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Benzisoselenazolone derivative, preparation method and application in anti-coronavirus drugs

A technology of benzisoselenazolone and benzisoselenazole, applied in the field of anti-coronavirus drug discovery, can solve problems such as lack of targeted Mpro active compounds

Pending Publication Date: 2020-12-22
QINGDAO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Through the above analysis, the existing problems and defects of the prior art are: there is still a lack of active compounds targeting Mpro as candidates for drug research

Method used

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  • Benzisoselenazolone derivative, preparation method and application in anti-coronavirus drugs
  • Benzisoselenazolone derivative, preparation method and application in anti-coronavirus drugs
  • Benzisoselenazolone derivative, preparation method and application in anti-coronavirus drugs

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preparation example Construction

[0130] Such as figure 1 As shown, the preparation method of the benzisoselenazolon derivative provided by the invention comprises the following steps:

[0131] S101: Synthesis of o-iodobenzamide derivatives. Dissolve the corresponding o-iodobenzoic acid in dry dichloromethane, then add 4-dimethylaminopyridine (DMAP) and aromatic amine to the above solution, and finally add 1-(3-dimethylaminopropyl)- 3-Ethylcarbodiimide hydrochloride (EDC·HCl), stirred overnight at room temperature. The reaction solution was concentrated and purified by column chromatography to obtain o-iodobenzamide derivatives. The molar ratio of o-iodobenzoic acid, arylamine, DMAP, and EDC is 1:1.1:0.2:1.4.

[0132] S102: Preparation of benzisoselenazolone derivatives. The corresponding o-iodobenzamide derivatives, potassium selenocyanate cuprous iodide, 1,10-phenanthroline and cesium carbonate were dissolved in DMF, and stirred and reacted at 110°C for 2 hours under the protection of nitrogen. The rea...

Embodiment 1

[0136] Embodiment 1: Preparation of representative compound EB2-1 of benzisoselenazolone derivative

[0137]

[0138] Dissolve 2-iodo-benzoic acid (5 mmol) in dry dichloromethane, then add 4-dimethylaminopyridine (DMAP, 1 mmol) and 4-aminoaniline (5.5 mmol) to the above solution, and finally add 1 -(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC·HCl, 7 mmol), stirred overnight at room temperature. The reaction solution was concentrated and purified by column chromatography to obtain 2-iodo-N-(4-aminophenyl)benzamide.

[0139] 2-iodo-N-(4-aminophenyl)benzamide (1.3mmol), potassium selenocyanate (1.56mmol), cuprous iodide (1.95mmol), 1,10-phenanthroline (1.95mmol) 1. Cesium carbonate (3.25 mmol) was dissolved in 3 ml of DMF, and stirred and reacted at 110° C. for 2 hours under the protection of nitrogen. The reaction solution was extracted with ethyl acetate, washed with water, dried, concentrated, and subjected to column chromatography to obtain the ebselen ...

Embodiment 2

[0140] Embodiment 2: Preparation of representative compound EB2-3 of benzisoselenazolone derivative

[0141]

[0142] Dissolve 2-iodobenzoic acid (5mmol) in dry dichloromethane, then add 4-dimethylaminopyridine (DMAP, 1mmol) and 3-aminoaniline (5.5mmol) to the above solution, and finally add 1- (3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC·HCl, 7 mmol), stirred overnight at room temperature. The reaction solution was concentrated and purified by column chromatography to obtain 2-iodo-N-(3-aminophenyl)benzamide.

[0143] 2-iodo-N-(3-aminophenyl)benzamide (1.3mmol), potassium selenocyanate (1.56mmol), cuprous iodide (1.95mmol), 1,10-phenanthroline (1.95mmol) 1. Cesium carbonate (3.25 mmol) was dissolved in 3 ml of DMF, and stirred and reacted at 110° C. for 2 hours under the protection of nitrogen. The reaction solution was extracted with ethyl acetate, washed with water, dried, concentrated, and subjected to column chromatography to obtain the ebselen seri...

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Abstract

The invention belongs to the technical field of anti-coronavirus drug discovery, discloses a benzisoselenazolone derivative, a preparation method and application of the benzisoselenazolone derivativein coronavirus resistance, and relates to synthesis of an o-iodobenzamide derivative. The preparation method of the benzisoselenazolone derivative comprises the following steps: dissolving a corresponding o-iodobenzamide derivative, potassium selenocyanate, cuprous iodide, 1,10-phenanthroline and cesium carbonate in DMF, carrying out stirring reaction under the protection of nitrogen, conducting extracting on the reaction solution with ethyl acetate, conducting washing with water, conducting drying and concentrating, and carrying out column chromatography to obtain the benzisoselenazolone derivative. The invention aims to develop an anti-coronavirus drug with stronger 3CL protease inhibition activity, higher antiviral activity and low toxicity. The invention provides an application of thebenzisoselenazolone derivative in the aspect of coronavirus resistance, and relates to an application of the benzisoselenazolone derivative in preparing a medicine for preventing or / and resisting coronavirus, and a medicine composition for preventing or / and resisting coronavirus.

Description

technical field [0001] The invention belongs to the technical field of discovery of anti-coronavirus drugs, and in particular relates to a benzisoselenazolon derivative, a preparation method and an application in anti-coronavirus drugs. Background technique [0002] At present: The new coronavirus has been identified as SARS-CoV-2, which has broken out and spread globally. SARS-CoV-2 has a strong infectious ability. The infected person will have severe acute respiratory infection symptoms, and severe cases will also have pulmonary edema. Death from ARDS or multiple organ failure. Although the health and medical departments of various countries have taken active measures to deal with the epidemic, due to the lack of specific therapeutic drugs, it is still unable to effectively prevent the spread of SARS-CoV-2 and the casualties caused by infection. [0003] 3CL protease (Mpro) is the main protease of SARS-CoV-2 and plays an important role in mediating viral replication and t...

Claims

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Application Information

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IPC IPC(8): C07D293/10C07D421/04A61K31/41A61K31/4439A61P31/14
CPCC07D293/10C07D421/04A61P31/14Y02A50/30
Inventor 张延如卫宁宁乔振王克威
Owner QINGDAO UNIV
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