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Phenanthrene and dihydrophenanthrene compounds and application thereof

A compound, the technology of hydroxydihydrophenanthrene, which is applied in the field of phenanthrene and dihydrophenanthrene compounds, can solve the problems of large toxic side effects and poor specificity

Inactive Publication Date: 2013-11-27
CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing anti-inflammatory drugs have disadvantages such as poor specificity and relatively large toxic and side effects.

Method used

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  • Phenanthrene and dihydrophenanthrene compounds and application thereof
  • Phenanthrene and dihydrophenanthrene compounds and application thereof
  • Phenanthrene and dihydrophenanthrene compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Extraction, separation and structural identification of compounds

[0031] 1.1 Instruments, reagents and fillers

[0032]UV1902 ultraviolet spectrophotometer; polarimetry using Perkin-Elmer 341 polarimeter; Perkin-Elmer FT-IR infrared spectrophotometer, KBr pellets; circular dichroism (CD) measurement using JASCO J-810; nuclear magnetic resonance experiment Bruker Avance 600 nuclear magnetic resonance instrument was used; mass spectrometry was determined using Bruker Daltonics Bio-TOF-Q type; high performance liquid chromatography: Agilent 1260 HPLC, and the preparative column used Kromasil 100-10-C18.

[0033] Methanol (analytical pure): Chengdu Kelong Chemical Reagent Factory; Chloroform (analytical pure): Chongqing Jiyuan Chemical Co., Ltd.; Ethyl acetate (analytical pure): Tianjin Jinkangde Technology Co., Ltd.; n-Butanol (analytical pure): Chengdu City Kelong Chemical Reagent Factory; petroleum ether (analytical pure): Tianjin Kangde Technology Co., Ltd...

Embodiment 2

[0081] Embodiment 2: the synthetic preparation of compound of the present invention

[0082] The general formula compound I of the present invention can be according to the following scheme figure 1 To prepare, wherein the substituent R 8 , R 9 , R 10 The substituents in the compounds of general formula I are as defined above.

[0083]

[0084] Add compound A (3.5mmol) and compound B (7mmol) into a 50mL two-necked bottle, connect it to a reflux condenser, pump air, and protect it with nitrogen. After adding acetic anhydride (20 mL) and triethylamine (5 mL) via needle injection, the mixture was reacted under reflux for 6 hours. After the reaction, the reaction solution was slowly poured into a beaker filled with a large amount of ice water, and kept stirring, at which point solids were precipitated. After the mixture was filtered, the resulting solid was recrystallized from ethanol to give compound C.

[0085] Compound C (5.56 mmol), copper powder (28.8 mmol) and quino...

Embodiment 3

[0100] Example 3: The NO production-inhibiting activity of the compounds of the present invention.

[0101] 3.1 Materials

[0102] Compound (1-33); mouse RAW264.7 macrophages; endotoxin (LPS 1 μg / mL); BAY (10 μM, positive control) NO detection kit (Beyotime, Haimen, China);

[0103] 3.2 Main Instruments

[0104] Fluorescent microplate reader (Thermo Scientific, Waltham, MA, USA)

[0105] 3.3 Method

[0106] 3.3.1 Measurement of NO production by LPS-stimulated RAW264.7 macrophages

[0107] Inoculate RAW264.7 macrophages in 96-well plate, inoculate 1×10 per well 4 After the cells were inoculated and attached to the wall, the compound to be tested (1-8) was added and incubated for 2 hours, and then LPS (final concentration: 1 μg / mL) was added and incubated for 24 hours. Finally, take the 96-well plate culture medium and use the NO kit to detect the NO content by measuring its OD 550 To represent. Three replicate wells were taken for each experiment, and the experiment was ...

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Abstract

The invention relates to phenanthrene and dihydrophenanthrene compounds and an application thereof. The phenanthrene or dihydrophenanthrene compounds can effectively inhibit inflammatory factors and also can inhibit NF (nuclear factor)-kappa B and MAPKs (Mitogen Activated Protein Kinase) signal channels. The compounds or medically acceptable salts, solvates, clathrate compounds or prodrugs thereof can be applied to serving as medicines for treating inflammations and also can be applied to serving as medicines for treating NF-kappa B and MAPKs signal channel related diseases.

Description

technical field [0001] The invention relates to novel pharmaceutically useful phenanthrene and dihydrophenanthrene compounds, and the application of these compounds in the preparation of medicines for treating inflammation and diseases related to NF-κB and MAPKs signaling pathways. Background technique [0002] Inflammation is the body's normal defense response process to endogenous or exogenous injury factors, mainly mediated by activated immune cells. Under normal physiological conditions, the inflammatory response is beneficial to the body. It can kill and kill invading pathogenic microorganisms, eliminate exogenous stimuli, and promote the repair and healing of damaged tissues. However, when the body's self-regulating ability is out of balance, it will The uncontrolled inflammatory response can lead to many diseases, such as arthritis, septic shock, type 2 diabetes, bronchial asthma and senile dementia. Early inflammatory responses lead to increased capillary permeabili...

Claims

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Application Information

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IPC IPC(8): C07H15/24C07H1/08C07C43/23C07C41/34C07H1/00C07C41/20C07C255/54C07C253/30C07C255/55C07C205/35C07C201/12C07C69/63C07C67/283A61K31/704A61K31/085A61K31/222A61K31/277A61P29/00A61P1/04A61P1/00A61P37/08A61P25/06A61P31/04A61P31/12A61P31/10A61P9/10A61P19/02A61P19/08A61P37/02A61P1/18A61P13/12A61P27/02
Inventor 张国林王飞淳泽林源
Owner CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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