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

Myricetin derivative containing thiadiazole thioether structure and preparation method thereof

A technology of thiadiazole sulfide and derivatives, which is applied to the application of inhibiting plant viruses, and the field of preparation of thiadiazole sulfide-based myricetin derivatives, which can solve the problem that myricetin does not involve plant viruses, myricetin and its derivatives. Problems such as less research on derivatives

Active Publication Date: 2017-05-17
GUIZHOU UNIV
View PDF3 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the research on myricetin and its derivatives in pesticides is less, and the research on myricetin does not involve the research on plant viruses

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
  • Myricetin derivative containing thiadiazole thioether structure and preparation method thereof
  • Myricetin derivative containing thiadiazole thioether structure and preparation method thereof
  • Myricetin derivative containing thiadiazole thioether structure and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1, 3-((5-mercapto-1,3,4-thiadiazol-2-yl)methoxy)-5,7-dimethoxy-2-(3,4,5-trimethyl Oxyphenyl)-4H-chromen-4-one (compound number is III 1 ).

[0046] The first step: the preparation of 3-hydroxy-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one (intermediate A);

[0047] In a 100mL round bottom flask, add 1.86g (4mmol) myricetin and dissolve it in 50mL DMF, add 8.86g (64mmol) K 2 CO 3 After stirring for 50min, slowly add 3mL (48mmol) methyl iodide, after completion, raise the temperature to 40°C, and stir at this temperature for 48h, filter the precipitate from the reaction system, wash with dichloromethane, combine the filtrate, pour the filtrate into 100mL water , extracted with dichloromethane (3×30mL), combined the organic phases, concentrated under reduced pressure, diluted the concentrate with 30mL of absolute ethanol, raised the temperature to reflux for 1h, after the solution was clarified, added 8mL of concentrated hydrochloric acid under reflu...

Embodiment 2

[0054] Example 2, 5,7-dimethoxy-3-((5-(methylthio)-1,3,4-thiadiazol-2-yl)methoxy)-2-(3,4 ,5-trimethoxyphenyl)-4H-chromen-4-one (compound number is III 2 ).

[0055] Intermediate D was obtained by the steps of Example 1. In a 50mL round-bottomed flask, add intermediate D (0.97mmol), anhydrous potassium carbonate (1.45mmol), and 30mL acetonitrile in sequence, stir at room temperature for 0.5h, and slowly add a solution of iodomethane (1.45mmol) in acetonitrile (10mL) dropwise , be warmed up to 45°C, continue to react at this temperature for 4-6h, follow the reaction by TLC (reaction system shows fluorescence under ultraviolet light, developer: dichloromethane:methanol=7:1, V / V), stop the reaction, After cooling to room temperature, a large amount of solids were precipitated, left to stand, filtered, and recrystallized from methanol to obtain the target compound with a yield of 52.2% and a melting point of 165.0-166.0°C.

Embodiment 3

[0056] Example 3, 5,7-dimethoxy-3-((5-((3-methylbenzyl)thio)-1,3,4-thiadiazol-2-yl)methoxy) -2-(3,4,5-trimethoxyphenyl)-4H-chromene-4-one (compound number is III 3 ).

[0057] Synthesized according to the conditions and methods of Example 2 to obtain 5,7-dimethoxy-3-((5-((3-methylbenzyl)thio)-1,3,4-thiadiazole-2 -yl)methoxy)-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one, yield 46.2%, melting point 105.0-106.0°C.

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

PropertyMeasurementUnit
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
Login to View More

Abstract

The invention discloses a myricetin derivative containing a thiadiazole thioether structure. The myricetin derivative is shown as a general formula in the specification, wherein R is H, alkyl, benzyl, 4-(pyridyl)methylene, 3-(pyridyl)methylene, 2-(pyridyl) methylene, 5-(2-chloropyridine)methylene, 5-(2-chlorothiazole)methylene or ortho-, meta- and para- mono-substituted or poly-substituted methoxyacetic benzyl, nitrobenzyl, methylbenzyl and halogen atom benzyl. The myricetin derivative containing the thiadiazole thioether structure has high virus resistance, and can be used as a medicament for restraining plant viruses.

Description

technical field [0001] The invention relates to the technical field of chemical engineering, in particular to a preparation method of a thiadiazole sulfide myricetin derivative and its application in inhibiting plant viruses. Background technique [0002] Tobacco mosaic disease has the characteristics of high incidence and difficult control in crops, and is listed as one of the most destructive plant viruses. However, all the plant antiviral agents that have been commercialized so far have only 30-50% therapeutic activity against plant viruses at a concentration of 500 μg / mL, and the inhibition results are obviously unsatisfactory. Therefore, how to develop new, efficient and environmentally friendly plant antiviral agents is still an important challenge for drug creators. [0003] Myricetin belongs to the flavonoid alcohol compounds in natural products, which are widely distributed in nature. It has biological activities such as antibacterial, antiviral, antitumor, and ant...

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): C07D417/12C07D417/14A01P1/00
CPCC07D417/12C07D417/14
Inventor 薛伟钟新敏李普张橙王一会陈丽娟李琴阮祥辉张菊平赵珊桂婷张清
Owner GUIZHOU UNIV
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