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Acylthiourea neuraminidase inhibitor as well as preparation and application thereof

A technology of neuraminidase and acylthiourea, which is applied in the directions of antiviral agents and organic chemistry, can solve the problems of expensive raw materials for Tamiflu production and complex synthesis process, and achieves good neuraminidase inhibitory activity and simple synthesis method. , the effect of excellent neuraminidase inhibitory effect

Active Publication Date: 2021-02-26
SHANGHAI INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently the most widely used anti-influenza drug is Tamiflu, but with the widespread use of the drug, the resistance of influenza viruses to Tamiflu also appears, and the production raw materials of Tamiflu are extremely expensive and the synthesis process is complicated

Method used

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  • Acylthiourea neuraminidase inhibitor as well as preparation and application thereof
  • Acylthiourea neuraminidase inhibitor as well as preparation and application thereof
  • Acylthiourea neuraminidase inhibitor as well as preparation and application thereof

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preparation example Construction

[0046] Described preparation method specifically comprises the following steps:

[0047] (1) substituted benzaldehyde and malonic acid are formed into a reaction system, and after the reaction, the intermediate of formula (II) is obtained through aftertreatment;

[0048] (2) The intermediate of formula (II) obtained in step (1) and thionyl chloride are dissolved in an organic solvent to form a reaction system, and the intermediate of formula (III) is obtained after the reaction;

[0049] (3) the intermediate of formula (III) obtained in step (2) and ammonium thiocyanate are dissolved in an organic solvent to form a reaction system, and after the reaction, the intermediate of formula (IV) is obtained through aftertreatment;

[0050] (4) The formula (IV) intermediate obtained in step (3) and 3-amino-4-methoxybenzoic acid methyl ester are dissolved in an organic solvent to form a reaction system, and after the reaction, the intermediate of formula (V) is obtained through post-tre...

Embodiment

[0059] A preparation method containing an acylthiourea neuraminidase inhibitor, the structural formula of which is shown in Formula A:

[0060] That is, Ar is

[0061] Concrete synthetic steps are as follows:

[0062] (1) Accurately weigh 1.67g (10mmol) of 3-hydroxyl-4-nitrobenzaldehyde and 1.04g (10mmol) of malonic acid in a 50mL round bottom flask, add 20mL absolute ethanol, then add dropwise a catalytic amount (1 drops) of piperidine. After the dropwise addition, take out the round-bottomed flask, place it in a constant temperature oil bath at 85°C to heat and stir for 2 hours, take it out and cool the reaction solution, adjust the pH to 3 with hydrochloric acid and let stand to precipitate a large amount of precipitate, filter the precipitate to obtain a filter cake, filter The cake is washed many times with a large amount of ice water, then dried in a vacuum oven, and recrystallized from ethanol to obtain the intermediate of formula (II) (wherein Ar is ).

[0063...

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Abstract

The invention relates to an acylthiourea neuraminidase inhibitor as well as preparation and application thereof, and the inhibitor has a structure as shown in a formula (I), wherein Ar is show in thespecification. The preparation method specifically comprises the following steps: (1) reacting substituted benzaldehyde with malonic acid, and carrying out aftertreatment to obtain an intermediate asshown in a formula (II); (2) dissolving the intermediate shown as the formula (II) and thionyl chloride into an organic solvent, and conducting reacting to obtain an intermediate shown as a formula (III); (3) dissolving the intermediate as shown in the formula (III) and ammonium thiocyanate in an organic solvent, conducting reacting, and carrying out aftertreatment to obtain an intermediate as shown in a formula (IV); (4) dissolving the intermediate as shown in the formula (IV) and methyl 3-amino-4-methoxybenzoate in an organic solvent, reacting, and carrying out aftertreatment to obtain an intermediate as shown in a formula (V); and (5) hydrolyzing the intermediate shown in the formula (V), and carrying out aftertreatment to obtain the inhibitor shown in the formula (I). Compared with theprior art, the compound is novel in structure, and experiments show that the compound has good neuraminidase inhibitory activity and can be used for preparing drugs for inhibiting neuraminidase activity.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and in particular relates to an acylthiourea neuraminidase inhibitor and its preparation and application. Background technique [0002] Neuraminidase is a glycoprotein distributed on the envelope of influenza virus, which can assist mature influenza virus to escape from the original host cells and infect new cells. Therefore, neuraminidase is one of the important targets for the development of anti-influenza virus drugs one. [0003] Anti-influenza drugs developed by targeting neuraminidase can be divided into the following categories according to their structures: cyclohexenes, pyrans, pyrrolidines, benzoic acid derivatives, and natural products. Currently the most widely used anti-influenza drug is Tamiflu, but with the widespread use of the drug, the resistance of influenza viruses to Tamiflu also appears, and the production raw materials of Tamiflu are extremely expensive and the synthes...

Claims

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Application Information

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IPC IPC(8): C07C335/26A61P31/16
CPCC07C335/26A61P31/16
Inventor 程利平傅世凯钟志坚石林余微庞婉
Owner SHANGHAI INSTITUTE OF TECHNOLOGY
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