Acetyl salicyl puerarin derivatives and preparation method and use thereof

A technology of acetylsalicylic acid and acetylsalicylic acid chloride is applied in the field of medicine to achieve the effects of improving cell membrane permeability, improving oral bioavailability and reducing irritation

Active Publication Date: 2007-05-09
REYOUNG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although a series of derivatization transformations have been carried out on puerarin in the prior art, there is no report on the structural modification of puerarin with aspirin to prepare acetylsalicyloyl puerarin and its derivatives.

Method used

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  • Acetyl salicyl puerarin derivatives and preparation method and use thereof
  • Acetyl salicyl puerarin derivatives and preparation method and use thereof
  • Acetyl salicyl puerarin derivatives and preparation method and use thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0044] Mix 9.0g (about 0.05mol) of aspirin with 7ml (about 0.084mol) of thionyl chloride, add 4 drops of pyridine, slowly heat up the oil bath to 75°C within 50min, react at constant temperature for 2h, and evaporate the liquid under reduced pressure , add 6ml of anhydrous tetrahydrofuran, and keep airtight until use. Dissolve 4.2g of puerarin (about 0.01mol) in an appropriate amount of anhydrous tetrahydrofuran, add 5g of anhydrous sodium carbonate, and stir at room temperature for 10 minutes. 5.5 g (about 0.026 mol) of acetylsalicyloyl chloride was slowly added dropwise under stirring in an ice bath, and reacted at room temperature for 1 h, then refluxed for 2 h, filtered, and evaporated to remove the solvent under reduced pressure. The solid was subjected to conventional silica gel column chromatography, chloroform-methanol system gradient elution, silica gel thin layer chromatography (CHCl 3 : MeOH=8:2, 1% FeCl 3 -K 3 [Fe(CN) 6 ] (1:1) solution color development) detec...

Embodiment 2

[0048] Mix 9.0g (about 0.05mol) of aspirin with 5ml of thionyl chloride, add 4 drops of pyridine, slowly heat up the oil bath to 60°C within 50min, react at constant temperature for 2h, evaporate the liquid under reduced pressure, add 6ml of anhydrous Tetrahydrofuran, sealed and stored for later use. Dissolve 10.0 g of puerarin (about 0.025 mol) in an appropriate amount of anhydrous tetrahydrofuran, add 5 g of anhydrous sodium carbonate, and stir at room temperature for 10 min. Slowly add 5.5 g (about 0.026 mol) of acetylsalicyloyl chloride dropwise under ice-bath stirring condition, react at room temperature for 2 hours, reflux for 2 hours, filter and evaporate the solvent under reduced pressure. The solid was subjected to conventional silica gel column chromatography, chloroform-methanol system gradient elution, silica gel thin layer chromatography (CHCl 3 : MeOH=8:2, 1% FeCl 3 -K 3 [Fe(CN) 6 ] (1:1) solution color development) detects, collects and merges R f =0.65-0.8...

Embodiment 3

[0052] Mix 9g (about 0.05mol) of aspirin with 8ml of thionyl chloride, add 4 drops of pyridine, slowly heat up the oil bath to 80°C within 50min, react at constant temperature for 2h, evaporate the liquid under reduced pressure, and add 6ml of anhydrous tetrahydrofuran , sealed and stored for later use. Dissolve 6.2g of puerarin (about 0.015mol) in an appropriate amount of anhydrous tetrahydrofuran, add 5g of anhydrous sodium carbonate, and stir at room temperature for 10 minutes. 5.5 g (about 0.026 mol) of acetylsalicyloyl chloride was slowly added dropwise under stirring in an ice bath, and reacted at room temperature for 1 h, then refluxed for 3 h, filtered, and evaporated to remove the solvent under reduced pressure. The solid was subjected to conventional silica gel column chromatography, chloroform-methanol system gradient elution, silica gel thin layer chromatography (CHCl 3 : MeOH=8:2, 1% FeCl 3 -K 3 [Fe(CN) 6 ] (1:1) solution color development) detects, collects a...

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Abstract

The invention relates to a process for preparing acetyl salicyl puerarin derivatives with general formula (I) and their preparation method and use in preparation of anti-platelet aggregation medicine. The compounds have excellent inhibitory action for in vitro platelet aggregation and can be used for treating cardiovascular and cerebrovascular diseases.

Description

technical field [0001] The invention belongs to the technical field of medicine, and mainly relates to a puerarin derivative and a preparation method and application thereof, in particular to an acetylsalicyloyl puerarin derivative and the preparation and application thereof. Background technique [0002] Puerarin is a natural, low-toxic and effective drug for the treatment of cardiovascular and cerebrovascular diseases. Microalbumin, prevention of diabetic nephropathy etc. However, the poor oral absorption and bioavailability of puerarin limits the application of oral dosage forms. The injection dosage form of puerarin is mainly used in clinical practice. For the convenience of application, it is necessary to improve the solubility and bioavailability of puerarin. At present, relevant literature reports mainly focus on structural modification or the use of special dosage forms. Yang Ruolin and others have carried out a series of derivatization transformations on puerarin,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/36A61K31/352A61P7/02
Inventor 娄红祥刘丽娟范培红
Owner REYOUNG PHARMA
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