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Fullerene galactoside derivative, and preparation method and application thereof

A technology of fullerene and derivatives, applied in the field of fullerene galactose derivatives, can solve the problems of impurity, sample loss, mixed impurities, etc., and achieve the effect of strong removal of superoxide anion free radicals

Inactive Publication Date: 2012-01-04
蚌埠丰原涂山制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the process of preparing fullerene sugar derivatives, the inventors attempted to synthesize the azide sugar by first using galactose for bromination and then azidation in the prior art, but the method for synthesizing azidogalactose Multiple reactions are required, and many samples will be lost due to operational errors in each reaction, and many impurities will be mixed, making the product yield low and impure
Therefore, the preparation process of existing method has many imperfections

Method used

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  • Fullerene galactoside derivative, and preparation method and application thereof
  • Fullerene galactoside derivative, and preparation method and application thereof
  • Fullerene galactoside derivative, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1 The preparation method of fullerene monoaddition and double addition acetylated galactose derivatives

[0038] In a 250ml three-neck round bottom flask, add 56mg 2,3,4,6-O-tetraacetyl-1-azido-beta-D-galactose and 72mg C 60 , 16ml of chlorobenzene, under the protection of argon, the oil bath was refluxed at 131°C for 8 hours. The reaction process was monitored by TLC, and a brown band appeared at Rf=0.6. After the reaction, the solvent was evaporated to dryness, and the solid residue was separated with a silica gel column. When the eluting solution is toluene / ethyl acetate=10 / 1, the monoaddition product of fullerene galactose is obtained; when the eluting solution is toluene / ethyl acetate=5 / 1, the fullerene galactose is obtained The double-addition product; when the eluting solution is toluene, unreacted C 60 . Both mono-addition and double-addition derivatives are brown solids, and the yields are 21.6 mg (16.8%) and 15.6 mg (12.18%), respectively. The ...

Embodiment 2

[0039] Embodiment 2 The preparation method of fullerene monoaddition and double addition acetylated galactose derivatives

[0040] In a 500ml three-neck round bottom flask, add 112mg 2,3,4,6-O-tetraacetyl-1-azido-beta-D-galactose and 144mg C 60 , 32ml of dichloromethane, refluxed in an oil bath at 120°C for 14 hours under the protection of argon. The reaction process was monitored by TLC, and a brown band appeared at Rf=0.6. After the reaction, the solvent was evaporated to dryness, and the solid residue was separated with a silica gel column. When the eluting solution is toluene / ethyl acetate=10 / 1, the monoaddition product of fullerene galactose is obtained; when the eluting solution is toluene / ethyl acetate=5 / 1, the fullerene galactose is obtained The double-addition product; when the eluting solution is toluene, unreacted C 60 . Both mono-addition and double-addition derivatives are brown solids, and the yields are 41.2 mg (16.09%) and 30.2 mg (11.8%), respectively. Th...

experiment example 1

[0041]Experimental Example 1 Detection of Superoxide Anion Free Radical Scavenging Ability in Pyrogallol Autoxidation System

[0042] 1. Principle

[0043] Pyrogallol can rapidly self-oxidize under alkaline conditions, generate a series of intermediate products with strong absorption at 300-325nm, and release superoxide anion (O 2 - ), to detect the rate of change of absorbance at 320nm, which represents the rate of autoxidation of pyrogallol. If a compound that can scavenge superoxide anion is added to the system, the autoxidation rate of pyrogallol will be slowed down. The autoxidation rate of pyrogallol is accelerated if a compound that can generate superoxide anion is added.

[0044] Sample Clear O 2 - The clearance rate (S) is calculated by the following formula:

[0045] S=(K 0 -K 1 ) / K 0 ×100%

[0046] where K 0 represents the standard autoxidation rate of pyrogallol, K 1 Represents the autoxidation rate of the added sample group.

[0047] 2. Experiment

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Abstract

The invention relates to a new polymer compound, namely a fullerene galactoside derivative, which is a fullerene mono- and / or bis-addition acetylated galactoside. The invention also relates to a preparation method for the fullerene galactoside derivative, and application of the fullerene galactoside derivative in removal of free radicals. The fullerene galactoside derivative can make the auto-oxidation rate of pyrogallol reduced, which indicates that the derivative has the capacity of removing super oxygen negative ion free radicals, is a good antioxidant, and is widely applied to the fields of biomedicines and cosmetics.

Description

technical field [0001] The invention relates to fullerene galactose derivatives, in particular to fullerene single and / or double addition acetylated galactose and its preparation method and application. Background technique [0002] Fullerene is the third allotrope of carbon. Its molecule is a closed network cage structure formed by the combination of carbon atoms. Its special cage structure makes it useful in biology, physics, It has good research value in the field of chemistry. Due to the low solubility of fullerene in polar solutions and easy aggregation, it cannot interact with the target molecules of the human body. However, chemical modification of the surface of fullerene, Introducing a hydrophilic group to make the product water-soluble is the best solution. At present, many fullerene derivatives have been synthesized. [0003] The derivatization of fullerenes can not only form amphiphilic molecules, but also have special properties in terms of pharmacokinetics an...

Claims

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Application Information

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IPC IPC(8): C07H19/04C07H1/00A61K31/706A61K31/7052A61P39/06G01N21/33
Inventor 王艳盛太奎李士桥鞠岚岚
Owner 蚌埠丰原涂山制药有限公司
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