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Chalcone derivative containing sulfonyl piperazine as well as preparation method and application thereof

A technology for chalcone derivatives and sulfonylpiperazine, which is applied in the field of chalcone derivatives containing sulfonylpiperazine and its preparation, can solve problems such as unreported, and achieve the effect of inhibiting the activity of plant bacteria and fungi

Active Publication Date: 2022-02-25
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, chalcone derivatives containing sulfonylpiperazine and their applications in pesticides have not been reported. Mango bacterial angular leaf spot 5 kinds of plant bacteria and their effects on rice sheath blight, cabbage black spot, strawberry moniliforme, cucumber wilt, capsicum anthracnose, litchi downy mildew, wheat scab, tobacco black stem The activity tests of 10 kinds of plant fungi including pathogen, mango anthracnose and tomato cinerea have not been reported

Method used

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  • Chalcone derivative containing sulfonyl piperazine as well as preparation method and application thereof
  • Chalcone derivative containing sulfonyl piperazine as well as preparation method and application thereof
  • Chalcone derivative containing sulfonyl piperazine as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Step 1, the preparation of 3-(2-chlorophenyl)-1-(4-hydroxyphenyl)-2-propen-1-one (intermediate 1):

[0040] Add 1.5g p-hydroxyacetophenone (11.02mmol) and 1.86g 2-chlorobenzaldehyde (13.22mmol) in a 100mL three-necked flask, then add 25mL (30.05mmol) ethanol to fully dissolve the reactant, then add 35mL 5% of NaOH (30.05 mmol) solution. Magnetic stirring, under ice bath conditions for 12 hours until the reactant reacts completely, monitor with TLC until the raw material point disappears, pour the reaction system in the three-necked flask into a 500mL ice bath beaker, add 5% HCl drop by drop with a rubber dropper solution, until the pH value in the beaker was measured to be about 6 with pH test paper, a large amount of white solids were precipitated at the bottom of the beaker as intermediate 1, filtered by suction, and dried in a far-infrared drying oven (TIR-X31 type ) 8h (8-48h can be), standby, yield: 92%.

[0041] Step 2, the preparation of 1-((4-chlorophenyl)sulf...

Embodiment 2

[0048] Step 1, the preparation of 1-(4-hydroxyphenyl)-3-(pyridin-2-yl)-2-propen-1-one (intermediate 1):

[0049] Same as step 1 of Example 1, the only difference is that 2-chlorobenzaldehyde is replaced by 2-pyridinecarbaldehyde in an equimolar amount.

[0050] Step 2, the preparation of 1-((4-chlorophenyl)sulfonyl)piperazine (intermediate 2):

[0051] Same as Step 2 of Example 1.

[0052] Step 3, preparation of 2-chloro-1-(4-((4-chlorophenyl)sulfonyl)piperazin-1-yl)ethan-1-one (intermediate 3):

[0053] Same as Step 3 of Example 1.

[0054] Step 4, 1-(4-(2-(4-((4-chlorophenyl)sulfonyl)piperazin-1-yl)-2-oxoethoxy)phenyl)-3-(pyridine- Preparation of 2-yl) prop-2-en-1-one (target compound Z2):

[0055] Same as step 4 of Example 1, the only difference is that 3-(2-chlorophenyl)-1-(4-hydroxyphenyl)-2-propen-1-one is replaced by an equimolar amount of 1-(4 -Hydroxyphenyl)-3-(pyridin-2-yl)-2-propen-1-one. Yield: 69%.

Embodiment 3

[0057] Step 1, the preparation of 1-(4-hydroxyphenyl)-3-(pyridin-4-yl)-2-propen-1-one (intermediate 1):

[0058] Same as step 1 of Example 1, the only difference is that 2-chlorobenzaldehyde is replaced by 4-pyridinecarbaldehyde in an equimolar amount.

[0059] Step 2, the preparation of 1-((4-chlorophenyl)sulfonyl)piperazine (intermediate 2):

[0060] Same as Step 2 of Example 1.

[0061] Step 3, preparation of 2-chloro-1-(4-((4-chlorophenyl)sulfonyl)piperazin-1-yl)ethan-1-one (intermediate 3):

[0062] Same as Step 3 of Example 1.

[0063] Step 4, 1-(4-(2-(4-((4-chlorophenyl)sulfonyl)piperazin-1-yl)-2-oxoethoxy)phenyl)-3-(pyridine- Preparation of 4-yl) prop-2-en-1-one (target compound Z3):

[0064] Same as step 4 of Example 1, the only difference is that 3-(2-chlorophenyl)-1-(4-hydroxyphenyl)-2-propen-1-one is replaced by an equimolar amount of 1-(4 -Hydroxyphenyl)-3-(pyridin-4-yl)-2-propen-1-one. Yield: 72%.

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Abstract

The invention discloses a chalcone derivative containing sulfonyl piperazine as well as a preparation method and application thereof, and relates to the technical field of compound synthesis. The preparation method comprises the following steps of: reacting p-hydroxyacetophenone with substituted aromatic aldehyde under an alkaline condition to obtain an intermediate 1; reacting substituted benzene sulfonyl chloride with piperazine in an organic solvent A to obtain an intermediate 2; reacting the intermediate 2 with chloroacetyl chloride in an organic solvent A to obtain an intermediate 3; and carrying out a base catalysis reaction on the intermediate 1 and the intermediate 3 in an organic solvent B to obtain the chalcone derivative containing sulfonyl piperazine. The chalcone derivative containing sulfonyl piperazine disclosed by the invention has excellent activity of inhibiting plant bacteria and fungi, and can be used for preparing agents for inhibiting plant bacteria.

Description

technical field [0001] The invention relates to the technical field of compound synthesis, in particular to a chalcone derivative containing sulfonylpiperazine and a preparation method and application thereof. Background technique [0002] Flavonoids and isoflavones are an important class of natural products widely found in edible plants. As the core skeleton unit of flavones and isoflavones, chalcones widely exist in natural products. Such compounds have a wide range of biological activities, such as antibacterial, anticancer, anti-inflammatory, anti-malarial and so on. Due to the α,β-unsaturated carbonyl in the structure of chalcone, it can carry out conjugate addition with the nucleophilic group in the bacteria and cause the death of the bacteria. At the same time, due to the good flexibility of the chalcone structural unit, chalcone as a substrate can be combined with various active groups. Therefore, these compounds have high utilization value. [0003] In 2017, Don...

Claims

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Application Information

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IPC IPC(8): C07D295/26A01N43/60A01P3/00A01P1/00
CPCC07D295/26A01N43/60Y02A50/30
Inventor 薛伟周清陈帅詹文亮胡蝶孙楠周然周远香袁春梅龚晨裕幸丽毛飘张桃张念何帮灿田姣刘燚
Owner GUIZHOU UNIV
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