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2-aminomethyl-9,10-anthraquinone derivative, its preparation method and application

An anthraquinone derivative, amine methyl technology, applied in the preparation of organic compounds, chemical instruments and methods, pharmaceutical formulations, etc., can solve the problems of general action strength, increase activity, etc., and achieve the effect of good anti-HCV activity

Active Publication Date: 2021-09-03
SHANGHAI INST OF PHARMA IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Patent CN200810203112.1 also discloses that emodin methyl ether has a certain inhibitory effect on hepatitis C virus, but the strength of the effect is average, and further structural modification is required to increase the activity

Method used

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  • 2-aminomethyl-9,10-anthraquinone derivative, its preparation method and application
  • 2-aminomethyl-9,10-anthraquinone derivative, its preparation method and application
  • 2-aminomethyl-9,10-anthraquinone derivative, its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Dissolve 5mmol of emodin methyl ether in 15mL of dioxane, add 10mmol of formaldehyde aqueous solution, 40mmol of acetic acid and 10mmol of dimethylamine, heat up to 85°C for 12 hours, evaporate the solvent under reduced pressure, add 15mL of saturated sodium bicarbonate aqueous solution, and then Extracted three times with 15 mL of dichloromethane, combined the organic phases, washed once with 15 mL of water, and recrystallized from ethyl acetate to obtain compound 1 with a yield of 75%. 2-(Dimethylamino)methyl-1,8-dihydroxy-3methoxy-6-methylanthraquinone-9,10-dione, 2-((dimethylamino)methyl)-1,8- dihydroxy-3-methoxy-6-methylanthracene-9, 10-dione;

[0059] 1 H NMR (500MHz, CDCl 3 )δ12.28(s, 1H), 7.61(s, 1H), 7.41(s, 1H), 7.08(s, 1H), 4.02(s, 3H), 3.63(s, 2H), 2.45(s, 3H ), 2.34(s, 6H); 13 C NMR (126MHz, CDCl 3 )δ190.8, 182.3, 164.5, 163.2, 162.5, 148.2, 134.4, 133.0, 124.6, 121.0, 119.7, 113.8, 110.9, 102.8, 56.5, 50.4, 45.4, 22.1; ESI-MS: m / z 342.2 [M+ H] + . ...

Embodiment 2

[0061] The reaction conditions and operations were the same as in Example 1, except that dimethylamine was replaced by morpholine to obtain compound 2 with a yield of 69%.

[0062] 1 H NMR (500MHz, CDCl 3 )δ12.74(s, 1H), 12.11(s, 1H), 7.63(s, 1H), 7.24(s, 1H), 7.08(s, 1H), 3.99(s, 2H), 3.83(s, 3H ), 3.81(brs, 4H), 2.69(brs, 4H), 2.47(s, 3H); 13 CNMR (126MHz, CDCl 3 )δ190.9, 182.3, 166.6, 162.5, 162.1, 148.7, 134.9, 133.8, 124.9, 121.8, 120.5, 114.5, 112.9, 110.8, 108.9, 66.6, 55.9, 54.1, 53.4, 22.2; ESI-MS: m / z .2[M+H] + .

Embodiment 3

[0064] Dissolve 5 mmol emodin in 15 mL dioxane, add 10 mmol aqueous formaldehyde, 40 mmol acetic acid and 10 mmol 4-piperidinylpiperidine, heat up to 85°C for 12 hours, evaporate the solvent under reduced pressure, add 15 mL saturated sodium bicarbonate The aqueous solution was extracted three times with 15 mL of dichloromethane, the organic phases were combined, washed once with 15 mL of water, and recrystallized from ethyl acetate to obtain compound 3 with a yield of 41%.

[0065] 1 H NMR (500MHz, CDCl 3 )δ12.71(s, 1H), 12.13(s, 1H), 7.61(s, 1H), 7.14(s, 1H), 7.03(s, 1H), 3.97(s, 2H), 3.57-3.89(m , 8H), 2.64-2.91(m, 8H), 2.45(s, 3H), 1.75-1.85(m, 2H); 13 C NMR (126MHz, CDCl 3 )δ190.7, 181.5, 167.6, 163.5, 162.7, 147.9, 135.1, 133.2, 124.1, 121.1, 120.2, 115.1, 113.3, 111.2, 107.9, 71.1, 66.6, 57.9, 55.9, 52.1, 53.2, 25 ;ESI-MS: m / z 451.2 [M+H] + .

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Abstract

The invention discloses a 2-aminomethyl-9,10-anthraquinone derivative, its preparation method and application. The present invention provides an application of a 2-aminomethyl-9,10-anthraquinone derivative shown in formula I or a pharmaceutically acceptable salt thereof in the preparation of a drug for treating and / or preventing hepatitis C ; where R 1 and R 2 independently for R 4 substituted or unsubstituted C 1 ~C 6 Alkyl, or, R 1 , R 2 and the N atoms connected to them together form R 5 Substituted or unsubstituted "heteroatoms selected from one or more of N, O and S, 4-7 membered heterocycloalkyl groups with 1-3 heteroatoms". The 2-aminomethyl-9,10-anthraquinone derivatives provided by the invention show better anti-HCV activity.

Description

technical field [0001] The invention relates to a 2-aminomethyl-9,10-anthraquinone derivative, its preparation method and application. Background technique [0002] Hepatitis C is caused by hepatitis C virus (HCV) infection and is mainly transmitted by blood / body fluids. The World Health Organization estimates that 170 million people are infected with HCV worldwide. In my country, the anti-HCV positive rate of healthy people is 0.7% to 3.1%, about 38 million people. Due to various factors such as the biological characteristics of the virus and the immune function of the host, it is often difficult for the body’s immunity to effectively clear the virus, resulting in about 50% to 80% of HCV-infected patients developing chronic hepatitis, of which 20% to 30% will develop into liver cirrhosis. Every year, 1% to 4% of patients with liver cirrhosis develop hepatocellular carcinoma. Because HCV is transmitted through blood, it is chronic and occult. Some HCV-infected patients wi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C225/24C07C221/00C07D211/58C07D295/116A61K31/137A61K31/40A61K31/4453A61K31/4545A61K31/496A61K31/5377A61P31/14
Inventor 孙青䶮欧阳丹薇袁虎吴彤张卫东罗序凯李玉柱
Owner SHANGHAI INST OF PHARMA IND CO LTD
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