Daidzein derivative and preparation method thereof

A technology of daidzein and its derivatives, applied in the field of modified natural pharmaceutical compounds and their modification, to achieve the effects of improving oral bioavailability, enhancing absorption, and improving water solubility

Inactive Publication Date: 2010-03-03
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Although daidzein has been derivatized by a variety of methods, and its water solubility can be improved to a certain extent, there are still problems in each of them, and further research and improvement are needed.

Method used

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  • Daidzein derivative and preparation method thereof
  • Daidzein derivative and preparation method thereof
  • Daidzein derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] 1. Example 1: Daidzein-7,4'-dioxo-diethylamino-acetate hydrochloride

[0035] The synthetic route is as follows:

[0036]

[0037] The specific operation is as follows:

[0038] (1) Preparation of 7,4′-chloroacetyldaidzein: Take a 500ml dry anhydrous round-bottomed three-neck flask, add 3g daidzein, 150ml ethyl acetate, and 10ml triethylamine, and set up a normal pressure dripping device. The mixture of 10ml of chloroacetyl chloride and 20ml of ethyl acetate was added dropwise in the ice-water bath to 0-3°C, and the dropping time was controlled within 40min. The reaction progress was monitored by TLC, and the reaction was carried out in the ice-water bath for 1.5 hours. Remove the water bath, continue to react at room temperature for 2 hours, filter with suction, and wash the obtained solid with water until neutral. The obtained solid was separated by a silica gel column, and the eluent was ethyl acetate:petroleum ether=1:1, and white powdery solid intermediate I' ...

Embodiment 2

[0040] 2. Example 2: Daidzein-4'-oxygen-diethylamino-acetate hydrochloride

[0041] The synthetic route is as follows:

[0042]

[0043] The specific operation is as follows:

[0044] (1) Preparation of 4′-chloroacetyl daidzein: Take a 500ml dry anhydrous round-bottomed three-neck flask, add 3g daidzein, 150ml ethyl acetate, and 5ml triethylamine, and set up a normal pressure dripping device. The mixture of 5ml of chloroacetyl chloride and 10ml of ethyl acetate was added dropwise in the ice-water bath to 0-3°C, and the dropping time was controlled within 40 minutes. The reaction progress was monitored by TLC, and the reaction was carried out in the ice-water bath for 1.5 hours. Remove the water bath, continue to react at room temperature for 2 hours, filter with suction, and wash the obtained solid with water until neutral. The obtained solid was separated by a silica gel column, and the eluent was ethyl acetate:petroleum ether=1:1, and intermediate I was obtained as a wh...

Embodiment 3

[0051] 3. Example 3: Daidzein 7,4'-oxygen-aminoguanidine-acetate

[0052] The synthetic route is as follows:

[0053]

[0054] The specific operation is as follows:

[0055] (1) Preparation of 7,4′-chloroacetyldaidzein: Take a 500ml dry anhydrous round-bottomed three-neck flask, add 3g daidzein, 150ml ethyl acetate, and 10ml triethylamine, and set up a normal pressure dripping device. The mixture of 10ml of chloroacetyl chloride and 20ml of ethyl acetate was added dropwise in the ice-water bath to 0-3°C, and the dropping time was controlled within 40min. The reaction progress was monitored by TLC, and the reaction was carried out in the ice-water bath for 1.5 hours. Remove the water bath, continue to react at room temperature for 2 hours, filter with suction, and wash the obtained solid with water until neutral. The obtained solid was separated by a silica gel column, and the eluent was ethyl acetate:petroleum ether=1:1, and brown powdery solid intermediate I' was obtaine...

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Abstract

The invention relates to a daidzein derivative which has the following chemical formula: in the chemical formula, at least one of R1 and R2 is carbonyl containing 1 to 3 carbon atoms, R3 and R4 are selected from alkyl, amino, amino derivative, ureido, guanidyl and amino acid containing 1 to 4 N atoms. The derivative adopts the daidzein as raw material, firstly carries out acylation with acylate reagent so as to obtain a midbody, and then obtains target product by reaction of midbody with R3 and / or R4. The derivative changes the polarity of the daidzein and space structure, improves water solubility, also improves permeability function of the cellular membrane and effectively improves the oral bioavailability thereof.

Description

1. Technical field [0001] The invention relates to a modified natural drug compound and a modification method thereof, specifically a daidzein derivative and a preparation method thereof. 2. Background technology [0002] Isoflavone compound daidzein (Daidzein, 7,4′-dihydroxyisoflavone), also known as daidzein, mainly exists in leguminous plants, such as kudzu root and soybean. Daidzein is a white powder at room temperature, odorless, non-toxic, insoluble in water, and has certain solubility in alcohol and ketone solvents. [0003] The structural formula of daidzein is as follows: [0004] [0005] The results of a large number of pharmacological experiments show that daidzein has various pharmacological effects, and has preventive and therapeutic effects on various diseases, such as: [0006] (1) It can specifically inhibit the activity of protein tyrosine kinase (TPK), improve the activity of human detoxification enzymes, and effectively prevent breast cancer, uterine...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/36A61K31/352
Inventor 冯乙巳潘宗琴许华建潘攀
Owner HEFEI UNIV OF TECH
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