Aspirin derivative as well as preparation method, medicine and application thereof

A technology of aspirin and derivatives, which is applied in the field of preparation of aspirin derivatives and can solve the problems of poor curative effect of aspirin

Active Publication Date: 2020-06-30
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The aspirin prodrug provided by the present invention has the ability to sensitively release aspirin or salicylic acid under the stimulation of active oxygen or ultraviolet light, and can be enriched in tumor or inflammatory sites to improve the metabolic pathway of aspirin in vivo, thereby effectively solving the problem of aspirin's insufficient curative effect good question

Method used

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  • Aspirin derivative as well as preparation method, medicine and application thereof
  • Aspirin derivative as well as preparation method, medicine and application thereof
  • Aspirin derivative as well as preparation method, medicine and application thereof

Examples

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preparation example Construction

[0142] The invention provides a kind of preparation method of aspirin derivatives, comprising the following steps:

[0143] 1) After mixing and reacting the compound having the structure of formula (IV), the compound having the structure of (V), aspirin having the structure of (VI) and the first organic solvent, an aspirin derivative having the structure of formula (I) is obtained;

[0144]

[0145] in,

[0146] R 1 selected from borate pinacol ester groups or hydrogen atoms;

[0147] R 2 selected from a hydrogen atom or a nitro group;

[0148] R 3 A straight-chain alkyl group selected from C1-C5;

[0149] R 4 selected from ethynyl or vinyl.

[0150] The present invention has the group and specific selection of the aspirin derivatives with the structure of formula (I) in the above preparation method, and the corresponding preferred principle, which is the same as the group and The specific selections and corresponding optimization principles can preferably be corres...

Embodiment 1

[0252]

[0253] Dissolve 2.0 g (11.2 mmol) of aspirin, 2.4 g (11.2 mmol) of 4-formylphenylboronic acid pinacol ester and 1.2 g (12.9 mmol) of 5-isocyano-1-pentyne in 1 mL of chloroform, Under the condition that the temperature was 35°C, the reaction was stirred for 72 hours. After the reaction is over, add 50 mL of dichloromethane to the reaction system, wash with saturated brine and deionized water successively, dry the organic phase with anhydrous magnesium sulfate, filter, and spin the obtained filtrate to dry. After blending, the sensitive aspirin prodrug was obtained by separation and purification by column chromatography (dichloro:ethyl acetate=10:1 to dichloro:methanol=15:1). Using deuterated chloroform as solvent, NMR analysis was carried out on the obtained sensitive aspirin prodrug.

[0254] See results figure 1 , figure 1 For the sensitive aspirin prodrug that embodiment 1 prepares 1 H NMR spectrum.

[0255] from figure 1 It can be seen that the peak positi...

Embodiment 2

[0257]

[0258] Dissolve 2g (12.3mmol of repeating units) of dextran in 40mL of anhydrous dimethyl sulfoxide (DMSO), stir to dissolve and add 0.75g (15.4mmol) of 4-dimethylaminopyridine and 0.37g (15.4mmol) of dimethicone Hydrogen-2,5-furandione was sealed and reacted with stirring for 48 hours at a temperature of 30°C. After the reaction, the resulting reaction solution was settled into 400 mL of ice ethanol, filtered, and vacuum-dried at room temperature for 4 hours. After reconstitution in water, the pH 7.4 phosphate buffer was dialyzed for 72 hours, and then freeze-dried to obtain the intermediate product Carboxydextran.

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Abstract

The invention provides an aspirin derivative. The aspirin derivative has a structure as shown in a formula (I) which is described in the specification. The aspirin prodrug with the structure has the capability of sensitively releasing aspirin or salicylic acid under the stimulation of active oxygen or ultraviolet light; furthermore, the sensitive aspirin prodrug with the structure is combined to aspecific polymer carrier; an obtained bonding drug can be enriched to tumor tissues and rapidly release the drug, so that the bonding drug has a wide development prospect in the fields of reducing inflammation of the tumor tissues, improving a tumor immunosuppression microenvironment and inhibiting tumor growth. The aspirin polymer prodrug provided by the invention can be enriched at a tumor or inflammatory site, improve the in-vivo metabolic pathway of aspirin, and can effectively solve the problems of short action time and poor curative effect of micromolecular aspirin. Moreover, the preparation method provided by the invention is simple, wide in raw material source and capable of realizing batch production and industrialization.

Description

technical field [0001] The invention belongs to the technical field of preparation of aspirin derivatives, in particular to an aspirin derivative and its preparation method, medicine and application, especially to a sensitive aspirin prodrug and its preparation method, an aspirin polymer prodrug and its Applications in preparation methods, medicines, anti-tumor or inflammatory diseases. Background technique [0002] Tumor refers to the neogrowth formed by the proliferation of local tissue cells in the body under the action of various tumorigenic factors, because this neogrowth is mostly in the form of space-occupying blocky protrusions, also known as neoplasm (neoplasm) . According to the cell characteristics of new organisms and the degree of harm to the body, tumors are divided into two categories: benign tumors and malignant tumors, and cancer is the general term for malignant tumors. There are many types of cancer, which seriously threaten human health. They have diffe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C08B37/02A61K47/54A61K47/61A61K31/616A61P35/00A61P29/00
CPCA61K31/616A61K47/54A61K47/61A61P29/00A61P35/00C07F5/025C08B37/0009
Inventor 宋万通马胜司星辉徐玉迪姚浩琛汤朝晖陈学思
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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