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Diaryl ether compound, preparation method and application thereof

A compound and technology of diaryl ether, applied in the field of diaryl ether compound and its preparation, can solve the problem of lack of anti-tumor drugs, etc., and achieve the effect of simple and easy preparation method, easy-to-obtain raw materials, and less stringent preparation conditions

Active Publication Date: 2019-01-04
PEKING UNIV SHENZHEN GRADUATE SCHOOL
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Despite progress in the diagnosis and treatment of tumors, there is still a lack of anti-tumor drugs that can effectively block the energy supply of tumor cells at the source

Method used

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  • Diaryl ether compound, preparation method and application thereof
  • Diaryl ether compound, preparation method and application thereof
  • Diaryl ether compound, preparation method and application thereof

Examples

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preparation example Construction

[0045] The preparation method A of the above-mentioned diaryl ether compound comprises the following steps:

[0046] S110. Nucleophilic substitution reaction of compound A1 and compound A2 to generate compound A3.

[0047] In one embodiment, under alkaline conditions, compound A1 and compound A2 were dissolved in an organic solvent, stirred and reacted at 70°C-90°C for 12h-24h, and compound A3 was obtained after separation and purification.

[0048] Compound A1 is p-fluoronitrobenzene, its structural formula is

[0049] The structural formula of compound A2 is Among them, -X- is -CH- or -N-, -R 1 ,-R 2 ,-R 3 independently selected from -H, -F, -Cl, -Br, alkoxy, aryl, aryloxy, N,N-dialkylamino, N-alkyl-N-acylamino, pyridyl, imidazole One of base, pyrazolyl, furyl, pyrrolyl, morpholinyl, N-alkylpiperazinyl, piperidinyl and tetrahydropyrrolyl.

[0050] Specifically, compound A2 is selected from 4-(nitrogen-allylbutanylamino)phenol, 4-(nitrogen-allylbenzylamido)phenol, 4-(n...

Embodiment 1～34

[0108] Examples 1-29 The above-mentioned diaryl ether compounds were prepared by the preparation method A. The specific parameters of the preparation are shown in Table 1, and the specific steps are as follows:

[0109] Step 1, 10.0mmol p-fluoronitrobenzene and compound A2 are dissolved in acetonitrile, the molar ratio of p-fluoronitrobenzene and compound A2 is C2, and potassium carbonate is added to the above solution, potassium carbonate and p-fluoronitrobenzene The molar ratio is C3, and the mixture is stirred and reacted for 18h at the temperature indicated by C1. Then cool to room temperature, add 40mL water to dilute the reaction solution, extract with 3×40mL ethyl acetate, combine the organic phases and wash with 2×50mL saturated brine, dry over anhydrous sodium sulfate, and concentrate in vacuo, the obtained residue is passed through a silica gel column Purification by chromatography (eluent: n-hexane / ethyl acetate=10:1) gave Compound A3.

[0110] Step 2. Dissolve 2....

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Abstract

The invention relates to a diaryl ether compound , a preparation method and application thereof, wherein the diaryl ether compound has the following structural formula: (the formula is shown in the description), wherein, -X- is CH- or -N-; =R1,-R2,-R3 are independently selected from one kind of H-,-F,-Cl,-Br, alkoxy, aryl, aryloxy, N, N-Dialkylamino, N-Alkyl-N-Acylamino, pyridyl, imidazolyl, pyrazolyl, furyl, pyrrolyl, morpholinyl, N-Alkyl piperazinyl, piperidinyl and tetrahydropyrrolyl. The diaryl ether compound has the advantage of inhibiting the activity of a PFKFB3 in the tumor cells, effectively blocking the activation of the key enzyme during the glycolysis process, thereby blocking energy supply from the energy source of the tumor cells, and providing a new medicament for the effective treatment of the tumor diseases.

Description

technical field [0001] The invention relates to the field of organic compounds, in particular to a diaryl ether compound and its preparation method and application. Background technique [0002] Tumor cells are abnormal cells that can reproduce and regenerate rapidly, and have the characteristics of unlimited proliferation, transformation and easy transfer. The energy metabolism of normal cells is mainly completed by the oxidative phosphorylation of glucose in the mitochondria. The energy metabolism of tumor cells is different from that of normal cells. Tumor cells mainly obtain energy to satisfy tumor cells through a large amount of glucose uptake and glycolysis (Warburg effect). growth and proliferation. The glycolysis pathway is the main metabolic pathway in almost all organisms. The expression, activity and regulation of receptors, transport molecules and key enzymes in the glycolysis process play a vital role in the occurrence, development, metastasis and regression of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/16C07D403/12A61K31/40A61K31/4178A61P35/00
CPCC07D207/16C07D403/12
Inventor 车超许正双全军民黄湧洪梅李勤凯霍玉庆李志明杨震
Owner PEKING UNIV SHENZHEN GRADUATE SCHOOL
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