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

Thiourea compounds and preparation method and application thereof

A compound, thiourea technology, applied in the field of biomedicine

Inactive Publication Date: 2019-07-05
MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
View PDF7 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

One group of thiourea compounds described in the present invention has no domestic and foreign related literature reports

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
  • Thiourea compounds and preparation method and application thereof
  • Thiourea compounds and preparation method and application thereof
  • Thiourea compounds and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] , the synthesis of 1-(4-hydroxyl-benzyl)-3-(3-methoxy-4-oxazol-5-yl-phenyl)-thiourea (1)

[0058] In a 25ml flask, the compound 3-methoxy-4-(oxazol-5-yl)aniline (1.0mmol) and 1,1'-thiocarbonyldiimidazole (TCDI, 1.1mmol) were dissolved in anhydrous tetrahydrofuran (THF, 4.0 mL) was stirred at room temperature for 2 hours, 4-hydroxy-benzylamine (2.0 mmol) was added and then 4-dimethylaminopyridine (DMAP, 0.1 mmol) was added to the solution. The mixture was further stirred overnight at reflux temperature. The solvent was removed under reduced pressure. Extracted with ethyl acetate (3 x 20 mL), the organic layer was separated, washed with saturated aqueous potassium bisulfate solution and water, then dried over anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified by flash chromatography on silica gel, eluting with a gradient of 30-60% ethyl acetate in petroleum ether, to afford compound 1. Pale yellow solid, yield 35%. 1 H-NMR (500MHz...

Embodiment 2

[0059] , the synthesis of 1-(4-methoxy-benzyl)-3-(3-methoxy-4-oxazol-5-yl-phenyl)-thiourea (2)

[0060] Using 3-methoxy-4-(oxazol-5-yl)aniline and 4-methoxy-benzyl as starting materials, compound 2 was obtained according to the similar method of Example 1. White solid, yield 37%. 1 H-NMR (500MHz, DMSO-d 6 )δ (ppm): 10.15 (1H, s), 8.55 (1H, s), 8.40 (1H, s), 7.62 (1H, d, J = 8.5Hz), 7.59 (1H, d, J = 1.0Hz) ,7.46(1H,s),7.30(2H,d,J=8.5Hz),7.13(1H,dd,J 1 =8.5Hz,J 2 =1.0Hz), 6.91(2H,d,J=8.5Hz), 4.68(2H,s), 3.89(3H,s), 3.74(3H,s).

Embodiment 3

[0061] , 1-(3,4-dimethoxy-benzyl)-3-(3-methoxy-4-oxazol-5-yl-phenyl)-thiourea (3) synthesis

[0062] Using 3-methoxy-4-(oxazol-5-yl)aniline and 3,4-dimethoxy-benzylamine as raw materials, according to the similar method of Example 1, compound 3 was obtained. White solid, yield 37%. 1 H-NMR (500MHz, DMSO-d 6 )δ (ppm): 9.82 (1H, s), 8.40 (1H, s), 8.29 (1H, s), 7.63 (1H, d, J = 8.5Hz), 7.50 (1H, s), 7.47 (1H, s),7.10(1H,d,J=8.5Hz),7.02(1H,s),6.93(1H,d,J=8.5Hz),6.90(1H,d,J=8.5Hz),4.66(2H, s), 3.89(3H,s), 3.76(3H,s), 3.74(3H,s).

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 group of thiourea compounds and a preparation method and application thereof. The oxazole phenylthiourea compound or a pharmaceutically acceptable salt thereof has a structure represented by the general formula (I). According to the present inventors, a class of compounds having both IMPDH inhibitory activity and broad-spectrum antiviral activity and pharmaceutical saltsthereof are screened and obtained by studying the structure-activity relationship and the action mechanism of active compounds, wherein the virus comprises influenza virus, hepatitis B virus, coxsackie virus and herpes simplex virus. The invention lays a foundation for the development and application of the compounds as antiviral and other related drugs and pharmaceutical compositions thereof, andprovides a new technical means for antiviral treatment.

Description

technical field [0001] The invention relates to a group of oxazole phenylthiourea compounds, a preparation method of the compounds and their IMPDH inhibitory activity and antiviral activity. The invention belongs to the field of biomedicine. Background technique [0002] Viral infections pose a threat to every living organism in all domains of life. At present, the antiviral drugs used clinically all target viral proteins, and the mechanism of action is to inhibit the replication of the virus or block the invasion of the virus. Viruses rely on continuous mutation to escape drug attacks. Drugs targeting viral proteins all cause virus mutation and drug resistance, which has become a worldwide problem. Influenza is an infectious disease caused by various types of influenza viruses and is characterized by a highly contagious acute respiratory syndrome. Seasonal influenza outbreaks occur around the world each year, causing approximately 3 to 5 million cases of severe illness a...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/32C07D413/12A61K31/421A61K31/422A61P31/20A61P31/14A61P31/16A61P31/22A61P31/12
CPCA61P31/12A61P31/14A61P31/16A61P31/20A61P31/22C07D263/32C07D413/12
Inventor 仲兆金邢国凌李卓荣李玉环郑智慧左利民张大军高荣梅
Owner MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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