A polymerizable acid-sensitive amphiphilic compound

A technology of amphiphilic compounds and polymeric acids, applied in the preparation of organic compounds, organic chemistry, carboxylate preparation, etc., can solve the problems of poor solubility, poor solubility of nanomaterials, and limit the practical application of nanomaterials, and achieve full reaction Complete, high-yield results

Active Publication Date: 2021-12-24
THE EYE HOSPITAL OF WENZHOU MEDICAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the human body, some environments are watery environments, and some environments are oily (fat-soluble) environments; but existing nanomaterials are either poorly soluble in aqueous solutions or poorly soluble in oily solutions, so greatly Limits the practical application of nanomaterials in the field of drug carriers

Method used

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  • A polymerizable acid-sensitive amphiphilic compound
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  • A polymerizable acid-sensitive amphiphilic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Step 1: Stir and mix 0.192g (1.1mmol) 1,10-decanediol, 0.111g (1.1mmol) triethylamine and 20ml dichloromethane at 5°C at a speed of 600r / min to form the first mixed solution ;

[0049] Step 2: Mix 0.090g (1mmol) of acryloyl chloride and 20ml of dichloromethane into a constant pressure dropping funnel to completely dissolve them to form a second mixed solution;

[0050]Step 3: Pour the second mixed solution obtained in step 2 into the first mixed solution obtained in step 1, stir and mix, and react at a temperature of 25°C and a rotational speed of 1800r / min, and the reaction time is 20h; the reaction ends After filtering to remove the precipitate, dry at 35°C and 0.09Mpa for 10 minutes to obtain the crude product; the crude product was separated by silica gel column chromatography (petroleum ether: ethyl acetate = 1:1) to obtain the pure product A;

[0051] Step 4: Dissolve the obtained product A and 0.009g (0.05mmol) p-toluenesulfonic acid in 20mol methylene chloride,...

Embodiment 2

[0059] Step 1: Stir and mix 0.074g (1.2mmol) ethylene glycol, 0.141g (1.4mmol) triethylamine and 20ml methylene chloride at 5°C at a speed of 600r / min to form the first mixed solution;

[0060] Step 2: Mix 0.109g (1.2mmol) of acryloyl chloride and 20ml of dichloromethane into a constant pressure dropping funnel to completely dissolve it to form a second mixed solution;

[0061] Step 3: Pour the second mixed solution obtained in step 2 into the first mixed solution obtained in step 1, stir and mix, and react at a temperature of 20°C and a rotational speed of 1800r / min, and the reaction time is 18h; the reaction ends After filtering to remove the precipitate, dry at 35°C and 0.09Mpa for 10 minutes to obtain the crude product; the crude product was separated by silica gel column chromatography (petroleum ether: ethyl acetate = 1:1) to obtain the pure product A;

[0062] Step 4: Dissolve the obtained product A and 0.009g (0.05mmol) p-toluenesulfonic acid in 20mol methylene chlorid...

Embodiment 3

[0070] Step 1: Stir and mix 0.106g (0.9mmol) 1,6-hexanediol, 0.081g (0.8mmol) triethylamine and 20ml dichloromethane at 5°C at a speed of 600r / min to form the first mixed solution ;

[0071] Step 2: Mix 0.073g (0.8mmol) of acryloyl chloride and 20ml of dichloromethane into a constant pressure dropping funnel to completely dissolve it to form a second mixed solution;

[0072] Step 3: Pour the second mixed solution obtained in step 2 into the first mixed solution obtained in step 1, stir and mix, and react at a temperature of 30°C and a rotational speed of 1800r / min, and the reaction time is 22h; the reaction ends After filtering to remove the precipitate, dry at 35°C and 0.09Mpa for 10 minutes to obtain the crude product; the crude product was separated by silica gel column chromatography (petroleum ether: ethyl acetate = 1:1) to obtain the pure product A;

[0073] Step 4: Dissolve the obtained product A and 0.009g (0.05mmol) p-toluenesulfonic acid in 20mol methylene chloride,...

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Abstract

The invention discloses a polymerizable acid-sensitive amphiphilic compound, which is divided into two parts by using substance C, glycol and diethylene glycol monovinyl ether as raw materials, using p-toluenesulfonic acid as a catalyst, and dichloromethane as a solvent. The reaction is carried out in one step; wherein the substance C is any one of acryloyl chloride, methacryloyl chloride, and 2-ethacryloyl chloride; the dibasic alcohol is ethylene glycol, 1,3-propylene glycol, 1,4-butanediol, Any one of 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol and 1,10-decanediol Acid-sensitive amphiphilic compound, one end is a lipophilic group, the other end is a hydrophilic group, has amphiphilicity, has good solubility in aqueous solution and oily solution, and can self-assemble in water Nano-micelle; can degrade under acidic conditions; can be used as a drug carrier, especially suitable as a targeting carrier for some anti-cancer drugs; one end is a double bond, which is prone to polymerization and generates new substances, which can be used as medical materials.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a polymerizable acid-sensitive amphiphilic compound. Background technique [0002] Drug carrier refers to a system that can change the way the drug enters the human body and its distribution in the body, control the release rate of the drug and deliver the drug to the target organ; drug carrier materials play a very important role in the research of controlled release preparations; There are many types of drug carriers, and the more mature ones include microcapsules and microspheres, nanomaterials and liposomes. [0003] Among them, the use of nanomaterials as drug carriers can achieve targeted delivery and sustained release of drug delivery. Nanomaterials can penetrate many biological barriers to reach the lesion, such as delivering drugs to the brain through the blood-brain barrier. disease has the potential to be cured. In the human body, some environments are watery environ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/00C07C67/29C07C69/54A61K47/34
CPCC08G65/002C07C69/54A61K47/34
Inventor 李智慧李钟玉卢成洁
Owner THE EYE HOSPITAL OF WENZHOU MEDICAL UNIV
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