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Piperazine derivatives and applications thereof

A derivative, piperazine technology, applied in the field of piperazine derivatives, can solve problems such as ligand differences

Inactive Publication Date: 2009-03-11
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, since there are homology differences between vertebrate serotonin receptors and non-vertebrate serotonin receptors, there must be differences between their ligands

Method used

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  • Piperazine derivatives and applications thereof
  • Piperazine derivatives and applications thereof
  • Piperazine derivatives and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Synthesis of 1-(6-chloropyridine-3-methyl)-4-(5-trifluoromethylpyridine-2-)piperazine

[0027] (1) Synthesis of 1-(6-chloropyridine-3-methyl)piperazine:

[0028] The reaction equation is as follows:

[0029]

[0030] A solution of 1.61g (10mmol) of 6-chloro-3-chloromethylpyridine in 10ml of absolute ethanol was slowly added dropwise in an oil bath at 50-55°C to dissolve 1.32g (15mmol) of anhydrous piperazine and 10mmol of tris In 15ml of absolute ethanol solution of ethylamine, the system was stirred for 5-6 hours, and the raw material 6-chloro-3-chloromethylpyridine was completely reacted. The solvent ethanol was evaporated to obtain the crude product, which was washed with water, extracted with dichloromethane and anhydrous Na 2 SO 4 After drying, the solvent was evaporated under reduced pressure to obtain a pure product with a yield of about 86%.

[0031] GC / MS(m / s)211(38)M + , 169(100), 126(78), 56(23).

[0032] (2) Synthesis of 1-(6-chloropyridine-3-methyl...

Embodiment 2

[0039] Synthesis of 1-(6-chloropyridine-3-methyl)-4-(5-trifluoromethylpyridine-2-)piperazine peroxide,

[0040] The reaction equation is as follows:

[0041]

[0042] In an ice bath, to a solution of 1mmol 1-(6-chloro-pyridine-3-methyl)-4-(5-trifluoromethylpyridine-2-)piperazine in 20ml of dichloromethane solution was added twice 1 mmol m-chloroperoxybenzoic acid (MCPBA). Then, the reaction system was stirred at room temperature, followed by TLC, and after 12 hours of reaction, the reaction of raw materials was complete. The reaction mixture was poured into water, extracted three times with dichloromethane, the organic phases were combined, washed with saturated brine and water, and dried over anhydrous sodium sulfate. After evaporating the solvent under reduced pressure, the crude product was obtained. The product was separated by column chromatography, eluting with dichloromethane / ethanol (v / v=8:1), and the solvent was evaporated under reduced pressure to obtain a red s...

Embodiment 3

[0046] Synthesis of 1-(2-chlorothiazole-5-methyl)-4-(3-chloro-5-trifluoromethylpyridine-2-)piperazine

[0047] (1) Synthesis of 1-(2-chlorothiazole-2-methyl)piperazine

[0048] The reaction equation is as follows:

[0049]

[0050] A solution of 1.67g (10mmol) of 2-chloro-5-chloromethylthiazole in 10ml of absolute ethanol was slowly added dropwise in an oil bath at 50-55°C to dissolve 1.32g (15mmol) of anhydrous piperazine and 10mmol of tris In 15ml of absolute ethanol solution of ethylamine, the system was stirred for 5-6 hours, and 1.67g (10mmol) of the raw material 2-chloro-5-chloromethylthiazole was completely reacted. The solvent ethanol was evaporated to obtain the crude product, which was washed with water, extracted with dichloromethane and anhydrous Na 2 SO 4 After drying, the solvent was evaporated under reduced pressure to obtain a pure product with a yield of about 87%. GC / MS(m / s)217(44)M + , 175(79), 132(100), 56(31).

[0051] (2) Synthesis of 1-(2-chloro...

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Abstract

The invention relates to a piperazine derivate and application thereof. The piperazine derivate takes N1-arylmethyl and N4-pyridyl piperazine as parent matrixes to modify the structure of pesticides of main pharmacophore of the N1-arylmethyl and N4-pyridyl piperazine, so as to obtain a type of novel compound. As shown by biological (insect disinfestation) activity determination: the novel compound designed and synthesized by the invention can effectively inhibit feeding and growth of crolepidopteron, and cause the crolepidopteron to die. The piperazine derivate not only is helpful to the further research of 5-hydroxytryptamine receptors of insects but also provides direction for creation of green pesticides with a novel functional mechanism.

Description

technical field [0001] The present invention relates to a kind of piperazine derivative and its application, specifically, to a kind of N 1 -(substituted) arylmethyl, N 4 -Substituted pyridylpiperazines and uses thereof. Background technique [0002] Insecticides are an important class of pesticides and play a very important role in agricultural production. With the increasing concern of the public on environmental protection and ecological balance and the problem of resistance to existing pesticides, it is increasingly urgent to create green pesticides with new mechanisms of action. [0003] Serotonin is a very important class of biological amine neurotransmitters, which can participate in the regulation of many important physiological activities of vertebrates by acting on serotonin receptors. Therefore, serotonergic ligands have important pharmacological significance in the field of medicine. [0004] Studies have shown that serotonin is also an important neurotransmi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/74C07D277/32C07D417/12A01N43/60A01P5/00A01P7/00
Inventor 李忠宋恭华蔡明沂黄青春彭延庆
Owner EAST CHINA UNIV OF SCI & TECH
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