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Nucleophilic N0 donor of alkyl modified amido glucose, and synthetic method

A technology of glucosamine and alkyl modification, which is applied in the field of medical engineering, can solve the problems of insufficient NO response, low NO load, and low NO load, so as to improve antithrombotic performance, promote wound healing, and prevent restenosis Effect

Inactive Publication Date: 2008-09-03
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its shortcoming is that the loading degree of NO is low, and reason has two points: (1) the degree of substitution of chitosan amino modification (carboxylation and alkylation) generally only has 25-27%, and low degree of substitution causes NO very low load
(2) The reaction of chitosan modified product with NO is a heterogeneous reaction, so that NO can not fully react
thus limiting its use in medicine

Method used

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  • Nucleophilic N0 donor of alkyl modified amido glucose, and synthetic method
  • Nucleophilic N0 donor of alkyl modified amido glucose, and synthetic method
  • Nucleophilic N0 donor of alkyl modified amido glucose, and synthetic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: the synthesis of propionaldehyde (PA) modified glucosamine / NO

[0026] Add 10g (0.0506mol) of glucosamine hydrochloride (GS) into 100ml of methanol solution, add 50ml of water to dissolve it, add 5.5ml of propionaldehyde (GS:PA molar ratio 1:1.5) into the system, and react at room temperature for 12h , 3.83 383g (0.1012mol, GS: NaBH 4 The molar ratio of = 1:2) NaBH 4 Dissolve in 25ml of water, slowly drop into the solution, reduce for 12 hours to obtain a light yellow solution, use 100ml of acetone to precipitate viscous substances, filter, and the filtrate is rotary evaporated, and the obtained solid is heated and dissolved with methanol, then filtered, and the product is purified with methanol repeatedly , and finally dried to obtain 5 g of light yellow crystal powder.

[0027] Add 2.5g (0.01mol) of the above reaction product to 100ml of anhydrous methanol solution containing 2.15g (0.02mol) sodium methoxide, react with NO in an autoclave, maintain the...

Embodiment 2

[0029] Embodiment 2: the synthesis of glutaraldehyde modified glucosamine hydrochloride / NO

[0030] 10g (0.0506mol) glucosamine hydrochloride (GS) was added in the methanol solution of 100ml, 20.24g 25% glutaraldehyde aqueous solution (GS: the molar ratio of glutaraldehyde=1: 1) was added in the solution, room temperature reaction 24h. 3.83g (0.1012mol, GS: NaBH 4 The molar ratio of = 1:2) NaBH 4Dissolve in 25ml of water, slowly drop into the solution, reduction reaction 12h. After the reaction is completed, add 30ml of water to the reaction solution, place it in a water bath at 50-60°C and stir for a period of time, the solution will gradually become transparent, and a white sticky precipitate will form when placed at room temperature, filter through filter paper, add 30ml of acetone to the filtrate, and dry the filtrate at 60°C Dry to give 8.1210 g of yellow powder. The product was dissolved in methanol and filtered, and the filtrate was dried to obtain 7.0 g of light ye...

Embodiment 3

[0033] Embodiment 3: the synthesis of n-chlorobutane modified glucosamine hydrochloride / NO donor

[0034] 10g (0.0506mol) glucosamine hydrochloride (GS) was added to 100ml of 10% isopropanol aqueous solution, stirred at 70°C for 30 minutes, and chlorobutane was added dropwise, wherein halogenated hydrocarbon: glucosamine salt The molar ratio of acid salt is 1:1-1.2, react at room temperature for 12 hours, neutralize the solution with hydrochloric acid to neutrality, and rotate to evaporate. About 5g of light yellow crystal powder.

[0035] Add 1 g (0.004 mol) of the above reaction product into 100 ml of anhydrous methanol solution containing 0.86 g (0.008 mol) of sodium methylate, react with NO in an autoclave, maintain the pressure at 5 atm, and react for 3 days. Washed with water, methanol and ether, and dried under vacuum at room temperature to obtain about 1 g of white fluffy powder.

[0036] Determination of [N(O)NO] by UV Spectroscopy - The specific absorption of the ...

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Abstract

This invention discloses a method for synthesizing alkyl-modified amino glucose as a nucleophilic NO donor. The method comprises: performing alkyl-modification on the NH2 groups of amino glucose to form nucleophilic NH groups, and reacting with NO molecules in sodium methoxide / methanol solution under 5 atm for 5 d to form [N(O)NO]- groups. The chemical formula of alkyl-modified amino glucose is shown in the formula. The obtained alkyl-modified amino glucose nucleophilic NO donor has different NO releasing rate and long half life, can overcome cytotoxicity of nucleophilic reagent and avoid the formation of oncogenic byproduct of nitrosamine, and have important clinical applications.

Description

technical field [0001] The invention relates to a drug in the technical field of medical engineering and a synthesis method thereof, in particular to an alkyl-modified glucosamine nucleophilic NO donor and a synthesis method thereof. Background technique [0002] Contains [N(O)NO] - Compounds with functional groups are one of the most important NO donor drugs developed in recent years. It can release NO molecules spontaneously under physiological conditions; after being replaced by O2, it can be detached by specific enzymes in target organs and target cells, and has targeted functions; it also has good controllability; in addition, it can It is prepared into various forms and applied in different medical fields according to needs. Although a large number of in vitro tests have proved that it can effectively prevent restenosis after plastic surgery, improve the antithrombotic performance of medical devices, relieve pulmonary hypertension and vasospasm, etc., but the cytotox...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H5/06
Inventor 万锕俊高群
Owner SHANGHAI JIAO TONG UNIV
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