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1,3,4-oxadiazole derivative containing glucosamine molecules and preparation method and application thereof

A technology of oxadiazole and glucose, which is applied in the field of drug preparation, can solve the problems of narrow substrate use range, harsh reaction conditions, and long cyclization time, and achieve the effects of low price, easy post-processing, and strong inhibitory activity

Inactive Publication Date: 2016-04-20
HUAIHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

All of the reagents used above have one or more disadvantages, such as harsh reaction conditions, long cyclization time, more by-products, expensive catalysts, narrow use range of substrates, and unfriendly to the environment, etc.

Method used

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  • 1,3,4-oxadiazole derivative containing glucosamine molecules and preparation method and application thereof
  • 1,3,4-oxadiazole derivative containing glucosamine molecules and preparation method and application thereof
  • 1,3,4-oxadiazole derivative containing glucosamine molecules and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1, a kind of 1,3,4-oxadiazole derivative containing glucosamine molecule, its molecular formula is as follows:

[0025]

[0026] Wherein, the R is selected from -CH 3 ,-C 2 h 5 ,-C 4 h 11 ,-C 6 h 5 ,-C 5 h 4 N,4-OHC 6 h 4 -,3-CH 3 C 6 h 4 , 4-CH 3 C 6 h 4 ,3-CH 3 OC 6 h 4 -,2-NO 2 C 6 h 4 -,4-NO 2 C 6 h 4 -, 2-FC 6 h 4 -,4-FC 6 h 4 -,2-ClC 6 h 4 -,3-ClC 6 h 4 -,3-BrC 6 h 4 -,4-IC 6 h 4 -,4-N(CH 3 ) 2 C 6 h 4 ,-C 4 h 3 S,-C 4 h 3 O.

Embodiment 2

[0027] Embodiment 2, a kind of synthetic method of the 1,3,4-oxadiazole derivative containing glucosamine molecule as described in embodiment 1, its steps are as follows:

[0028] (1) Preparation of 2-deoxy-2-isothiocyanate-1,3,4,6-tetra-O-benzyl-β-D-glucopyranose: 2-deoxy-2-amino-1 ,3,4,6-Tetra-O-benzyl-β-D-pyranose hydrochloride, carbon disulfide and triethylamine are reacted, and then reacted with p-toluenesulfonyl chloride to obtain 2-deoxy-2-isothiocyanate Ester-1,3,4,6-tetra-O-benzyl-β-D-glucopyranose; reaction with acetonitrile as solvent, 2-deoxy-2-amino-1,3,4,6-tetra- The molar ratio of O-benzyl-β-D-pyranose hydrochloride to carbon disulfide, triethylamine and p-toluenesulfonyl chloride is 1:1:3:1, the reaction temperature is 0°C, and the reaction time is 1 hour;

[0029] (2) N-(1,3,4,6-tetra-O-benzyl-β-D-glucopyranose-2-yl)-2-amino-5-substituted-1,3,4-oxadi Preparation of azole: first react 2-deoxy-2-isothiocyanate-1,3,4,6-tetra-O-benzyl-β-D-glucopyranose with hydr...

Embodiment 3

[0030] Embodiment 3, a kind of synthetic method of the 1,3,4-oxadiazole derivative containing glucosamine molecule as described in embodiment 1, its steps are as follows:

[0031] (1) Preparation of 2-deoxy-2-isothiocyanate-1,3,4,6-tetra-O-benzyl-β-D-glucopyranose: 2-deoxy-2-amino-1 ,3,4,6-Tetra-O-benzyl-β-D-pyranose hydrochloride, carbon disulfide and triethylamine are reacted, and then reacted with p-toluenesulfonyl chloride to obtain 2-deoxy-2-isothiocyanate Ester-1,3,4,6-tetra-O-benzyl-β-D-glucopyranose; reaction with acetonitrile as solvent, 2-deoxy-2-amino-1,3,4,6-tetra- The molar ratio of O-benzyl-β-D-pyranose hydrochloride to carbon disulfide, triethylamine, and p-toluenesulfonyl chloride is 1:1.2:3.3:1.2, the reaction temperature is 0°C, and the reaction time is 1.5 hours;

[0032] (2) N-(1,3,4,6-tetra-O-benzyl-β-D-glucopyranose-2-yl)-2-amino-5-substituted-1,3,4-oxadi Preparation of azole: first react 2-deoxy-2-isothiocyanate-1,3,4,6-tetra-O-benzyl-β-D-glucopyranose...

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Abstract

The invention provides a 1,3,4-oxadiazole derivative containing glucosamine molecules. R in the molecular formula is selected from -CH3, -C2H5, -C4H11, -C6H5, -C5H4N, 4-OHC6H4-, 3-CH3C6H4, 4-CH3C6H4-, 3-CH3OC6H4-, 2-NO2C6H4-, 4-NO2C6H4-, 2-FC6H4-, 4-FC6H4-, 2-ClC6H4-, 3-ClC6H4-, 3-BrC6H4-, 4-IC6H4-, 4-N (CH3)2C6H4-, -C4H3S, and -C4H3O. The invention further discloses a synthesis method and application of the 1,3,4-oxadiazole derivative containing the glucosamine molecules. The adopted synthesis method has the advantages of being easy and convenient to implement, rapid, high in applicability, efficient and the like. An adopted cyclization reagent has the advantages of being low in price, low in toxicity and the like. The glucosamine molecules are introduced into the 1,3,4-oxadiazole molecules, and the synthesized target compound has the strong inhibitory activity for acetylcholin esterase, thereby having the wide application prospect in the aspect of preparation of anticholinesterase medicine.

Description

technical field [0001] The invention relates to the field of medicine preparation, in particular to a 1,3,4-oxadiazole derivative containing a glucosamine molecule, a preparation method thereof and an application as an acetylcholinesterase inhibitor. Background technique [0002] 1,3,4-Oxadiazoles and their derivatives are an important class of organic heterocyclic compounds. Because these compounds are easy to metabolize in vivo and can be associated in the form of hydrogen bonds, they exhibit many biological activities, such as anti- Fungi, anti-spasmodic, anti-inflammatory, anti-tumor and analgesic, etc., are widely used in medicine and agriculture. [0003] Glucosamine, as an abundant natural monosaccharide, widely exists in human tissues and is a biological precursor for the synthesis of glycoproteins, glycosphingolipids, lipopolysaccharides and hyaluronic acid. Glucosamine itself has many biological activities, such as: anti-tumor, anti-virus, anti-bacterial, improvin...

Claims

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Application Information

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IPC IPC(8): C07H17/00C07H1/00A61K31/7056A61P25/28
CPCC07H17/00C07H1/00
Inventor 刘玮炜程峰昌殷龙史大华刘秀坚
Owner HUAIHAI INST OF TECH
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