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Coumarin-containing chalcone derivative, and preparation method and application thereof

A technology for chalcones and derivatives, which is applied to the application field of inhibiting plant bacteria, can solve problems such as no combination of coumarin and chalcone, and achieves high yield, mild reaction conditions, and good inhibitory activity. Effect

Active Publication Date: 2019-02-01
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In summary, there have been many research reports on the inhibition of bacteria by chalcones and coumarins, and the combination of the two has been studied in the inhibition of animal bacteria, but there is no research on the combination of coumarins and coumarins. Chalcone binding, and research reports on the inhibition of plant bacteria

Method used

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  • Coumarin-containing chalcone derivative, and preparation method and application thereof
  • Coumarin-containing chalcone derivative, and preparation method and application thereof
  • Coumarin-containing chalcone derivative, and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0029] The synthesis of 1-(4-(4-coumarinyl)-phenyl)-3-(2-pyridyl)-2-propen-1-one (the compound number is C1) comprises the following steps:

[0030] (1) Synthesis of 1-(4-hydroxyphenyl)-3-(2-pyridyl)-2-propen-1-one: p-hydroxyacetophenone (0.5g) and 2-pyridinecarbaldehyde (0.4mL ) into 30mL of ethanol, after stirring for about 15min, after stirring the system at room temperature for about 30min, add about 4mL of 4mol·L -1 NaOH solution, after the dropwise addition, remove the ice bath, and stir at room temperature for about 24h. After the reaction is over, transfer the system to a 1000mL beaker and add an appropriate amount of ice water, then use 5% dilute hydrochloric acid solution to adjust the pH of the system to about 5-6, a large amount of yellow solids precipitate, extract the solids, and finally use ethanol / water system (1:3) was recrystallized to obtain a yellow solid with a yield of 88%.

[0031] (2) Synthesis of 4-chlorocoumarin: put 4-hydroxycoumarin (4g) and phos...

Embodiment 2

[0034] The synthesis of 1-(4-(4-coumarinyl)-phenyl)-3-(4-chlorophenyl)-2-propen-1-one (the compound number is C2) comprises the following steps:

[0035] (1) Synthesis of 1-(4-hydroxyphenyl)-3-(4-chlorophenyl)-2-propen-1-one: as in the first (1) step of Example 1, the difference is that 4-chlorobenzene formaldehyde as raw material.

[0036] (2) Synthesis of 4-chlorocoumarin: as in step (2) of Example 1.

[0037] (3) Synthesis of 1-(4-(4-coumarinyl)-phenyl)-3-(4-chlorophenyl)-2-propen-1-one: as in Example 1 (3) step , the difference is that 1-(4-hydroxyphenyl)-3-(4-chlorophenyl)-2-propen-1-one is used as raw material.

Embodiment 3

[0039] The synthesis of 1-(4-(4-coumarinyl)-phenyl)-3-(2-thienyl)-2-propen-1-one (the compound number is C3) comprises the following steps:

[0040](1) Synthesis of 1-(4-hydroxyphenyl)-3-(2-thienyl)-2-propene-1-one: as in the first (1) step of Example 1, the difference is that thiophene-2-formaldehyde For the raw material.

[0041] (2) Synthesis of 4-chlorocoumarin: as in step (2) of Example 1.

[0042] (3) Synthesis of 1-(4-(4-coumarinyl)-phenyl)-3-(2-thienyl)-2-propene-1-one: as in step (3) of Example 1, The difference is that 1-(4-hydroxyphenyl)-3-(2-thienyl)-2-propen-1-one is used as raw material.

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Abstract

The invention discloses a coumarin-containing chalcone derivative, and a preparation method and an application thereof. The general formula of the derivative is represented by formula (1) shown in thedescription; and in the formula (I), R is a phenyl group, a substituted phenyl group, an aromatic heterocyclic group or a substituted aromatic heterocyclic group, wherein the R being the substitutedphenyl group is a phenyl group substituted with a methyl group, one or more methoxy groups, a trifluoromethyl group, a trifluoromethoxy group or one or more halogen atoms; and the R being the substituted aromatic heterocyclic group is a pyridyl group, a thienyl group, a furyl group or a substituted thiazolyl group. The coumarin-containing chalcone derivative has good inhibitory activity against rice bacterial blight and citrus canker, and the preparation method has the advantages of easily available raw materials, proceeding of a reaction at a low temperature, mild reaction conditions, simplicity in post-treatment, and high yield.

Description

technical field [0001] The present invention relates to the technical field of chemical engineering, in particular to a coumarin-containing chalcone derivative, a preparation method of the coumarin-containing chalcone derivative, and the coumarin-containing chalcone derivative Application of ketone derivatives in inhibiting plant bacteria. Background technique [0002] Chalcone is a natural organic compound. Chalcone and its derivatives are widely used in agriculture because of their good bactericidal, antiviral, insecticidal and other biological activities. [0003] In 2011, Liu Xiaofang et al. (Eur.J.Med.Chem, 2011,46,3469-3473.) reported a series of chalcones containing benzoic acid and 2,4-thiazolidinedione moieties, and carried out Antibacterial activity test, the results show that some compounds have good inhibitory activity against Gram-negative bacteria, and the minimum inhibitory concentration MIC value is 0.5-4mg / mL. [0004] In 2014, Yin et al. (Eur.J.Med.Chem, ...

Claims

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Application Information

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IPC IPC(8): C07D311/46C07D405/12C07D409/12C07D417/12C07D407/12A01N43/78A01N43/40A01N43/16A01P1/00
CPCA01N43/16A01N43/40A01N43/78C07D311/46C07D405/12C07D407/12C07D409/12C07D417/12
Inventor 薛伟王一会蒋仕春陈英郭涛夏榕娇汤旭贺鸣李娟金梅梅
Owner GUIZHOU UNIV
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