Puerarin derivatives and preparation methods thereof

A puerarin derivative and selected technology, applied in its preparation field, can solve the problems of poor water solubility and fat solubility of puerarin, small clinical application range of puerarin, limitation of biological activity and clinical application, etc., and achieve fat solubility Good, good water solubility, high product yield

Active Publication Date: 2014-04-02
SHENZHEN JYMED TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Puerarin has poor water solubility and fat solubility, so puerarin has a small range of clinical applications and is only used for injection therapy, which limits its biological activity and clinical application

Method used

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  • Puerarin derivatives and preparation methods thereof
  • Puerarin derivatives and preparation methods thereof
  • Puerarin derivatives and preparation methods thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Synthesis of Example 1 Compound A

[0029] The synthetic route and the structural formula of each compound refer to the attached figure 1 - attached figure 2 .

[0030] (1) Synthesis of compound 2

[0031] The synthetic route and the structural formula of each compound refer to the attached figure 1 .

[0032] Dissolve N,N-dimethyl-1,3-diaminopropane (3.06g, 0.03mol) in dichloromethane (150ml), cool down to -10°C, add solid triphosgene (2.97g, 0.01mol) ; Add triethylamine (3.03g, 0.03mol) dropwise under stirring, after the dropwise addition is completed, rise to room temperature and react for 3h;

[0033] After the reaction was completed, add purified water (70ml) to quench the reaction, separate the layers, extract the aqueous layer twice with dichloromethane (70ml*2), combine the organic phases, dry over anhydrous sodium sulfate, and concentrate to obtain an oily substance (4.4g, 90%), the crude product was directly used in the next reaction.

[0034] (2) Sy...

Embodiment 2

[0038] Synthesis of Example 2 Compound B

[0039] The synthetic route and the structural formula of each compound refer to the attached image 3 - attached Figure 7

[0040] (1) Synthesis of Compound 6

[0041] The synthetic route and the structural formula of each compound refer to the attached image 3 .

[0042] Dissolve N-tert-butoxycarbonyl-4-piperidone (1.99g, 0.01mol) and N-benzylpiperazine (1.96g, 0.011mol) in methanol (40ml), and quickly add cyanoborohydrogenation under stirring Sodium (1.26g, 0.02mol), react at room temperature, adjust the pH to 7 with acetic acid during the reaction;

[0043] After the reaction was completed, the solvent was evaporated by rotary evaporation, and water (40ml) and dichloromethane (60ml) were added for extraction, the aqueous layer was washed twice with dichloromethane (40ml*2), the combined organic phase was washed with saturated brine, and the organic phase was washed with anhydrous Dry over sodium sulfate and concentrate t...

Embodiment 3

[0059] Example 3 Synthesis of Compound C

[0060] The synthetic route and the structural formula of each compound refer to the attached Figure 8 .

[0061] Put puerarin (4.16g, 0.01mol) and succinic anhydride (1.98g, 0.012mol) into dichloromethane (80ml), add DMAP (100mg), heat to reflux, and react for 24h; 20ml, separated and purified by preparative column, collected fractions, concentrated to 20 mL volume, added sodium bicarbonate to adjust pH to 8, poured the aqueous solution into ethanol (200ml), precipitated white solid, filtered, and vacuum dried to obtain white solid (3.41g, 63.3%).

[0062] At room temperature, the solubility of compound C in water is about 452 mg / ml. Mix a certain amount of compound C with rat anticoagulant plasma, incubate at 37°C, and perform HPLC analysis by solid phase extraction at different time points. The half-life of compound 7 converted into puerarin in blood is determined to be 0.46±0.31h .

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Abstract

The invention belongs to the technical field of organic synthetic chemistry, and provides a plurality of puerarin derivatives and preparation methods thereof. The prepared puerarin derivatives have good water solubility or fat solubility, and can be quickly converted into puerarin in blood or in vivo, the bioavailability is high, the preparation technology is simple, a target product has a high yield, and the product safety is high.

Description

technical field [0001] The present invention relates to several kinds of puerarin derivatives, especially to the preparation method thereof. Background technique [0002] Puerarin is a flavonoid glycoside extracted from the dried root of Pueraria Lobata (Willd. ohwi) or Pueraria thomsonii Benth (Pueraria thomsonii Benth). The chemical name is 7,4'-dihydroxy-8-β-D-glucose isoflavone, and the molecular formula is C 21 h 20 o 9 , molecular weight 416.38, CAS number 82373-94-3, is one of the important active substances in kudzu root. Puerarin has the functions of improving immunity, enhancing myocardial contractility, protecting myocardial cells, lowering blood pressure, and anti-platelet aggregation. It is widely used in the treatment of clinical hypertension, coronary heart disease, acute cerebral infarction, diabetes and other diseases. [0003] Puerarin has poor water-solubility and fat-solubility, so puerarin has a small range of clinical applications and is only used ...

Claims

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Application Information

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IPC IPC(8): C07D407/04C07D405/14
CPCC07D405/14C07D407/04
Inventor 姚志勇李新宇支钦张建松邱焕杰马洪季舒遂智
Owner SHENZHEN JYMED TECH
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