Daidzein Derivative Solubility Modification

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Solution Overview

Problem

Current daidzein derivatives for treating cardiovascular diseases face challenges due to low natural yield, poor purity, and poor water solubility, leading to low bioavailability and limited therapeutic effectiveness.

Innovation Solution

A novel daidzein derivative with specific structural modifications, represented by formula (I), and its pharmaceutically acceptable salts, such as hydrochloride, are synthesized to enhance solubility and bioavailability, involving reactions with halogenated alkyl acyl halides and amines, followed by salt formation with organic or inorganic acids.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If natural extraction of daidzein is used, then the compound can be obtained, but the yield is low and purity is poor

Engineering Contradiction:

ImproveyieldVSAvoidpurity

Core Design Contradiction:

ProductivityVSManufacturing precision

Solution Approach 1:

The patent applies chemical modification by changing the molecular structure parameters of daidzein through esterification reactions at the 7-OH position with various acyl halides and acid anhydrides, creating derivatives with improved properties while maintaining the core isoflavone structure

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent creates composite molecular structures by combining daidzein core with various substituent groups (acyl, amino acid, heterocyclic groups) to produce derivative compounds that exhibit enhanced pharmacological activity and solubility properties

Inventive Principle:

Principle #40Composite materials

2Ease of operation

If natural daidzein is used, then the compound structure is simple, but water solubility is poor and bioavailability is low

Engineering Contradiction:

Improvewater solubilityVSAvoidbioavailability

Core Design Contradiction:

Ease of operationVSReliability

Solution Approach 1:

The patent modifies the polarity and hydrophilicity parameters of daidzein by introducing polar functional groups (carboxylic acid, hydroxyl, amino groups) and ionizable groups through esterification with amino acids and heterocyclic carboxylic acids, significantly improving water solubility and oral bioavailability

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent applies local structural modification at the 7-OH position of the daidzein molecule, preserving the core structure responsible for pharmacological activity while introducing solubility-enhancing groups at a specific location that does not interfere with the primary therapeutic function

Inventive Principle:

Principle #3Local quality

Data Source

PatentEP2789604B1Daidzein derivative, pharmaceutically acceptable salt and preparation method thereof, and pharmaceutical composition containing same

Publication Date: 2020.02.12 ANHUI BIOCHEM BIO PHARMA

AI summary

Disclosed is a daidzein derivative as represented by formula (I), or pharmaceutically acceptable salt thereof. Compared to the daidzein in the prior art, the daidzein derivative hydrochloride, in particular to the 7-O-N,N-diethyl-aminoacetyl daidzein hydrochloride, prepared by the daidzein derivative of the present invention, has better solubility and effect for treating cardiovascular diseases.