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Arylethanolamine quercetin derivative as well as preparation method and application thereof

A technology of ethanolamine quercetin and derivatives, applied in the field of medicine, can solve the problems of slow onset of glucocorticoids and the like

Inactive Publication Date: 2017-05-10
SHIJIAZHUANG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The current treatment of asthma has shifted from relieving bronchial smooth muscle spasm to controlling airway inflammation and airway hyperresponsiveness. However, due to the slow onset of glucocorticoids, it can quickly relieve the β-β effect of bronchial smooth muscle spasm during the acute attack of asthma. 2 AR agonists are also essential for effective therapeutics

Method used

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  • Arylethanolamine quercetin derivative as well as preparation method and application thereof
  • Arylethanolamine quercetin derivative as well as preparation method and application thereof
  • Arylethanolamine quercetin derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Preparation of arylethanolamine quercetin derivative (1) and its hydrochloride

[0021] Add 122 mg (1.5 mmol) of formaldehyde solution, 175 mg (1.5 mmol) of concentrated ammonia water, 302 mg (1 mmol) of quercetin and 5 mL of ethanol into a closed pressure-resistant reactor, add 3 drops of hydrochloric acid, and heat to 75- React at 80°C for 3 hours, cool naturally, precipitate a solid, filter with suction, and separate the crude product by chromatography (V (n-butanol): V (water): V (HOAc) = 4:1:1, eluted with methanol to obtain intermediate 105 mg of solid Mannich base light yellow solid, yield 31.7%. m.p.>300℃; 1 H NMR (400 MHz, DMSO-d 6 )δ: 7.74(d, 1H), 7.60 (d, 1H), 6.92 (d, 1H), 6.19 (s, 1H), 3.86 (s, 2H).

[0022] N 2 Under protection, 331 mg (1.0 mmol) of the intermediate Mannich base and 182.4 mg (1.2 mmol) of 3,4-dihydroxyphenyloxirane were added to 5 mL of DMF, stirred at room temperature for 3 days, the solvent was evaporated under reduced pressure, and 1...

Embodiment 2

[0026] Preparation of arylethanolamine quercetin derivative (2) and its L-(+)-tartrate

[0027] Replace 182.4 mg (1.2 mmol) of 3,4-dihydroxyphenyl oxirane in Example 1 with 244.8 mg (1.2 mmol) 3,5-dichloro-4-aminophenyl oxirane, other same Example 1, 317.6 mg of compound (2) was obtained with a yield of 61.2%. MS(ESI)[M+H] + = 519.0,[M-H] - = 517.0.

[0028] Preparation of arylethanolamine quercetin derivative (2) L-(+)-tartrate

[0029] N 2 Under protection, add 518 mg (1.0 mmol) of compound (2) into 5 mL of absolute ethanol, heat to dissolve, add 65 mg (1.1 mmol) of L-(+)-tartaric acid aqueous solution 5 mL, react at 40-45 ° C for 4 h, cool to room temperature , filtered, washed with 95% ethanol, and dried to obtain 607.8 mg of compound (2) L-(+)-tartrate, with a yield of 91%.

Embodiment 3

[0031] Preparation of arylethanolamine quercetin derivative (3) and its fumarate

[0032] Replace 182.4 mg (1.2 mmol) of 3,4-dihydroxyphenyl oxirane in Example 1 with 285.1 mg (1.2 mmol) 3-trifluoromethyl-4-amino-5-chlorophenyl oxirane alkane, and the others were the same as in Example 1 to obtain 348.2 mg of compound (3), with a yield of 63.0%. MS(ESI)[M+H] + = 553.0,[M-H] - = 551.0.

[0033] Preparation of arylethanolamine quercetin derivative (3) fumarate

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Abstract

The invention relates to arylethanolamine quercetin derivatives or pharmaceutically acceptable salts thereof. The derivatives comprise stereoisomers or tautomers thereof. The method for preparing the derivatives comprises the following steps: preparing Mannich base of quercetin from quercetin, formaldehyde and ammonia, and reacting with aryl ethylene oxide, thereby obtaining the arylethanolamine quercetin derivative. The arylethanolamine quercetin derivatives have the effects of treating asthma.

Description

technical field [0001] The invention relates to arylethanolamine quercetin derivatives and their application in pharmacy, belonging to the technical field of medicine. Background technique [0002] Bronchial asthma (abbreviated as asthma) is the most common chronic airway inflammatory disease. In recent years, the incidence rate is increasing day by day. There are about 150-200 million patients in the world, and 180,000 people die from asthma every year. The number of cases has increased more than three times in the past 10 years. The prevention and treatment of asthma has become a major topic of common concern to scholars from all over the world. [0003] The current treatment of asthma has shifted from relieving bronchial smooth muscle spasm to controlling airway inflammation and airway hyperresponsiveness. However, due to the slow onset of glucocorticoids, it can quickly relieve the β-β effect of bronchial smooth muscle spasm during the acute attack of asthma. 2 AR agon...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30A61P11/06
CPCC07D311/30
Inventor 张宝华刘斯婕史兰香
Owner SHIJIAZHUANG UNIVERSITY
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