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4‑Chloro‑2‑(5‑phenyl‑1‑(pyridine‑2‑yl)‑4,5‑dihydro‑1h‑pyrazole‑3‑yl)phenol in pharmaceutical applications

A technology of phenyl and pyridine, applied in 4-chloro-2-(5-phenyl-1-(pyridin-2-yl)-4,5-dihydro-1H-pyrazole-3-yl)phenol Fields of application in pharmaceuticals

Active Publication Date: 2017-02-15
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At the same time, using the biological activity and autofluorescence properties of 4-chloro-2-(5-phenyl-1-(pyridin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)phenol , to study its mechanism of action in fatty liver and arteriosclerosis and its application in the preparation of drugs for inhibiting fatty liver and stabilizing arteriosclerotic plaque, which has not been reported yet

Method used

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  • 4‑Chloro‑2‑(5‑phenyl‑1‑(pyridine‑2‑yl)‑4,5‑dihydro‑1h‑pyrazole‑3‑yl)phenol in pharmaceutical applications
  • 4‑Chloro‑2‑(5‑phenyl‑1‑(pyridine‑2‑yl)‑4,5‑dihydro‑1h‑pyrazole‑3‑yl)phenol in pharmaceutical applications
  • 4‑Chloro‑2‑(5‑phenyl‑1‑(pyridine‑2‑yl)‑4,5‑dihydro‑1h‑pyrazole‑3‑yl)phenol in pharmaceutical applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Example 1: Preparation of 4-chloro-2-(5-phenyl-1-(pyridin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)phenol (FPD5)

[0061] To a solution of chalcone (1.0 mmol) in ethanol (15 mL) was added 2-hydrazinopyridine (1.2 mmol) and sodium hydroxide (3.0 mmol). The reaction mixture was continued to reflux for 4 hours. The progress of the reaction was monitored by thin layer chromatography. After the reaction is complete, cool to room temperature, dilute with cold water, and neutralize with hydrochloric acid. After filtration, the resulting crude product was washed with water and ethanol, and recrystallized from ethanol. Yield 36.0%, mp: 172-173°C.

[0062] IR(KBr,cm -1 ):3066.0, 3031.5, 1588.9, 1476.0, 1443.9, 1255.9, 1145.2, 760.4, 692.9; 1 H NMR (400MHz, CDCl 3 ): δ3.28 (dd, 1H, J=5.6, 17.4Hz, 4-H trans ), 3.89 (dd, 1H, J=12.4, 17.4Hz, 4-H cis ), 5.81 (dd, 1H, J = 5.6, 12.4Hz, 5-H of pyrazoline), 6.70 (dd, 1H, J = 5.3, 6.7Hz, pyridine-H), 6.99 (d, 1H, J = 8.8Hz ,Ar-H),7.12(d,...

Embodiment 2

[0063] Example 2: FPD5 to apoE - / - Effects of Fatty Liver in Mice

[0064] Based on previous experiments, it has been shown that FPD5 (0.01μM-0.5μM) can interact with esterase D (ESD), promote the activity of ESD, and at the same time, effectively inhibit the liver cells caused by oxidized low-density lipoprotein cholesterol (ox-LDL). Downregulation of ESD activity (see figure 1 ), the applicant chose doses of 5 μg / kg / day and 20 μg / kg / day to explore the effects of FPD5 on the stability of fatty liver and atherosclerotic plaque.

[0065] apoE - / - Mice (purchased by Beijing Weitong Lihua Experimental Animal Technology Co., Ltd.) were fed with high-fat diet (formula: 0.25% cholesterol+15% lard+85% common feed) until the end of sampling.

[0066] Experimental mice were randomly divided into four groups: baseline group (no injection), control group (DMSO solvent / PBS: v / v=1:4, 100 μL), FPD5 high-dose group (20 μg / kg / day), FPD5 low dose group (5μg / kg / day).

[0067] The baseline ...

Embodiment 3

[0071] Example 3 FPD5 to apoE - / - Effects of Arterial Plaque Size in Mice

[0072] The aortic root isolated in Example 2 was frozen and embedded and sectioned for later use. The aorta was sectioned longitudinally, rinsed with PBS, and fixed in 10% neutral formalin for later use. The longitudinally sectioned aorta was stained with oil red O, and the sections were fixed with calcium formaldehyde for 10 minutes; washed three times with distilled water; dehydrated in 60% isopropanol for 1 minute; put in oil red O staining solution, and stained in a constant temperature box at 60°C for 20- 30min; decolorize the slices in 60% isopropanol for 1min; wash in distilled water for 1min; stain with hematoxylin for 30s; wash in distilled water for 1min; differentiate with 1% hydrochloric acid alcohol for 3s; The plaque area and vessel wall area were measured using ImagePro image analysis software, and the plaque / vessel wall area ratio was calculated. The frozen section of aortic root carr...

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Abstract

The invention discloses application of 4-chloro-2-(5-phenyl-1-(pyridine-2-yl)-4, 5-dihydro-1H-pyrazol-3-yl) phenol in preparation of medicaments for inhibiting fatty liver and stabilizing atherosclerotic plaques. The dose of 4-chloro-2-(5-phenyl-1-(pyridine-2-yl)-4,5-dihydro-1H-pyrazol-3-yl) phenol for effectively inhibiting the fatty liver and stabilizing the atherosclerotic plaques is 5-20mu g / kg / day. 4-chloro-2-(5-phenyl-1-(pyridine-2-yl)-4, 5-dihydro-1H-pyrazol-3-yl) phenol provided by the invention lays a foundation for development of the medicaments for treating the fatty liver and arteriosclerosis and can be used as a powerful tool for researching a molecular mechanism of abnormal lipid metabolism and unstable atherosclerotic plaques.

Description

technical field [0001] The present invention relates to a pharmaceutical use of pyrazoline derivatives, in particular to 4-chloro-2-(5-phenyl-1-(pyridin-2-yl)-4,5-dihydro-1H-pyrazole- Application of 3-base) phenol in the preparation of drugs for inhibiting fatty liver or stabilizing arteriosclerotic plaque. Background technique [0002] The structural formula of 4-chloro-2-(5-phenyl-1-(pyridin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)phenol is: [0003] [0004] Molecular formula: C 20 h 16 ClN 3 o [0005] Molecular weight: 349.81, properties: light yellow solid, melting point: 172-173°C. [0006] Pyrazoline compounds have a wide range of biological activities and can be used as antibacterial, anti-inflammatory, analgesic, anticancer and anticonvulsant drugs. At present, some of these compounds have been used as clinical drugs. Among them, the most representative one is 1-(3-trifluoromethylphenyl)-3-aminopyrazoline, which has a good anti-inflammatory effect. Therefore, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/4439A61P1/16A61P9/10
CPCA61K31/4439
Inventor 苗俊英赵宝祥张尚立苏乐赵静邵婧
Owner SHANDONG UNIV
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