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Kirenol derivative and application thereof in preparation of proinflammatory cytokine inhibitor

A physiological and compound technology, applied in the direction of drug combination, active ingredients of hydroxyl compounds, medical preparations containing active ingredients, etc., can solve the problems of not affecting the process of joint damage, long-term tolerance and limited effectiveness

Inactive Publication Date: 2009-12-09
YANTAI TARGET DRUG RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These two types of drugs mainly inhibit the synthesis of prostaglandins in different links, and both cannot affect the joint damage process, and their long-term tolerance and effectiveness are also limited (Tan Wei. Medication problems for rheumatoid arthritis. Medical Herald, 1997, 16:142)

Method used

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  • Kirenol derivative and application thereof in preparation of proinflammatory cytokine inhibitor
  • Kirenol derivative and application thereof in preparation of proinflammatory cytokine inhibitor
  • Kirenol derivative and application thereof in preparation of proinflammatory cytokine inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Preparation and Structure Identification of Chinonyl Alcohol Derivatives

[0055] 1. Dissolve 20 mg of chinonanol in 1 ml of acetone, add 20 μl of 2,2-dimethoxypropane and a catalytic amount of p-toluenesulfonic acid, and stir at room temperature for 20 minutes. A certain amount of water was added to the reaction mixture, and then extracted three times with ethyl acetate. The ethyl acetate phase was extracted with saturated sodium bicarbonate solution to remove p-toluenesulfonic acid present in the reaction as a catalyst, then extracted with saturated brine to remove water, and finally dried over anhydrous sodium sulfate overnight. The ethyl acetate phase dried overnight was concentrated, dissolved in dichloromethane and subjected to silica gel column chromatography, eluted with petroleum ether-acetone system (3:1) to obtain 15,16-isopropylidene chinonanol (compound 1) 18 mg, yield 90%.

[0056] Compound 1: C 23 h 28 o 5 (Mr. 378), white solid, mp. 198-200°C. MS (...

Embodiment 2

[0088] Experimental Study on Inhibition of the Release of Proinflammatory Factors TNF-α and IL-1β by Chinonyl Derivatives in Vitro

[0089] Experimental Materials:

[0090] 1. Cells: normal human peripheral blood mononuclear cells (PMBC)

[0091] Drugs to be tested: Chinonanol and its derivatives, separated and prepared by Shandong Target Drug Research Company.

[0092] 2. Positive control: dexamethasone (product of Sigma, USA)

[0093] 3. Reagents: Ficoll-Paque Plus (Amersham Bioscience); Endotoxin (LPS, Escherichia coli0111: B4, Sigma) and dexamethasone (DEX, CalBiochem); ELISA assay kit for TNF-α and IL-1β (Jingmei Biological engineering company); dimethyl sulfoxide (DMSO, Sigma); trypsin (Amresco); RPMI1640 medium, penicillin, streptomycin and fetal bovine serum (Gibco).

[0094] 4. Instrument: CKX31 inverted microscope (Olympus); constant temperature CO 2 Incubator (Thermo); 5810R desktop high-speed low-temperature centrifuge (Eppendorf); automatic microplate reader (...

Embodiment 3

[0111] Experimental Study on Inhibition of NO Release from RAW264.7 Cells by Chinonyl Alcohol Derivatives

[0112] Experimental Materials:

[0113] 1. Cells: mouse mononuclear macrophage cell line RAW264.7, purchased from Shanghai Cell Bank of Chinese Academy of Sciences (ATCC)

[0114] Drugs to be tested: Chinonanol and its derivatives, separated and prepared by Shandong Target Drug Research Company.

[0115] 2. Reagents: RPMI1640 medium, penicillin, streptomycin, and fetal bovine serum were purchased from Gibco; trypsin was purchased from Amresco; LPS (Escherichia coli 0111: B4) was purchased from Sigma. Other commonly used reagents were domestic analytical grade.

[0116] 3. Instrument: CKX31 inverted microscope (Olympus); constant temperature CO 2 Incubator (Thermo); 5810R desktop high-speed low-temperature centrifuge (Eppendorf); automatic microplate reader (Biotek).

[0117] experimental method:

[0118] RAW264.7 cells with 10% fetal bovine serum, 100 μg mL -1 Stre...

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Abstract

The invention relates to a Kirenol derivative and an application thereof in preparation of a proinflammatory cytokine inhibitor. The Kirenol derivative shown in a general formula (I) and a general formula (II) can inhibit the proinflammatory cytokine tumor necrosis factor (TNF)-alpha, the interleukin (IL)-1beta and the inflammatory molecule nitrogen oxide and is suitable for drug preparation.

Description

technical field [0001] The present invention relates to chinnonyl alcohol derivatives and their medical applications. Background technique [0002] Inflammation is a defense-based response of living tissue with vascular system to damage caused by various inflammatory factors. Because of the vascular system, its response to injury not only retains the above-mentioned simple form, but also further forms a local and systemic defense response centered on vascular response. Vascular reaction causes fluid and leukocytes in blood vessels to leak into the injury site, confine and kill injury factors, remove and absorb necrotic tissue, and make the body's defense response more complex and perfect. Vascular responses are a major feature of the inflammatory process and a central link in defense. While resisting damage, the body repairs damaged tissues through the regeneration of parenchymal cells (arenehymaleell) and interstitial cells (mesenehymaleell). Inflammation is essentially ...

Claims

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Application Information

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IPC IPC(8): C07C35/42C07D317/14A61K31/045A61K31/357A61P1/00A61P9/10A61P3/10A61P25/00A61P35/00A61P37/00
Inventor 刘珂关玉昆梁冬冬赵烽许卉刘军锋
Owner YANTAI TARGET DRUG RES
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