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2, 5-bis (2, 6-difluorobenzylidene)-cyclopentanone and preparation method and application thereof

A technology of difluorobenzylidene and cyclopentanone, which is applied in the direction of condensation preparation of carbonyl compounds, digestive system, endocrine system diseases, etc.

Pending Publication Date: 2020-12-11
THE SECOND HOSPITAL AFFILIATED TO WENZHOU MEDICAL COLLEGE
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although the exact etiology of NAFLD is unknown, the effects of hepatic glucocorticoids may be related to metabolic syndrome and NAFLD
However, there is no report on the treatment of NAFLD by inhibiting the 11β-HSD1 enzyme activity without affecting the 11β-HSD2 activity.

Method used

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  • 2, 5-bis (2, 6-difluorobenzylidene)-cyclopentanone and preparation method and application thereof
  • 2, 5-bis (2, 6-difluorobenzylidene)-cyclopentanone and preparation method and application thereof
  • 2, 5-bis (2, 6-difluorobenzylidene)-cyclopentanone and preparation method and application thereof

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preparation example Construction

[0033] The invention provides the preparation method of the 2,5-bis(2,6-difluorobenzylidene)-cyclopentanone, see Figure 6 , including the following steps:

[0034] Mix cyclopentanone with the structure shown in formula II and 2,6-difluorobenzaldehyde with the structure shown in formula III in a solvent, use sodium methoxide as a catalyst, and generate aldehydes and ketones at 20-30°C Condensation reaction, the reaction lasts for 12 to 16 hours, and the reactant is separated and purified to obtain a yellow powder product;

[0035]

[0036] In the present invention, the molar mass ratio of cyclopentanone, 2,6-difluorobenzaldehyde and sodium methoxide is preferably 1:18-22:24-28, more preferably 1:20:26. The solvent is preferably ethanol or methanol.

[0037] In the present invention, the separation and purification method of the reactant is preferably to filter the obtained reactant in ice water, collect the retentate, wash with water, and evaporate to dryness under reduce...

Embodiment 1

[0044] Dissolve 2.08 mmol of cyclopentanone with the structure of formula II in 100 mL of absolute ethanol, stir at room temperature for 5 minutes, then add 42.2 mmol of 2,6-difluorobenzaldehyde with the structure of formula III, and continue stirring for 10 minutes, the solution remains unchanged. Continue to slowly drop 15 mL of sodium methoxide (NaOMe) solution (containing 54.8 mmol of sodium methoxide) into the reaction solution, stir at 25° C. for 14 h, pour the mixture into ice water (150 mL) and filter. After filtration, it was washed twice with water (20 mL) and evaporated to dryness under reduced pressure. followed by CH 2 Cl 2 or CH 3 Wash twice with OH (20 mL), and dry in vacuo at 30°C to obtain a yellow powder product, which is purified by silica gel column chromatography to obtain a compound of formula I with a purity greater than 79.2%;

[0045]

[0046] The compound of formula I is subjected to structural characterization, and the results are as follows: ...

Embodiment 2

[0048] Compounds with Formula I Selectively Inhibit 11β-Hydroxysteroid Dehydrogenase 1 Activity Experiment

[0049] Human kidney and liver microsomes were purchased from a genetic testing company, and rat and mouse kidney and liver microsomes were directly prepared and extracted (Guo, J., Yuan, X., Qiu, L., Zhu, W., Wang, C., Hu, G., Chu, Y., Ye, L., Xu, Y., and Ge, R.S., 2012. Inhibition of human and rat 11beta-hydroxysteroid dehydrogenases activities by bisphenol A. Toxicol Lett 215, 126-130).

[0050] Treat the liver and kidney microsomes (10 μg) of rats, mice and people with the formula I structural compound prepared in 100 μM embodiment 1 for 30 minutes, then use radioimmunoassay technique (Ge, R.S., Dong, Q., Niu, E .-M.,Sottas,C.M.,Hardy,D.O.,Catterall,J.F.,Latif,S.A.,Morris,D.J.,and Hardy,M.P.,2005.11b-Hydroxysteroid dehydrogenase 2 in rat Leydig cells:its role in bluntingglucocorticoid action at physiological le substrate. Endocrinology 146, 2657-2664) was used to de...

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Abstract

The invention provides 2, 5-bis (2, 6-difluorobenzylidene)-cyclopentanone and a preparation method and application thereof, and belongs to the technical field of chemical medicines. 2, 5-bis (2, 6-difluorobenzylidene)-cyclopentanone can selectively inhibit the activity of 11beta-HSD1 without influencing the activity of 11beta-HSD2, reduce the blood fat level and liver lipid content of a high-fat diet induced non-alcoholic fatty liver disease mouse, and resist insulin rise of the high-fat diet induced non-alcoholic fatty liver disease mouse; the purpose of effectively treating the non-alcoholicfatty liver disease induced by the high-fat diet by taking the compound as an active ingredient is achieved. Therefore, the invention provides the application of the 2, 5-bis (2, 6-difluorobenzylidene)-cyclopentanone in preparing the medicine for preventing and / or treating the non-alcoholic fatty liver disease.

Description

technical field [0001] The invention belongs to the technical field of chemical medicines, and specifically relates to 2,5-bis(2,6-difluorobenzylidene)-cyclopentanone and its preparation method and application. Background technique [0002] Non-alcoholic fatty liver disease (NAFLD) is a common human disease and a metabolic syndrome of the liver (Nakajima and Naito, 2015), which is closely related to our lifestyle and diseases, such as High-fat diet, type 2 diabetes, dyslipidemia, hyperadrenocorticoid, obesity, hypertension (Nakajima and Naito, 2015). Because of impaired lipid metabolism and glucose metabolism in the liver, excessive intake of high-fat diets (HFD) can lead to accumulation of lipids in the liver, and high-fat diets (HFD) are considered to be the main risk of NAFLD and a series of complications One of the factors (Nakajima and Naito, 2015). [0003] Some lipid-binding proteins may be related to the occurrence and development of NAFLD, one of which is perilipi...

Claims

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Application Information

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IPC IPC(8): C07C49/697C07C45/45A61P5/48A61P1/16
CPCC07C49/697A61P5/48A61P1/16
Inventor 王义炎葛仁山李慧涛朱琦琦李晓珩
Owner THE SECOND HOSPITAL AFFILIATED TO WENZHOU MEDICAL COLLEGE
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