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A kind of puerarin derivative b and its preparation method and application

A technology of puerarin derivatives and puerarin, applied in organic chemistry methods, drug combinations, organic chemistry, etc., can solve the problems of puerarin's poor water solubility and fat solubility, low bioavailability, and allergic reactions, etc., and achieve good results Anti-platelet aggregation effect, simple synthesis method, good water solubility effect

Active Publication Date: 2020-07-28
福州热方健康科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Since puerarin itself has poor water solubility and fat solubility, oral absorption is incomplete and bioavailability is low
Clinically, injections are mainly used, but in recent years, many adverse reactions have been found in injections, such as allergic reactions, shock, and hemolytic reactions.

Method used

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  • A kind of puerarin derivative b and its preparation method and application
  • A kind of puerarin derivative b and its preparation method and application
  • A kind of puerarin derivative b and its preparation method and application

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preparation example Construction

[0020] The preparation method of described puerarin derivative B, it comprises the following steps:

[0021] (1) Synthesis of compound A: react puerarin with chloroacetyl chloride to obtain compound A, wherein the structural formula of compound A is:

[0022]

[0023] (2) Synthesis of the target compound puerarin derivative B: react the compound A obtained in step (1) with a tertiary amine to obtain the described puerarin derivative B; wherein, the tertiary amine is triethylamine, N- One of methyl dioctylamine and N-methyl didecylamine.

[0024] Wherein, the specific operation method of the step (1) is: dissolve puerarin in the organic solvent A, add an organic base, control the temperature of the system at 0-5 ° C, slowly add the organic solvent A of chloroacetyl chloride dropwise, drop In the process of adding chloroacetyl chloride, the temperature of the control system is no more than 5°C; after the addition of chloroacetyl chloride is completed, the temperature of the ...

Embodiment 1

[0033] Synthesis of Compound A: Dissolve 4.16g (0.01mol) of puerarin in chloroform, add 1.19g of pyridine (0.015mol), control the temperature of the system at 0°C, and slowly add dropwise a chloroform solution of 1.36g of chloroacetyl chloride (0.012mol) , during the process of dropping chloroacetyl chloride, control the temperature of the system not to exceed 5°C. After the dropwise addition of chloroacetyl chloride is completed, slowly raise the temperature of the system to 28°C, and react at 28°C for 22 hours. During the reaction, use TLC followed the reaction process, and the raw material point basically disappeared after 22 hours of reaction. Afterwards, the reaction solution was concentrated to obtain a concentrate, which was purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate=10:1) to obtain 3.57 g of compound A with a yield of 72.4%.

[0034] NMR analysis: 1 H-NMR(400MHz,DMSO-d6):8.42(1H,s),7.99(1H,d),7.43(1H,d),7.35(2H,m),6.99(2H,m),5....

Embodiment 2

[0036] Synthesis of Compound A: Dissolve 4.16g (0.01mol) of puerarin in chloroform, add 0.791g of pyridine (0.01mol), control the temperature of the system at 2°C, and slowly add dropwise a chloroform solution of 1.13g of chloroacetyl chloride (0.01mol) , during the process of dropping chloroacetyl chloride, the temperature of the system is controlled not to exceed 5°C. After the dropwise addition of chloroacetyl chloride is completed, the temperature of the system is slowly raised to 25°C, and the reaction is carried out at 25°C for 24 hours. During the reaction, use TLC followed the reaction process, and the raw material point basically disappeared after 24 hours of reaction. Afterwards, the reaction solution was concentrated to obtain a concentrate, which was purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate=10:1) to obtain 3.32 g of compound A with a yield of 67.4%.

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Abstract

The invention relates to a puerarin derivative B as well as a preparation method and application thereof. The preparation method of the puerarin derivative B comprises the following steps: firstly, enabling puerarin to be in reaction with chloroacetyl chloride to obtain a compound A; secondly, enabling the compound A to be in reaction with a series of tertiary amines to obtain the puerarin derivative B. The puerarin derivative B disclosed by the invention has good water solubility and the effect of resisting platelet aggregation and can be used for preparing drugs for resisting the platelet aggregation.

Description

technical field [0001] The invention relates to a puerarin derivative B and its preparation method and application. Background technique [0002] Puerarin belongs to isoflavone compounds, which have antipyretic, sedative and protective effects on acute myocardial hemorrhage caused by pituitrin. It is clinically used for coronary heart disease, angina pectoris, hypertension, etc. [0003] Since puerarin itself has poor water solubility and fat solubility, oral absorption is incomplete and bioavailability is low. Clinically, injections are mainly used, but in recent years, it has been found that there are many adverse reactions in injections, such as allergic reactions, shock, and hemolytic reactions. Therefore, it is of great significance to modify the structure of puerarin to solve the research on its solubility and bioavailability. Contents of the invention [0004] The object of the present invention is to provide a puerarin derivative B with good water solubility and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D407/04A61P7/02
CPCA61P7/02C07B2200/07C07D407/04
Inventor 王热华
Owner 福州热方健康科技有限公司
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