Flavanonol compound containing N aromatic heterocycte and preparation method and application thereof

A technology of dihydroflavonols and aromatic heterocycles, applied in organic chemistry, drug combination, antipyretics, etc., can solve problems such as side reactions and achieve strong anti-inflammatory effects

Active Publication Date: 2018-01-26
HUBEI UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Anti-inflammatory drugs currently used clinically include non-steroidal anti-inflammatory drugs, steroidal anti-inflammatory drugs, immunosuppressive drugs, etc. These drugs have playe

Method used

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  • Flavanonol compound containing N aromatic heterocycte and preparation method and application thereof
  • Flavanonol compound containing N aromatic heterocycte and preparation method and application thereof
  • Flavanonol compound containing N aromatic heterocycte and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: 2-(3 / Total Synthesis of -pyridyl)-3,5,7-trihydroxychroman-4-one

[0024] (1) Preparation of 2,4-dimethoxymethoxy-6-hydroxyacetophenone

[0025]

[0026] Dissolve 1g of 2,4,6-trihydroxyacetophenone in 30ml of acetone, add 2.88g of anhydrous potassium carbonate, reflux and stir for 30min, cool slightly, add 1.13ml of chloromethyl ether dropwise, continue to reflux, TLC plate detects the reaction After completion, the reaction was quenched by adding water, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and rotary evaporated to obtain 1.32 g of 2,4-dimethoxymethoxy-6-hydroxyacetophenone with a yield of 86.62%.

[0027] (2) 3-pyridyl-2 / ,4 / -Dimethoxymethoxy-6 / - Preparation of hydroxychalcone

[0028]

[0029] Dissolve 0.72g of 3-pyridinecarbaldehyde in 25mL of anhydrous methanol, add 5.20mL of 50% sodium hydroxide solution under ice-cooling conditions, stir, and then add 1g of 2,4-dimethoxymethoxy-6-hydroxyacet...

Embodiment 2

[0036] Embodiment 2: 2-(3 / Anti-inflammatory activity of -pyridyl)-3,5,7-trihydroxychroman-4-one (a)

[0037] (1) Establishment of inflammation model

[0038] Take the cultured cells in the logarithmic growth phase, digest with trypsin, and take 1% fetal bovine serum H-DMEM medium to make 8×10 4 cells / ml single cell suspension, uniformly inoculated in 96-well plate with 100 μl per well, placed at 37°C, 5% CO 2 Culture in an incubator, and discard the old medium after 12 hours. The complete medium containing LPS (1 μg / mL) was added, and the culture was continued for 24 hours, and the establishment of the cell inflammation model was completed.

[0039] (2) ELISA was used to detect the levels of inflammatory factors IL-1β, IL-6 and TNF-ɑ in the culture medium of RAW264.7 cells induced by LPS

[0040] Take the cultured cells in the logarithmic growth phase, digest with trypsin, and take 1% fetal bovine serum H-DMEM medium to make 8×10 4 cells / ml single cell suspension, unifo...

Embodiment 3

[0045] Embodiment 3: 2-(2 / Total Synthesis of -furyl)-3,5,7-trihydroxychroman-4-one

[0046] (1) Preparation of 2,4-dimethoxymethoxy-6-hydroxyacetophenone

[0047]

[0048] Dissolve 1g of 2,4,6-trihydroxyacetophenone in 30ml of acetone, add 2.88g of anhydrous potassium carbonate, reflux and stir for 30min, cool slightly, add 1.13ml of chloromethyl ether dropwise, continue to reflux, TLC plate detects the reaction After completion, the reaction was quenched by adding water, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and rotary evaporated to obtain 1.32 g of 2,4-dimethoxymethoxy-6-hydroxyacetophenone with a yield of 86.62%.

[0049] (2) 2-furyl-2 / ,4 / -Dimethoxymethoxy-6 / - Preparation of hydroxychalcone

[0050]

[0051] Dissolve 0.70g of 2-furfuraldehyde in 25mL of anhydrous methanol, add 5.20mL of 50% sodium hydroxide solution under ice-cooling conditions, stir, and then add 1g of 2,4-dimethoxymethoxy-6-hydroxyphenylethyl k...

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PUM

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Abstract

The invention discloses a flavanonol compound containing N aromatic heterocycte, which has a following structure in a specification, wherein an Ar substituent in a formula I is shown as one in the specification, and the substituted position of the compound comprises all the substituted positions on the N aromatic heterocycte. The novel flavanonol compound containing N aromatic heterocycte has strong anti-inflammatory activity, and compared with positive contrast indomethacin and taxifolin, the activity is equal or better. The flavanonol compound can be used for preparing the anti-inflammatorymedicines.

Description

technical field [0001] The invention relates to a dihydroflavonol compound containing an N aromatic heterocycle, a preparation method thereof and an application thereof in preparation of anti-inflammatory drugs. Background technique [0002] Inflammatory response is a defense response produced by the body in response to internal and external stimuli, and is usually manifested clinically as signs of redness, swelling, heat pain, and dysfunction. In most cases, inflammation is beneficial, which is the body's automatic defense response. In the process of inflammation, on the one hand, inflammatory factors will directly or indirectly cause damage to human tissues and cells; on the other hand, due to inflammatory hyperemia and exudative reactions, the damage factors are diluted, killed and surrounded; Damaged tissue is regenerated and healed. Therefore, it can be said that inflammation is a unified process of injury and anti-injury. Anti-inflammatory drugs currently used clini...

Claims

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Application Information

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IPC IPC(8): C07D405/04C07D407/04A61P29/00
Inventor 叶晓川胡春玲周宗宝王红刘焱文
Owner HUBEI UNIV OF CHINESE MEDICINE
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