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Quinoxaline-containing chalcone derivative and preparation method and application thereof

A derivative, the technology of chalcone, which is applied in the field of inhibiting the activity of plant pathogens, can solve the problems that have not been seen, and achieve the effects of mild reaction conditions, high yield and simple post-treatment

Active Publication Date: 2019-05-31
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In summary, the compounds containing chalcone and quinoxaline have good biological activity, but there are no related reports about introducing quinoxaline into the chalcone structure to inhibit the activity of plant pathogens

Method used

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  • Quinoxaline-containing chalcone derivative and preparation method and application thereof
  • Quinoxaline-containing chalcone derivative and preparation method and application thereof
  • Quinoxaline-containing chalcone derivative and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0028] The synthesis of 1-(4-(2-quinoxalinyl) phenyl)-3-(4-methylphenyl) chalcone (the compound number is A1) comprises the following steps:

[0029] (1) Synthesis of 1-(4-hydroxyphenyl)-3-(p-tolyl)chalcone: 4-(hydroxyacetophenone (2g), p-tolualdehyde (2.12g) and 50mL ethanol Add it into a 250mL three-neck flask, stir for about 30min, add 12mL of 4mol / L NaOH solution to the system, after the dropwise addition is complete, stir in an ice bath for about 12h. After the reaction is completed, transfer the system to a 500mL beaker Add appropriate amount of ice water, and then adjust the pH of the system to about 5-6 with 5% dilute hydrochloric acid solution, a large amount of milky white solid is precipitated, and the solid is extracted to obtain milky white solid with a yield of 76%.

[0030] (2) Synthesis of 2-chloroquinoxaline: 2-hydroxyquinoxaline (2g) and phosphorus oxychloride (20mL) were placed in a 100mL there-necked flask and stirred, added 5 drops of DMF, and the system w...

Embodiment 2

[0033] The synthesis of 3-(pyridin-2-yl)-1-(4-(quinoxalin-2-yloxy)phenyl)chalcone (compound number is A2) comprises the following steps:

[0034] (1) Synthesis of 1-(4-hydroxyphenyl)-3-(pyridin-2-yl)chalcone: as in step (1) of Example 1, the difference is that pyridinecarbaldehyde is used as a raw material.

[0035] (2) Synthesis of 2-chloroquinoxaline: as in step (2) of Example 1.

[0036] (3) Synthesis of 3-(pyridin-2-yl)-1-(4-(quinoxalin-2-yloxy)phenyl)chalcone: as in step (3) of Example 1. The difference is that 1-(4-hydroxyphenyl)-3-(pyridin-2-yl)chalcone and 2-chloroquinoxaline are used as raw materials.

Embodiment 3

[0038] 1-(4-(quinoxalin-2-yloxy)phenyl)-3-(thiophen-2-yl)chalcone (the compound number is A3), comprising the following steps:

[0039](1) Synthesis of 1-(4-hydroxyphenyl)-3-(thiophen-2-yl)chalcone: as in step (1) of Example 1, the difference is that thiophenecarbaldehyde is used as a raw material.

[0040] (2) Synthesis of 2-chloroquinoxaline: as in step (2) of Example 1.

[0041] (3) Synthesis of 1-(4-(quinoxalin-2-yloxy)phenyl)-3-(thiophen-2-yl)chalcone: as in step (3) of Example 1. The difference is that 1-(4-hydroxyphenyl)-3-(thiophen-2-yl)chalcone and 2-chloroquinoxaline are used as raw materials.

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Abstract

The invention discloses a quinoxaline-containing chalcone derivative and a preparation method and application thereof. The general formula of the quinoxaline-containing chalcone derivative is shown inthe description, wherein X represents 2-O or 4-O, and R1 refers to a phenyl group, a heterocyclic group and one or more substituted phenyl groups with halogen at the 2nd-6th positions, C1-C6 alkyl atthe 2nd-6th positions, C1-C6 alkoxy at the 2nd-6th positions, nitro at the 2nd-6th positions, amino at the 2nd-6th positions and trifluoromethyl at the 2nd-6th positions; R2 represents one or more hydrogen atoms, C1-C6 alkoxy groups, nitro groups, C1-C6 alkyl groups and trifluoromethyl groups or halogen atoms at the 5th position, 6th position and 7th position or 8th position in a quinoxaline structure. The derivative can inhibit xanthomonas oryzae, xanthomonas citri and ralstonia solanacearum, raw materials are easily obtained, the reaction condition is mild, the post-treatment is simple, andthe yield is high.

Description

technical field [0001] The present invention relates to the field of chemical technology, in particular to a quinoxaline-containing chalcone derivative, a preparation method of the quinoxaline-containing chalcone derivative, and the quinoxaline-containing chalcone derivative. The application of chalcone derivatives in inhibiting the activity of plant pathogens. 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. Chalcone is a natural flavonoid compound that is commonly found in the roots and stems of medicinal plants such as licorice and safflower. Studies have found that chalcones and their derivatives have biological activities such as anti-cancer, anti-inflammatory, anti-oxidation, and antibacterial. In addition, they also have agricultural activities such as anti-virus and insecticide, so they h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/42C07D401/12C07D409/12C07D241/44A01P1/00
Inventor 薛伟夏榕娇郭涛贺军陈梅苏时军汤旭蒋仕春陈英贺鸣
Owner GUIZHOU UNIV
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