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Anti-novel coronavirus naphthoquinone compound and medical application thereof

A technology of coronaviruses and compounds, applied in the field of medicine, to achieve good prospects for new drug development, high yield, and easy availability of raw materials

Active Publication Date: 2020-06-05
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, no active ingredients of natural medicines have been proven to have clear anti-2019-nCoV activity

Method used

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  • Anti-novel coronavirus naphthoquinone compound and medical application thereof
  • Anti-novel coronavirus naphthoquinone compound and medical application thereof
  • Anti-novel coronavirus naphthoquinone compound and medical application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0024] This embodiment relates to a preparation method of 5-hydroxy-1,4-naphthoquinone (II-1) having structural formula (II), comprising the following steps:

[0025]

[0026] Add 75mL 30% H to a 250mL three-necked bottle 2 o 2 , stirred and added dropwise 42mL of acetic anhydride, and kept the temperature of the reaction solution not exceeding 40°C during the dropwise addition. After dropping, stir at 40°C for 4 hours. Afterwards, 100 mL methanol solution of 1,5-dihydroxynaphthalene (15 g, 93.7 mmol) was added dropwise to the reaction solution under vigorous stirring, and the rate of addition was controlled so that the temperature of the reaction solution did not exceed 60°C. Continue to stir for 1 hour after the dropwise addition, pour into ice water after cooling, a large amount of tan precipitate precipitates, filter and dry to obtain a dark red solid powder. Silica gel column chromatography (mobile phase: ethyl acetate-petroleum ether volume ratio: 1:5) was used for...

Embodiment 2

[0028] This embodiment relates to a preparation method of 5-methoxy-1,4-naphthoquinone (juglone methyl ether) (II-2) having structural formula (II), comprising the following steps:

[0029]

[0030] Compound II-1 (3g, 17.2mmol) described in Example 1 was dissolved in 90mL of THF-H 2 To the O (2:1) mixed solution, tetrabutylammonium bromide (1.6g, 5.2mmol), sodium hydroxide (11.2g, 64.3mmol) and sodium hydroxide (9.6g, 240mmol) were sequentially added under stirring. Gabby, in N 2Under protection, dimethyl sulfate (10 mL, 103 mmol) was added dropwise. After the dropwise addition was completed, react at room temperature for 4 h and post-treatment. The reaction solution was extracted with ethyl acetate (80 mL×3), and the organic layers were combined; the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (mobile phase: ethyl acetate-petroleu...

Embodiment 3

[0032] This embodiment relates to a preparation method of 5-acetoxy-1,4-naphthoquinone (5-acetyljuglone) (III-1) having the structural formula (III), comprising the following steps:

[0033]

[0034] Compound II-1 (3 g, 17.2 mmol) described in Example 1 was dissolved in 10 mL of acetic anhydride, and 5 drops of concentrated sulfuric acid were added dropwise with stirring. The reaction solution was placed in an ice-water bath and stirred for 2 hours. Afterwards, the reaction solution was suction-filtered, washed with ice water and a small amount of methanol successively to obtain about 3.4 g of compound III-1 in the form of light yellow powder crystals, and the yield was 91%. 1 H NMR (4 00MHz, CDCl 3 ): δ8.05(dd, J=7.9, 1.0Hz, 1H), 7.77(t, J=7.9Hz, 1H), 7.40(dd, J=7.9, 1.0Hz, 1H), 6.95(d, J= 10.3Hz,1H),6.85(d,J=10.3Hz,1H),2.45(s,3H,CH 3 CO).

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Abstract

The invention discloses an anti-novel coronavirus naphthoquinone compound and a medical application of the naphthoquinone compound. The structure of the compound is shown as a formula (I), wherein R1is hydrogen, methyl, ethyl, acetyl or propionyl; and R2 is hydrogen, methyl or ethyl. The compound disclosed by the invention has very strong activity of resisting the novel coronavirus, and can be used for inhibiting 3CL hydrolase (3C-like proteinase, 3CLpro) of the 2019-nCoV novel coronavirus. The in-vitro activity determination experiments show that the enzyme inhibition rate of part of the compounds reaches 99% under the concentration of 1 [mu] M. The naphthoquinone compound disclosed by the invention is clear in structure, simple and convenient in preparation method and high in yield, andhas important significance for developing efficient and low-toxicity novel anti-novel coronavirus drugs.

Description

technical field [0001] The invention belongs to the field of medicine, and relates to a naphthoquinone compound against novel coronavirus and its medical application; more specifically, it relates to a naphthoquinone compound based on natural juglone structure and its preparation for anti-2019-2019-2019 coronavirus Uses in medicine for nCoV. Background technique [0002] The 2019 novel coronavirus (2019-nCoV) is an enveloped, positive-sense, single-stranded RNA coronavirus that can cause acute viral pneumonia and can be transmitted from person to person, posing a great threat to public health. The National Health Commission of the People's Republic of China has designated the acute respiratory disease caused by this virus infection as a legal Class B infectious disease, and it shall be managed according to Class A (Disease Prevention and Control Bureau, "Announcement of the National Health Commission of the People's Republic of China", January 2020 20). At present, the cli...

Claims

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Application Information

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IPC IPC(8): C07C50/32A61K31/122A61P31/14
CPCA61P31/14C07C50/32
Inventor 贾金平崔家华
Owner SHANGHAI JIAO TONG UNIV
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