Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

1,8-dihydroxyl-9,10-anthraquinone derivative and preparation method and application thereof

A technology of anthraquinone derivatives and dihydroxyl, which is applied in 1 field, can solve the problems of general strength of action and increased activity, and achieve good anti-HCV activity effect

Active Publication Date: 2019-05-14
SHANGHAI INST OF PHARMA IND +1
View PDF3 Cites 2 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 1,8-dihydroxyl-9,10-anthraquinone derivative and preparation method and application thereof
  • 1,8-dihydroxyl-9,10-anthraquinone derivative and preparation method and application thereof
  • 1,8-dihydroxyl-9,10-anthraquinone derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Dissolve 5mmol emodin in 15mL tetrahydrofuran, add 10mmol triethylamine and 10mmol p-toluenesulfonyl chloride, react at room temperature for 5 hours, distill off the solvent under reduced pressure, add 15mL water, then extract three times with 15mL ethyl acetate, combine the organic phases, 15mL After washing once with water, compound 1 was obtained by column chromatography (PE / EA=4 / 1), with a yield of 59%.

[0042] 1 H NMR (500MHz, CDCl 3 )δ12.17(s, 1H), 11.88(s, 1H), 7.79(d, J=6.5Hz, 2H), 7.63(s, 1H), 7.44(s, 1H), 7.36(d, J=6.5 Hz, 2H), 7.11(s, 1H), 7.00(s, 1H), 2.46(s, 6H, overlapped); 13 C NMR (126MHz, CDCl 3 )δ191.5, 180.7, 163.88, 162.9, 155.5, 149.7, 146.2, 135.3, 132.8, 132.1, 130.1, 128.4, 124.7, 121.7, 117.0, 114.7, 113.8, 113.4, 22.2, 21.7; ESI-MS: 422.9[M-H] - .

Embodiment 2

[0044] Dissolve 5mmol emodin in 15mL acetone, add 10mmol potassium carbonate and 15mmol methyl chloroformate, heat up to 45°C for 12 hours, distill off the solvent under reduced pressure, add 15mL water, then extract three times with 15mL ethyl acetate, and combine the organic phases , washed once with 15 mL of water, and column chromatography (PE / EA=4 / 1) gave Compound 1 with a yield of 65%.

[0045] 1 H NMR (500MHz, CDCl 3 )δ12.21(s, 1H), 11.95(s, 1H), 7.66(s, 1H), 7.64(d, J=2.5Hz, 1H), 7.15(d, J=2.0Hz, 1H), 7.18( d, J=1.0Hz, 1H), 3.96(s, 3H), 2.47(s, 3H); 13 CNMR (126MHz, CDCl 3 )δ191.5, 181.1, 164.1, 162.8, 157.1, 152.8, 149.4, 135.2, 133.0, 124.7, 121.7, 115.9, 114.0, 113.5, 113.2, 55.9, 22.2; ESI-MS: m / z 329.2 [M+H] + ;351.1[M+Na] + ;326.9[M-H] - .

Embodiment 3

[0047] Dissolve 5mmol of emodin in 15mL of acetone, add 10mmol of potassium carbonate and 15mmol of 4-methoxybenzyl chloride, heat up to 45°C for 12 hours, distill off the solvent under reduced pressure, add 15mL of water, and extract three times with 15mL of ethyl acetate. The organic phases were combined, washed once with 15 mL of water, and subjected to column chromatography (PE / EA=4 / 1) to obtain Compound 1 with a yield of 53%.

[0048] 1 H NMR (500MHz, CDCl 3 )δ12.29(s, 1H), 12.11(s, 1H), 7.62(s, 1H), 7.44(d, J=2.5Hz, 1H), 7.37(d, J=8.5Hz, 2H), 7.08( s, 1H), 6.94(d, J=8.5Hz, 2H), 6.75(d, J=2.5Hz, 1H), 5.12(s, 2H), 3.83(s, 3H), 2.45(s, 3H); 13 C NMR (126MHz, CDCl 3 )δ190.8, 182.0, 165.7, 165.1, 162.5, 159.8, 148.4, 135.2, 133.2, 129.4, 127.3, 124.5, 121.3, 120.0, 114.2, 113.7, 110.3, 108.8, 107.7, 10.2, 95.3 - MS: m / z 389.1 [M-H] - .

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a 1,8-dihydroxyl-9,10-anthraquinone derivative and a preparation method and application thereof and provides application of a 1,8-dihydroxyl-9,10-anthraquinone derivative shownin a formula I or a pharmaceutically acceptable salt of the 1,8-dihydroxyl-9,10-anthraquinone derivative to preparation of medicines for treatment and / or prevention of hepatitis C. The formula I is as shown in the specification, wherein R refers to C1-C6 alkoxy carbonyl, R<1> substituted or non-substituted benzenesulfonyl, or R<2> substituted or non-substituted benzyl, and R<1> and R<2> are C1-C4alkyl or C1-C4 alkoxy independently. The 1,8-dihydroxyl-9,10-anthraquinone derivative is high in anti-HCV activity.

Description

technical field [0001] The invention relates to a 1,8-dihydroxy-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. The anti-HCV positive rate of healthy people in my country 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 will...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C303/28C07C309/73C07C68/02C07C69/96C07C46/00C07C50/34A61K31/122A61K31/255A61K31/265A61P1/16A61P31/14
Inventor 孙青欧阳丹薇袁虎吴彤张卫东罗序凯李玉柱
Owner SHANGHAI INST OF PHARMA IND
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com