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Oxazole ring containing 2,4-disubstituted pyrazole compound, preparation method therefor and application of oxazole ring containing 2,4-disubstituted pyrazole compound

A compound, pyrazole technology, applied in the field of synthesis of heterocyclic compounds, can solve the problem of less research and application of compounds, and achieve the effect of high yield and simple preparation method

Active Publication Date: 2017-04-19
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] In addition, there are few studies and applications on compounds containing two excellent active centers of oxazole ring and pyrazole ring at the same time.

Method used

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  • Oxazole ring containing 2,4-disubstituted pyrazole compound, preparation method therefor and application of oxazole ring containing 2,4-disubstituted pyrazole compound
  • Oxazole ring containing 2,4-disubstituted pyrazole compound, preparation method therefor and application of oxazole ring containing 2,4-disubstituted pyrazole compound
  • Oxazole ring containing 2,4-disubstituted pyrazole compound, preparation method therefor and application of oxazole ring containing 2,4-disubstituted pyrazole compound

Examples

Experimental program
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Effect test

Embodiment 1

[0042] 2-(2'-hydroxyphenyl)-4-(1'-1H-pyrazole)oxazole-4-carboxamide (formula A-1) and 2-(2'-hydroxyphenyl)-4-( Preparation of 1'-1H-3,5-dimethylpyrazole)oxazole-4-carboxamide (Formula B-1)

[0043]

[0044]Add 7.5mmol pyrazole and 10ml methylene dichloride in a 50ml three-necked flask equipped with a thermometer, stir and cool to 0°C, add dropwise 10% (wt.) sodium hydroxide aqueous solution containing 7.5mmol sodium hydroxide, control the rate of addition, Keep the temperature around 0°C. After the dropwise addition was completed, stir for 30 min. While maintaining the system temperature at 0°C, a methylene chloride solution containing 7.5 mmol of 2-hydroxyphenyloxazolecarbonyl chloride and a 10% (wt.) sodium hydroxide aqueous solution containing 7.5 mmol of sodium hydroxide were added dropwise. Control the rate of addition so that both are added at the same time. After the dropwise addition, slowly rise to room temperature and react at 25°C for 9.5-10h. After filtering...

Embodiment 2

[0057] Inhibitory activity of oxazole ring-containing 2,4-disubstituted-pyrazole compounds shown in embodiment 2 formula I to phosphodiesterase 4 (PDE4)

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Abstract

The invention discloses an oxazole ring containing 2,4-disubstituted pyrazole compound. The structural formula of the compound is represented by a formula I shown in the description, wherein the quantity of R is 1, R is H, halogen, nitro, hydroxyl or C1-4 alkyl or alkoxy, and R1 and R2 are the same or different and are independently selected from H and C1-4 alkyl or alkoxy separately. The invention simultaneously provides a preparation method for the compound and an application of the compound. The oxazole ring containing 2,4-disubstituted pyrazole compound provided by the invention has good bioactivity and can serve as a phosphodiesterase (PDE4) and TNF[alpha] inhibitor; and the preparation method is simple and is high in yield, and the application of oxazole and pyrazole structures in the aspect of serving as phosphodiesterase (PDE4) and TNF[alpha] inhibitors is extended.

Description

technical field [0001] The invention belongs to the field of synthesis of heterocyclic compounds, and in particular relates to a 2,4-disubstituted pyrazole compound containing an oxazole ring and a preparation method and application thereof. Background technique [0002] In recent years, heterocyclic compounds have played an important role in the creation of new ultra-high-efficiency pesticides. When looking for compounds with novel structures and biological activities, designing and synthesizing various heterocyclic compounds is one of the very important ways, and has become quite active. Fields: (a) New Heterocyclic Pesticides-Fungicides, edited by Baoan Song, Chemical Industry Press, 2009; (b) New Heterocyclic Pesticides-Insecticides, edited by Baoan Song and Linjiang Jin, Chemical Industry Press, 2010; (c) New Heterocyclic Pesticides-Herbicides, edited by Song Baoan and Wu Jian, Chemical Industry Press, 2011. Among heterocyclic compounds, nitrogen-containing heterocycli...

Claims

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Application Information

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IPC IPC(8): C07D413/06A61K31/422A61P25/28A61P25/16A61P11/00
CPCC07D413/06
Inventor 崔紫宁李亚胜胡德坤田浩刘星宇宋高鹏
Owner SOUTH CHINA AGRI UNIV
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