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Chalcone derivative containing thioether triazole, preparation method and application

A kind of derivative, the technology of chalcone is applied in the field of preparation of chalcone derivatives to achieve excellent effect of inhibiting plant pathogens

Active Publication Date: 2019-05-28
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, there are no relevant reports on the antibacterial activity of introducing thioether-containing triazoles into the chalcone structure

Method used

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  • Chalcone derivative containing thioether triazole, preparation method and application
  • Chalcone derivative containing thioether triazole, preparation method and application
  • Chalcone derivative containing thioether triazole, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 1-(4-(2-((4-Amino-5-methyl-4H-1,2,4-triazol-3-yl)thio)ethoxy)phenyl)-3-(thiophene- 2-yl)-2-propen-1-one (target compound B 1 ) preparation method, comprising the following steps:

[0029] (1) Preparation of hydrazinothiohydrazide (intermediate 1):

[0030] Add 20mL of 85% hydrazine hydrate and 60mL of water to a three-neck flask equipped with a thermometer, dropping funnel and condenser (the upper port is connected with a tail gas outlet pipe), and control the temperature at about 50°C. Under electromagnetic stirring, 6 mL of CS2 was added dropwise within 1 h, and then the mixed solution was refluxed at 90° C. for 1 h, cooled and crystallized, filtered with suction, and recrystallized in water to obtain colorless needle-shaped crystals (intermediate 1), yield: 82% .

[0031] (2) Preparation of 4-amino-5-methyl-4H-1,2,4-triazole-3-mercapto (intermediate 2):

[0032] Take 3.18g (0.03mol) of hydrazinothiohydrazide (intermediate 1) in a flask, add 10mL of glacial acetic...

Embodiment 2

[0040] 1-(2-(2-((4-Amino-5-methyl-4H-1,2,4-triazol-3-yl)thio)ethoxy)phenyl)-3-(thiophene- 2-yl)-2-propen-1-one (target compound B 2 ) preparation method, comprising the following steps:

[0041] (1) Preparation of hydrazinothiohydrazide (intermediate 1):

[0042] As in the first (1) step of Example 1.

[0043] (2) Preparation of 4-amino-5-methyl-4H-1,2,4-triazole-3-mercapto (intermediate 2):

[0044] As in embodiment 1 (2) step.

[0045] (3) Preparation of 1-(2-hydroxyphenyl)-3-(thiophen-2-yl)-2-propen-1-one (intermediate 3):

[0046] As in step (3) of Example 1, the difference is that X is 2-O.

[0047] (4) Preparation of 1-(thiophen-2-yl)-3-(4-(2-bromoethoxy)phenyl)-chalcone (intermediate 4):

[0048] As in step (4) of Example 1, the difference is that X is 2-O.

[0049] (5) 1-(2-(2-((4-amino-5-methyl-4H-1,2,4-triazol-3-yl)thio)ethoxy)phenyl)-3- (Thien-2-yl)-2-propen-1-one (target compound B 2 ) preparation:

[0050] As in step (5) of Example 1, the difference is t...

Embodiment 3

[0052] 1-(2-(2-((4-Amino-5-methyl-4H-1,2,4-triazol-3-yl)thio)ethoxy)phenyl)-3-(4- Nitro)-2-propen-1-one (target compound B 3 ) preparation method, comprising the following steps:

[0053] (1) Preparation of hydrazinothiohydrazide (intermediate 1):

[0054] As in the first (1) step of Example 1.

[0055] (2) Preparation of 4-amino-5-methyl-4H-1,2,4-triazole-3-mercapto (intermediate 2):

[0056] As in embodiment 1 (2) step.

[0057] (3) Preparation of 1-(2-hydroxyphenyl)-3-(4-nitro)-2-propen-1-one (intermediate 3):

[0058] As in step (3) of Example 1, the difference is that X is 2-O, and R is 4-nitrobenzaldehyde.

[0059] (4) Preparation of 1-(4-nitro)-3-(4-(2-bromoethoxy)phenyl)-chalcone (intermediate 4):

[0060] As in step (4) of Example 1, the difference is that X is 2-O, and R is 4-nitrobenzaldehyde.

[0061] (5) 1-(2-(2-((4-amino-5-methyl-4H-1,2,4-triazol-3-yl)thio)ethoxy)phenyl)-3- (4-nitro)-2-propen-1-one (target compound B 3 ) preparation:

[0062] As in step...

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Abstract

The invention discloses a chalcone derivative containing thioether triazole, a preparation method and application. The structure formula of the derivative is shown as following B (the formula is shownin the description), where X is 2-O or 4-O, R is phenyl and comprises one or more substituted phenyl and heterocyclyl. The substituted phenyl is halogen at positions 2 to 6, C1-6 alkyl at positions 2to 6, C1-6 alkoxy at positions 2 to 6, nitryl at positions 2 to 6 or amino at positions 2 to 6. The heterocyclyl is furyl, thienyl, pyridyl, 3-methyl-2-pyridine, 5-methyl-2-pyridine, thiazolyl, and 4-methylthiazol-5-yl. The chalcone derivative provided by the invention has relatively good control effect on ralstonia solanacearum and bacteria of rice leaf blight.

Description

technical field [0001] The present invention relates to the field of chemical technology, in particular to a chalcone derivative containing thioethertriazole, and also to a preparation method of the chalcone derivative containing thioethertriazole, and to the sulfur-containing chalcone derivative Application of chalcone derivatives of ether triazoles in antibacterial activity. 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 be conjugated with nucleophilic groups in bacteria (such as sulfhydryl groups in proteins) to cause bacterial death. At the same time, due to the good flexibility of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/14A01N43/653A01P3/00A01P1/00
Inventor 薛伟陈英蒋仕春陈梅苏时军贺军郭涛夏榕娇王俊贺鸣
Owner GUIZHOU UNIV