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Substituted phenylfuran formylpyrazole compound as well as preparation method and application of compound

A technology of phenylfuroylpyrazoles and dimethylpyrazoles, which is applied in the field of synthesis of heterocyclic compounds, and achieves the effects of novel structure, simple preparation method and high yield

Active Publication Date: 2018-03-20
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although some drugs have been developed for the treatment of these two diseases to alleviate the suffering of patients, there are no drugs and methods that can cure these two diseases

Method used

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  • Substituted phenylfuran formylpyrazole compound as well as preparation method and application of compound
  • Substituted phenylfuran formylpyrazole compound as well as preparation method and application of compound
  • Substituted phenylfuran formylpyrazole compound as well as preparation method and application of compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: the preparation of compound 1-3

[0039] Add 15mmol 3,5-dimethylpyrazole and 10mL dichloromethane into a 50mL three-necked flask equipped with a thermometer, and add 10% (wt.) sodium hydroxide aqueous solution containing 15mmol sodium hydroxide dropwise at room temperature to control the dropping rate At one drop per second, keep the temperature at room temperature. After the sodium hydroxide aqueous solution was added dropwise, 10 mL of dichloromethane solution containing 7.5 mmol 5-(4-chlorophenyl)-2-furoyl chloride was added dropwise, and the dropping rate was controlled at one drop per second. After the dropwise addition, slowly raise the temperature to 50°C, and react at 50°C for 3-10 hours. After the reaction was completed, filter to remove the precipitate, and rotate the filtrate to remove the solvent to obtain a light yellow solid. Compound I-3 was obtained by separation on a silica gel column (eluent: petroleum ether / ethyl acetate V / V=5 / 1), yiel...

Embodiment 2

[0045]Example 2 Inhibitory activity of compounds in Table 1 on phosphodiesterase IV.

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Abstract

The invention provides a substituted phenylfuran formylpyrazole compound. The structural general formula of the compound is represented by a formula (I) as shown in the description, wherein R radicalrepresents one or more of hydrogen, halogen, nitryl, hydroxy, C1-C4 alkyl or alkoxy. The compound provided by the invention has the beneficial effects that a preparation method is simple, the yield ishigh, the structure is novel, the compound further has good PDE4 inhibiting activity, and the inhibitory effect can optimally reach that IC50 is 1.7+ / -0.3 microns; and the compound is as a PDE4 inhibitor and has potential application values in the prevention and treatment of diseases regulated and controlled by phosphodiesterase, such as the treatment of diseases of asthma and chronic pulmonary obstruction.

Description

technical field [0001] The invention belongs to the field of synthesis of heterocyclic compounds, and in particular relates to a substituted phenylfuroylpyrazole compound and its preparation method and application. Background technique [0002] Phosphodiesterase IV (PDE4) is the main enzyme involved in the metabolism of cyclic adenosine monophosphate (cAMP) in immune, inflammatory and airway smooth muscle cells. It can specifically hydrolyze cAMP to generate 5'-AMP, reduce the level of intracellular cAMP, and make intracellular cAMP / cGMP ratio imbalance, which triggers asthma ( Brain Res. Bull. 2016, 122 , 255-262; Li Feng, 2008, Master Thesis of Shandong University). [0003] Chronic obstructive pulmonary disease and asthma are two common respiratory diseases, which have become serious threats to people's health worldwide ( Bioorg. Med. Chem. Lett , 2015, 25, 4610-4614). Chronic obstructive pulmonary disease (chronic obstructive pulmonary disease, COPD) is a serious c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/06A61P11/06A61P11/00
CPCC07D405/06
Inventor 崔紫宁胡德坤宋高鹏向绪稳陶辉刘星宇
Owner SOUTH CHINA AGRI UNIV