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Application of polycyclic polyketone compound in preparation of medicine for resisting novel coronavirus

A technology of polyketide compounds and coronaviruses, which can be used in antiviral agents, pharmaceutical formulations, medical preparations containing active ingredients, etc., and can solve the problem of lack of anti-SARS-CoV-2 drugs

Active Publication Date: 2021-05-04
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is currently no preventive vaccine against SARS-CoV-2 infection, and most vaccines are still in clinical research
In addition, there is a lack of specific anti-SARS-CoV-2 drugs clinically
Clinically reported interferon, Kaletra and some traditional Chinese medicines have therapeutic effects on pneumonia caused by the new coronavirus, but the antiviral effects of these drugs still need further confirmation

Method used

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  • Application of polycyclic polyketone compound in preparation of medicine for resisting novel coronavirus
  • Application of polycyclic polyketone compound in preparation of medicine for resisting novel coronavirus
  • Application of polycyclic polyketone compound in preparation of medicine for resisting novel coronavirus

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] 6,8-Hydroxy-5-(3-methylbutyryl)-9-isobutyl-2,2,4,4-tetramethyl-4,9-dihydro-1H-xanthene-1, Preparation of 3(2H)-diketone (1)

[0050]

[0051] first step

[0052] Dissolve phloroglucinol 26a (2.5 g, 20 mmol) in nitromethane solution at room temperature, add anhydrous aluminum chloride (10.7 g, 80 mmol) and isobutyryl chloride (2.3 g, 22 mmol) successively , and warmed to reflux. After reacting for 12 hours, the reaction solution was slowly poured into ice water, and saturated sodium potassium tartrate solution (100 mL) was added, followed by vigorous stirring. The reaction solution was extracted 3 times with ethyl acetate (100 mL×3). The organic phases were combined and washed with saturated NaCl solution. After drying and filtering over anhydrous sodium sulfate, the organic phase was evaporated to dryness under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography to obtain compound 26c (3.6 g, yield 85%).

...

Embodiment 2

[0061] 6,8-Dihydroxy-5-(2-diylbutyryl)-9-isopropyl-2,2,4,4-tetramethyl-4,9-dihydro-1H-xanthene-1 , Preparation of 3(2H)-diketone (2)

[0062]

[0063] Compound 27b (1.0 g, 5 mmol) was dissolved in THF and added to compound 27a (1.8 g, 7.5 mmol) at room temperature. After reacting for 4 hours, p-toluenesulfonic acid monohydrate (2.9 g, 15 mmol) was added, and the temperature was raised to reflux. After reacting for 2 hours, cool down to room temperature, add saturated aqueous sodium bicarbonate (100 mL) to quench the reaction, and extract the reaction solution with ethyl acetate three times (100 mL×3). The organic phases were combined and washed with saturated NaCl solution. After drying and filtering over anhydrous sodium sulfate, the organic phase was evaporated to dryness under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography to obtain compound 2 (964 mg, yield 45%).

[0064] 1 H NMR (500 MHz, CDCl 3 ) δ 13....

Embodiment 3

[0066] 6,8-Dihydroxy-5-(2-methylbutyryl)-9-phenyl-2,2,4,4-tetramethyl-4,9-dihydro-1H-xanthene-1, Preparation of 3(2H)-diketone (3)

[0067]

[0068]Compound 27b (1.0 g, 5 mmol) was dissolved in THF and added to compound 28a (2.0 g, 7.5 mmol) at room temperature. After reacting for 4 hours, p-toluenesulfonic acid monohydrate (2.9 g, 15 mmol) was added, and the temperature was raised to reflux. After reacting for 2 hours, cool down to room temperature, add saturated aqueous sodium bicarbonate (100 mL) to quench the reaction, and extract the reaction solution with ethyl acetate three times (100 mL×3). The organic phases were combined and washed with saturated NaCl solution. After drying and filtering over anhydrous sodium sulfate, the organic phase was evaporated to dryness under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography to obtain compound 3 (994 mg, yield 43%).

[0069] 1 H NMR (400 MHz, CDCl 3 ) δ 13.50 ...

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Abstract

The invention discloses an application of a polycyclic polyketone compound in preparation of a medicine for resisting a novel coronavirus SARS-CoV-2. The polyketone compound disclosed by the invention has an inhibition effect on a novel coronavirus SARS-CoV-2 at a cellular level, can be used for remarkably reducing the virus titer of the virus in cells and inhibiting cytopathy induced by the virus, and has concentration dependence. In addition, the polyketone compound has chemical structure types different from those of the ridecevir and the chloroquine phosphate, and is expected to be developed into a novel medicine for resisting the novel coronavirus SARS-CoV-2. Therefore, the compound has a good application prospect in treatment of related diseases caused by infection of novel coronavirus SARS-CoV-2.

Description

technical field [0001] The present invention relates to a class of medicines for treating and preventing virus infection. More specifically, the present invention relates to the application of a class of polycyclic polyketide compounds in the preparation of anti-new coronavirus SARS-CoV-2 drugs. Background technique [0002] The 2019 novel coronavirus (SARS-CoV-2) is an RNA virus with an envelope and a linear single-stranded positive strand genome, which mainly causes pneumonia and severe acute respiratory syndrome (COVID-19), which can be accompanied by renal failure and even die. SARS-CoV-2 is mainly transmitted through respiratory droplets or direct contact with secretions, and there is also evidence that it can be transmitted through aerosol and fecal-oral routes. Its transmission speed is fast and wide, and it seriously threatens human health and life. There is currently no preventive vaccine against SARS-CoV-2 infection, and most vaccines are still in the clinical ...

Claims

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Application Information

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IPC IPC(8): A61K31/352A61P31/14
CPCA61K31/352A61P31/14
Inventor 叶文才王英胡利军唐维李药兰张冬梅范春林
Owner JINAN UNIVERSITY
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