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Rhein derivative and antiviral application thereof

A compound and alkyl technology, applied in the field of rhein-derived compounds and their antiviral applications, can solve the problems that antiviral applications need to be further developed

Active Publication Date: 2021-06-08
CHINA INSPECTION SCI PHARM BEIJING GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Rhein (4,5-dihydroxyanthraquinone-2-carboxylic acid) is mainly distributed in Polygonaceae plants, such as rhubarb palmatum, rhubarb tangut, Polygonum multiflorum, Polygonum cuspidatum, etc. One of the main active ingredients isolated and purified from a variety of traditional Chinese medicines. It has various pharmacological activities such as anti-inflammatory, anti-tumor, anti-bacterial, anti-viral, and anti-Alzheimer's disease. to be further developed

Method used

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  • Rhein derivative and antiviral application thereof
  • Rhein derivative and antiviral application thereof
  • Rhein derivative and antiviral application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104] Embodiment 1 (compound 1) 1, the preparation of 8-dihydroxy-3-(piperazine-1-carbonyl) anthracene-9,10-dione

[0105]

[0106]Rhein (200mg, 0.70mmol), triethylamine (142mg, 1.4mmol) and anhydrous piperazine (60mg, 0.70mmol) were added to N,N-dimethylformamide (5mL), and 2 -(7-benzotriazole oxide)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU) (266mg, 0.7mmol), react at room temperature for 1 hour. The reaction was quenched with water, then extracted 3 to 5 times with ethyl acetate, the organic phases were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, filtered, spin-dried, column chromatography (eluent: 50%-100% Ethyl acetate: petroleum ether) to isolate the product (180 mg, 73%).

[0107] 1 HNMR (400MHz, DMSO-d 6 )δ: 11.89 (s, 2H), 7.85 (t, J=8.0Hz, 1H), 7.73-7.67 (m, 2H), 7.43-7.41 (m, 2H), 3.67-3.19 (m, 8H).

Embodiment 2

[0108] Embodiment 2 (compound 2) 1, the preparation of 8-dihydroxy-3-(4-methylpiperazine-1-carbonyl) anthracene-9,10-dione

[0109]

[0110] The synthesis method is as in Example 1, replacing "anhydrous piperazine" with "N-methylpiperazine".

[0111] 1 HNMR (400MHz, DMSO-d 6 )δ: 11.91 (s, 2H), 7.86 (t, J=8.0Hz, 1H), 7.75-7.72 (m, 2H), 7.46-7.41 (m, 2H), 3.63-3.17 (m, 8H), 2.72 (s, 3H).

Embodiment 3

[0112] Embodiment 3 (compound 3) 1, the preparation of 8-dihydroxy-3-(4-ethylpiperazine-1-carbonyl) anthracene-9,10-dione

[0113]

[0114] The synthesis method is as in Example 1, replacing "anhydrous piperazine" with "N-ethylpiperazine".

[0115] 1 HNMR (400MHz, DMSO-d 6 )δ: 12.03(s, 1H), 11.92(s, 1H), 7.86(t, J=8.0Hz, 1H), 7.78-7.71(m, 2H), 7.50-7.41(m, 2H), 4.58(m , 2H), 3.70-3.17(m, 8H), 1.26 (t, J=8.0Hz, 3H).

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Abstract

The invention relates to a rhein derivative and an antiviral application thereof, and belong to a new drug development technology. The rhein derivative has a structure as shown in a general formula (I) or a formula (II), and experimental data show that the rhein derivative has better antiviral drug activity.

Description

[0001] cross reference [0002] The present invention claims the Chinese invention application with the application number 201911232603.3 submitted on December 5, 2019, and the Chinese invention application with the application number 202010025146.7 submitted on January 10, 2020 as the priority, the entire contents of which are deemed to be incorporated by reference this invention. technical field [0003] The invention relates to new drug development technology, in particular to a class of rhein derivative compounds and their antiviral application. Background technique [0004] Viral diseases are the most common infectious diseases that seriously threaten human health, with the characteristics of high infection and high variation. Most of the existing antiviral drugs are viral enzyme inhibitors, which have the advantages of clear targets, high specificity, and strong curative effect. However, the discovery of drug-resistant viruses and the continuous emergence of new viru...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/185C07D241/04C07C235/66C07D211/58C07D213/75C07D215/42C07D487/04C07D215/40A61K31/165A61K31/40A61K31/52A61K31/519A61K31/438A61K31/4409A61P31/12
CPCC07D295/185C07D241/04C07C235/66C07D211/58C07D213/75C07D215/42C07D487/04C07D215/40A61P31/12A61K31/165A61K31/40A61K31/438A61K31/4409A61K31/519A61K31/52A61K31/166A61K31/167A61K31/495A61K31/5375A61P31/20A61P31/22A61P31/14A61P31/16A61P31/18C07C235/84C07D211/22C07D211/16C07D213/16C07D235/02C07D239/70C07D295/13C07D295/192
Inventor 朱水芳田志清丛浩龙胡佳龙姜帆
Owner CHINA INSPECTION SCI PHARM BEIJING GRP CO LTD
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