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

Quinoxaline-containing 1,4-pentadiene-3-one derivatives, and preparation method and application thereof

A technology of pentadiene and quinoxaline, applied in the field of antiviral activity and the preparation of 1,4-pentadien-3-one derivatives, to achieve high therapeutic and high anti-plant virus activity

Inactive Publication Date: 2018-01-19
GUIZHOU UNIV
View PDF0 Cites 13 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] At present, there are no relevant reports on introducing quinoxaline into the pentadiene structure and testing the anti-plant virus 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
  • Quinoxaline-containing 1,4-pentadiene-3-one derivatives, and preparation method and application thereof
  • Quinoxaline-containing 1,4-pentadiene-3-one derivatives, and preparation method and application thereof
  • Quinoxaline-containing 1,4-pentadiene-3-one derivatives, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The synthesis of 1-(4-(2-quinoxalinyl)phenyl)-5-(2-thienyl)-1,4-pentadien-3-one (the compound number is A1) comprises the following steps:

[0041] (1) Synthesis of 4-(hydroxyphenyl)-3-buten-2-one: 4-hydroxybenzaldehyde (6.1g) was added to 60mL of acetone, after stirring for about 15min, the reaction system was ice-bathed for about After 30 min, add about 100 mL of 5% NaOH solution to the system, after the dropwise addition is complete, remove the ice bath, and stir at room temperature for about 24 h. After the reaction is over, transfer the system to a 500mL beaker and add an appropriate amount of ice water, and then use 5% dilute hydrochloric acid solution to adjust the pH of the system to about 5-6. After a large amount of yellow solids precipitate, extract the solids, and finally use ethanol to / water system recrystallized to obtain a yellow solid with a yield of 68%.

[0042] (2) Synthesis of 1-(2-thienyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one: 4-(hydroxyphenyl)...

Embodiment 2

[0046] The synthesis of 1-(4-(2-quinoxalinyl)phenyl)-5-(4-methylphenyl)-1,4-pentadien-3-one (compound number is A2), including the following step:

[0047] (1) Synthesis of 4-(hydroxyphenyl)-3-buten-2-one: as in step (1) of Example 1.

[0048] (2) Synthesis of 1-(4-methylphenyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one: as in step (2) of Example 1, the difference is With 4-methylbenzaldehyde as raw material.

[0049] (3) Synthesis of 2-chloroquinoxaline: as in step (3) of Example 1.

[0050] (4) Synthesis of 1-(4-(2-quinoxalinyl)phenyl)-5-(4-methylphenyl)-1,4-pentadien-3-one: as in Example 1 (4) step, the difference is that 1-(4-methylphenyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one is used as raw material.

Embodiment 3

[0052] The synthesis of 1-(4-(2-quinoxalinyl)phenyl)-5-(3-pyridyl)-1,4-pentadien-3-one (the compound number is A3) comprises the following steps:

[0053] (1) Synthesis of 4-(hydroxyphenyl)-3-buten-2-one: as in step (1) of Example 1.

[0054] (2) Synthesis of 1-(3-pyridyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one: as in step (2) of Example 1, the difference is that pyridine -3-formaldehyde as raw material.

[0055] (3) Synthesis of 2-chloroquinoxaline: as in step (3) of Example 1.

[0056] (4) Synthesis of 1-(4-(2-quinoxalinyl) phenyl)-5-(3-pyridyl)-1,4-pentadien-3-one: as in Example 1 (4 ) step, the difference is that 1-(3-pyridyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one is used as raw material.

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 quinoxaline-containing 1,4-pentadiene-3-one derivatives. The quinoxaline-containing 1,4-pentadiene-3-one derivatives are characterized by having a general formula which is as shown in the specification, wherein R1 is a phenyl, a substituted phenyl or a substituted aromatic heterocycle, and R2 one or more hydrogen atoms, methoxyls, nitryls, methyls, trifluoromethyls or halogen atoms contained on the 5-position, 6-position, 7-position and the 8-position of a quinoxaline structure. The compound provided by the invention has very good treating, protecting and passivating effects on TMV (Tobacco Mosaic Virus), shows high resistance to plant virus, and can be used for preparing a plant virus resisting pesticide.

Description

technical field [0001] The invention relates to the technical field of chemical industry, in particular to a preparation method of quinoxaline-containing 1,4-pentadien-3-one derivatives and its application in antiviral activity. Background technique [0002] Natural products and their biomimetic pesticides are environmentally friendly, have unique action sites and high selectivity, and play an increasingly important role in the control of plant diseases. Curcumin, a polyphenolic compound derived from turmeric, is widely used as a spice, food preservative, monosodium glutamate, and dye. 1,4-pentadienone compound, as an important curcumin derivative, has broad-spectrum biological activities such as insecticidal, antibacterial, anti-plant virus, anti-cancer, anti-inflammatory and anti-oxidative, It has gradually become one of the hot spots in the field of pharmaceutical creation. In particular, related reports in recent years have shown that 1,4-pentadien-3-ones have extremel...

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): C07D401/14C07D401/12C07D405/12C07D239/88C07D241/44A01N43/54A01N43/60A01P1/00
CPCA01N43/60C07D241/44C07D401/12C07D405/12C07D409/12
Inventor 薛伟李琴张橙李普王一会陈丽娟吴小琼贺鸣王俊
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