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Anti-oxidizing derivative of aspirin and its synthetic method and use

A technology for aspirin and a synthesis method is applied in the field of antioxidant derivatives of aspirin and the synthesis thereof, and can solve the problems such as failure to completely solve the gastrointestinal injury of NSAIDs and the like

Inactive Publication Date: 2005-05-18
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, none of the above technologies can completely solve the problem of gastrointestinal damage caused by NSAIDs

Method used

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  • Anti-oxidizing derivative of aspirin and its synthetic method and use
  • Anti-oxidizing derivative of aspirin and its synthetic method and use
  • Anti-oxidizing derivative of aspirin and its synthetic method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010] Example 1: Synthesis of 2-acetoxy-benzoic acid-2-[3-(4-acetoxy-phenyl)-acryloyloxy]-ethyl ester (hereinafter referred to as compound 1)

[0011] step one:

[0012]

[0013] Aspirin Compound 3

[0014] Take 5mmol aspirin and 40mmol thionyl chloride to react at 70°C for 2h, then distill off excess thionyl chloride under reduced pressure. The obtained aspirinyl chloride was dissolved in 10 mL of acetone, and added dropwise to the acetone solution in which 20 mmol of ethylene glycol and 0.012 mol of triethylamine were dissolved (0□). 0□Continue to react at room temperature for 1h after reacting for 1h. After the solvent was evaporated, 0.63 g of compound 2-acetoxy-benzoic acid-2-hydroxy-ethyl ester (hereinafter referred to as compound 3) was obtained as yellow oil, with a yield of 56.0%. Physical constants and spectral data of compound 3: R f 0.18 (petroleum ether / ethyl acetate, 1:1). IR(KBr)cm -1 : 3519, 1769, 1723, 1607, 1580, 1485, 1453. 1 H NMR (CDCl 3 ...

Embodiment 2

[0023] Example 2: 2-acetoxy-benzoic acid-2-[3-(3-methoxy-4-acetoxy-phenyl)-acryloyloxy]-ethyl ester (hereinafter referred to as compound 2) synthesis

[0024] step one:

[0025]

[0026] Compound 5 Compound 7

[0027] Dissolve 0.08 mol of sodium hydroxide in 30 mL of water, ice-bath to below 10°C, add 0.03 mol of 4-hydroxy-3-methoxyphenylacrylic acid (hereinafter referred to as compound 5) under the protection of argon, and stir until dissolved. Slowly add 0.0375mol acetic anhydride dropwise. After the addition, return to room temperature and react for 1 h, acidify to pH 2-3 with 10% sulfuric acid, filter, wash the filter cake four times with water and recrystallize with ethanol to obtain light yellow solid 4-acetoxy-3-methoxyphenylacrylic acid ( Hereinafter referred to as compound 7) 8.83g, yield 87.6%, R f 0.43 (chloroform:methanol, 6:1). The feeding ratio of the sodium hydroxide to the compound 5 is 2-20:1 (molar ratio). The feed ratio of the acetic anhydrid...

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Abstract

Aspirin and phenol antioxidant p-hydroxyphenyl acrylic acid or ferulic acid are used as materials to prepare two kinds of antioxidant aspirin derivatives, named separately as 2-acetoxy-benzoic acid-2-[3-(4-acetoxy-phenyl)-acrylyloxy]-acetate and 2-acetoxy-benzoic acid-2-[3-(3-methoxy-4-acetoxy -phenyl)-acrylyloxy]-acetate chemically. The antioxidant aspirin derivatives are used in preparing antiphlogistic medicine.

Description

technical field [0001] The invention relates to an antioxidant derivative of aspirin and its synthesis method and application. The derivative has inhibitory activity on mouse ear edema caused by croton oil, and can be used to prepare anti-inflammatory drugs. Background technique [0002] Non-steroidal anti-inflammatory drugs, NSAIDs for short, are a class of excellent anti-inflammatory and anti-rheumatic drugs, among which aspirin is the earliest and most widely used NSAIDs. However, NSAIDs have side effects such as severe gastrointestinal damage. According to reports, 15%-30% of long-term users of NSAIDs have varying degrees of gastrointestinal damage. Various efforts have been made to find NSAIDs that do not cause gastrointestinal side effects, including prodrugs, selective COX-2 inhibitors, and nitric oxide-type NSAIDs. However, none of the above techniques can completely solve the problem of gastrointestinal damage caused by NSAIDs. Contents of the invention [000...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/216A61P29/00C07C69/76
Inventor 李英霞于凌波张一纯李春霞
Owner OCEAN UNIV OF CHINA
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