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Novel paeonol oxime compound as well as preparation method and medical application thereof

A technology of paeonol oxime and compound, which is applied in the field of new paeonol oxime compound and its preparation, can solve the problems of easy metabolism and poor water solubility, clinical application limitation, easy volatility, etc.

Pending Publication Date: 2021-04-27
何黎琴
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Paeonol has great potential in the prevention and treatment of cardiovascular diseases, but its clinical application is limited due to its volatility, easy metabolism and poor water solubility.

Method used

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  • Novel paeonol oxime compound as well as preparation method and medical application thereof
  • Novel paeonol oxime compound as well as preparation method and medical application thereof
  • Novel paeonol oxime compound as well as preparation method and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0117] Preparation of Paeonol Bromohexyl Ether (1)

[0118]Put paeonol (1.66g, 0.01mol), NaOH (2.4g, 0.06mol), 10mL DMF in a 50mL round bottom flask, and stir at room temperature for 20min. Then 1,6-dibromoethane (4.6 mL, 0.03 mol) was added, and the reaction was stirred at 25°C, and the reaction progress was tracked by TLC. After the reaction was completed, the reaction solution was slowly poured into 200 mL of ice water, and extracted with dichloromethane (DCM) (100 mL×3). The organic phase was washed with saturated NaCl solution (100mL×1), anhydrous sodium sulfate (NaCl 2 SO 4 )dry. It was filtered, concentrated, and separated by column chromatography [V (ethyl acetate): V (petroleum ether) = 1: 15] to obtain 2.59 g of a white solid with a yield of 78.7%. m.p.43.0~44.9℃.

[0119] Preparation of 2-[6-(1-morpholine)hexyloxy]paeonol(2)

[0120] Weigh paeonol bromohexyl ether (0.987g, 3mmol) into a 50mL round bottom flask, add 6mL of acetonitrile to dissolve, add dropwise...

Embodiment 2

[0124] Preparation of Paeonol Bromoamyl Ether (1)

[0125] Put paeonol (1.66g, 0.01mol), NaOH (2.4g, 0.06mol), 10mL DMF in a 50mL round bottom flask, and stir at room temperature for 20min. Then 1,5-dibromopentane (4.1 mL, 0.03 mol) was added, the reaction was stirred at 25°C, and the reaction progress was monitored by TLC. After the reaction was completed, the reaction solution was slowly poured into 200 mL of ice water, and extracted with dichloromethane (DCM) (100 mL×3). The organic phase was washed with saturated NaCl solution (100mL×1), anhydrous sodium sulfate (NaCl 2 SO 4 )dry. It was filtered, concentrated, and separated by column chromatography [V (ethyl acetate): V (petroleum ether) = 1: 15] to obtain 2.44 g of a white solid with a yield of 77.5%. m.p.38.0~39.7℃.

[0126] Preparation of 2-[5-(1-piperidine)pentyloxy]paeonol(2)

[0127] Weigh paeonol bromoamyl ether (0.630g, 2mmol) into a 50mL round bottom flask, add 6mL of acetonitrile to dissolve, add piperidin...

Embodiment 3

[0131] Preparation of Paeonol Bromobutyl Ether (1)

[0132] Put paeonol (1.66g, 0.01mol), NaOH (2.4g, 0.06mol), 10mL DMF in a 50mL round bottom flask, and stir at room temperature for 20min. Then 1,4-dibromobutane (3 mL, 0.03 mol) was added, the reaction was stirred at 25°C, and the reaction progress was tracked by TLC. After the reaction was completed, the reaction solution was slowly poured into 200 mL of ice water, and extracted with dichloromethane (DCM) (100 mL×3). The organic phase was washed with saturated NaCl solution (100mL×1), anhydrous sodium sulfate (NaCl 2 SO 4 )dry. It was filtered, concentrated, and separated by column chromatography [V (ethyl acetate): V (petroleum ether) = 1: 15] to obtain 2.35 g of a white solid with a yield of 78.1%. m.p.42.9-44.3°C.

[0133] Preparation of 2-[4-(4-methylpiperazine)butoxy]paeonol(2)

[0134] Weigh paeonol bromobutyl ether (0.602g, 2mmol) in a 50mL round bottom flask, add 6mL of acetonitrile to dissolve, add dropwise 4...

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PUM

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Abstract

The invention discloses a novel paeonol oxime compound as well as a preparation method and medical application thereof . A natural active ingredient paeonol with anti-platelet aggregation activity is used as a lead compound, 2-position phenolic hydroxyl and 1-position keto carbonyl of paeonol are used as modification sites, amino etherification is firstly performed on 2-position hydroxyl, improvement of metabolic stability and water solubility is facilitated, and then keto carbonyl oximation is performed on paeonol to improve the anti-platelet aggregation activity of paeonol. The invention particularly relates to a preparation method of a novel paeonol oxime compound and application of the novel paeonol oxime compound in pharmacy. The compound has an anti-platelet aggregation effect and can be used for preparing medicines for treating cardiovascular and cerebrovascular diseases.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry and pharmacotherapeutics, in particular to a novel paeonol oxime compound, a preparation method thereof and an application in pharmacy. The compounds have the effect of anti-platelet aggregation and can be used to prepare medicines for treating cardiovascular and cerebrovascular diseases. The invention also relates to processes for the preparation of such compounds. Background technique [0002] Thromboembolism is the main cause of cardiovascular and cerebrovascular diseases. The incidence of thromboembolic diseases is the highest among all kinds of diseases, and it has high disability and death rates. Studies have found that the occurrence of thrombotic diseases is related to many factors, such as: damage to endothelial cells of blood vessels can cause abnormalities in coagulation factors and coagulation system, and platelet adhesion and aggregation will occur, thereby generating thrombus; t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/48C07C249/08C07D295/088A61K31/5375A61K31/4453A61K31/495A61K31/15A61P7/02A61P9/00A61P9/10A61P9/06A61P25/00
CPCC07C251/48C07C249/08C07D295/088A61P7/02A61P9/00A61P9/10A61P9/06A61P25/00C07B2200/07
Inventor 何黎琴戴卫国尚飞扬何冰顾宏霞
Owner 何黎琴
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