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Preparation of Example 1 Compound Cleistanone

[0022] The preparation method of the compound Cleistanone (I) refers to the literature published by VanTrinhThiThanh et al.

[0023]

Embodiment 2

[0024] Synthesis of O-bromoethyl derivatives (II) of cleistanone Cleistanone of embodiment 2

[0025] 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%).

[0026] 1HNMR (...

Embodiment 3

[0030] Example 3 Synthesis of O-(tetrahydropyrrolyl) ethyl derivatives (III) of cleistanone Cleistanone

[0031] 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 alco...

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Abstract

The invention relates to the field of organic synthesis and medicinal chemistry and particularly to an O-(pyrrolidine) ethyl derivative of Cleistanone, a preparation method for the O-(pyrrolidine) ethyl derivative of the Cleistanone and the application of the O-(pyrrolidine) ethyl derivative of the Cleistanone in preparing anti-inflammatory drugs. The invention synthesizes a novel O-(pyrrolidine) ethyl derivative of the Cleistanone and discloses the preparation method thereof. Pharmacological experiment results show that the O-(pyrrolidine) ethyl derivative of the Cleistanone has the anti-inflammatory effect and has the value of developing anti-inflammatory drugs.

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] Inflammation occurs locally but can also affect the whole body. Local clinical features are redness, heat, swelling, pain and dysfunction. Redness and heat are due to the expansion of local blood vessels and the acceleration of blood flow due to inflammation. Swelling is caused by local inflammatory hyperemia and exudation of blood flow components. The development of drugs with anti-inflammatory effects is of great significance for the verification of relief and pain relief. [0003] The existing drugs for the treatment of inflammation have the problems of high toxicity and low safety. It is of great value to find compounds or lead compounds from natural products and carry out structural modification to obtain their derivatives, ...

Claims

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Application Information

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IPC IPC(8): A61K31/58A61P29/00C07J63/00
Inventor 柴桂凤梁慧李福艳张桂英邵秀英
Owner 柴桂凤
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