Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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
View PDF0 Cites 10 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
melting pointaaaaaaaaaa
Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com