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7-substituted deoxygenated vasicinone as well as preparation method and application thereof

A technology of deoxy-duckbillone and nitrodeoxy-duckbilline, applied in nervous system diseases, organic chemistry, drug combination, etc., can solve the problems of complex pathogenesis and difficult to cure diseases, and achieve strong inhibition The effect of action

Inactive Publication Date: 2019-01-18
XINYANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the complex pathogenesis of AD involving many pathways and proteins, single-target drugs only target a single target, and it is difficult to cure this complex disease

Method used

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  • 7-substituted deoxygenated vasicinone as well as preparation method and application thereof
  • 7-substituted deoxygenated vasicinone as well as preparation method and application thereof
  • 7-substituted deoxygenated vasicinone as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] A kind of 7-substituted deoxyrucone base, its structural general formula is as shown in formula I:

[0029]

[0030] In this embodiment, R represents hydrogen.

[0031] The preparation method of above-mentioned 7-substituting deoxyalkalin, comprises the following steps:

[0032] (1) Weigh 4.0g of deoxyalkaline base and place it in a 250mL flask, add a mixed acid of concentrated nitric acid-concentrated sulfuric acid (v / v=3:1) dropwise at 0°C, and react for 3 hours after the addition is completed, and the reaction Pour the mixture into 300mL of ice-water to quench the reaction, adjust the pH to 9 with NaOH aqueous solution, place it in the refrigerator overnight at 0°C, then filter and dry to obtain 4.2g of 7-nitrodeoxyalconine; Add 4.2g of 7-nitrodeoxyalkaline base into a 250mL flask, dissolve it with 70mL of absolute ethanol, and then add 100mL of Na 2 S aqueous solution (containing Na 2 S 8.0g), after heating to reflux for 8h, the ethanol was removed by distilla...

Embodiment 2

[0037] A kind of 7-substituted deoxyrucone base, its structural general formula is as shown in formula I:

[0038]

[0039] In this embodiment, R represents methyl.

[0040] The preparation method of above-mentioned 7-substituting deoxyalkalin, comprises the following steps:

[0041] (1) Weigh 4.0g of deoxyalkaline base and place it in a 250mL flask, add a mixed acid of concentrated nitric acid-concentrated sulfuric acid (v / v=3:1) dropwise at 0°C, and react for 3 hours after the addition is completed, and the reaction Pour the mixture into 300mL of ice-water to quench the reaction, adjust the pH to 9 with NaOH aqueous solution, place it in the refrigerator overnight at 0°C, then filter and dry to obtain 4.2g of 7-nitrodeoxyalconine; Add 4.2g of 7-nitrodeoxyalkaline base into a 250mL flask, dissolve it with 70mL of absolute ethanol, and then add 100mL of Na 2 S aqueous solution (containing Na 2S 8.0g), after heating to reflux for 8h, the ethanol was removed by distillatio...

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Abstract

The invention relates to 7-substituted deoxygenated asicinone, and belongs to the technical of medicine chemistry. A preparation method of the 7-substituted deoxygenation vasicinone comprises the following steps: performing the nitration reaction and reduction reaction on deoxygenated vasicinone serving as an initial raw material to obtain 7-amino deoxygenated vasicinone, enabling the 7-amino deoxygenated vasicinone to make amidation reaction with 3-bromo-propionic acid to obtain 7-(3-bromine propionamide) deoxygenated vasicinone; enabling piperazine to react with benzyl bromide or 2-methyl benzyl bromide to obtain a benzyl or 2-methyl benzyl piperazine compound; and enabling the obtain 7-(3'-bromine propionamide) deoxygenated vasicinone to react with the benzyl or 2-methyl benzyl piperazine compound, thus obtaining the 7-substituted deoxygenation vasicinone. The 7-substituted deoxygenation vasicinone disclosed by the invention has high inhibition effect for acetylcholin esterase, beta-secretase and beta-amyloid protein and is expected to become a multi-target anti-AD candidate drug.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and relates to a preparation method of a class of 7-substituent kabione bases and its application in treating Alzheimer's disease. Background technique [0002] Alzheimer's disease (AD), also known as Alzheimer's disease, is a common chronic neurodegenerative disease (Goedert, M. et al., Science 2006, 314, 777-781; Boddapati, S. et al. , J Mol. Biol 2011, 405, 436-447.). There are about 50 million AD patients in the world, and about 8 million people in my country are plagued by Alzheimer's disease, ranking first in the world, and the number is increasing by 300,000 to 400,000 people every year. AD has become the fourth leading cause of death in the elderly, threatening the health and life of the elderly seriously. At present, there is no satisfactory treatment for AD. The commonly used AD treatment drugs include tacrine and other 4 kinds of acetylcholinesterase inhibitors (AChEIs) a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61P25/28
CPCA61P25/28C07D487/04
Inventor 杜宏涛马芳魏欠欠刘新莲谢居森
Owner XINYANG NORMAL UNIVERSITY