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A kind of quercetin derivative and its preparation method and application

A derivative, quercetin technology, applied in the field of pharmaceutical preparation, can solve the problems of low bioavailability, large intermolecular attraction, poor water solubility of quercetin, etc., and achieves simple synthesis process requirements and strong acetylcholinesterase inhibitory activity. , the effect of easy operation

Active Publication Date: 2021-05-25
JIANGSU MARINE RESOURCES DEV RES INST LIAN YUNGANG +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because quercetin is a planar molecule, the molecular packing is relatively tight, the intermolecular attraction is relatively large, and it is not easy to be dispersed by solvent or solute, so the water solubility of quercetin is poor and the bioavailability is low, which makes the clinical application of quercetin difficult. Applications are extremely limited

Method used

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  • A kind of quercetin derivative and its preparation method and application
  • A kind of quercetin derivative and its preparation method and application
  • A kind of quercetin derivative and its preparation method and application

Examples

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Embodiment 1

[0026] A kind of quercetin derivative of the present invention, its chemical structural formula has formula (I) shown in:

[0027]

[0028] The chemical name is 2-(3,4-dihydroxyphenyl)-3-(5-N,N-diethylaminopentyloxy)-5,7-dihydroxy-4H-1-benzopyran-4 -ketone.

[0029] The preparation method of quercetin derivative of the present invention comprises the following steps:

[0030] (1) Preparation of 7,3',4'-tribenzyloxyquercetin; dry rutin dehydrated from crystallization water was dissolved in anhydrous DMF, then added anhydrous potassium carbonate and stirred at room temperature for 15 minutes, then Add benzyl bromide and stir at 53°C for 4 hours. After the reaction, use 10% acetic acid to adjust the pH value to 6.5, filter to obtain a precipitate, dissolve the precipitate in absolute ethanol, add concentrated hydrochloric acid, and reflux the mixture at 78°C for 2 hours. hours, cooled to room temperature and filtered to obtain a light yellow solid, which was recrystallized f...

Embodiment 2

[0039] The difference between embodiment 2 and embodiment 1 is:

[0040] The preparation method of quercetin derivative of the present invention comprises the following steps:

[0041] (1) Preparation of 7,3',4'-tribenzyloxyquercetin; dry rutin dehydrated from crystallization water was dissolved in anhydrous DMF, then added anhydrous potassium carbonate and stirred at room temperature for 15 minutes, then Add benzyl bromide and stir at 50°C for 3 hours. After the reaction, use 10% acetic acid to adjust the pH value to 6, filter to obtain a precipitate, dissolve the precipitate in absolute ethanol, add concentrated hydrochloric acid, and reflux the mixture at 78°C for 2.5 hours, cooled to room temperature and filtered to obtain a light yellow solid, which was recrystallized from dichloromethane / methanol to obtain 7,3',4'-tribenzyloxyquercetin. The mass ratio of described rutin, anhydrous potassium carbonate is 34:53.79, and the mass volume ratio of described rutin and benzyl b...

Embodiment 3

[0045] The difference between embodiment 3 and embodiment 1 is:

[0046] The preparation method of quercetin derivative of the present invention comprises the following steps:

[0047] (1) Preparation of 7,3',4'-tribenzyloxyquercetin; dry rutin dehydrated from crystallization water was dissolved in anhydrous DMF, then added anhydrous potassium carbonate and stirred at room temperature for 15 minutes, then Add benzyl bromide and stir at 55°C for 3.5 hours. After the reaction, use 10% acetic acid to adjust the pH value to 6.3, filter to obtain a precipitate, dissolve the precipitate in absolute ethanol, add concentrated hydrochloric acid, and reflux the mixture at 78°C for 2.3 hours, cooled to room temperature and filtered to obtain a light yellow solid, which was recrystallized from dichloromethane / methanol to obtain 7,3',4'-tribenzyloxyquercetin. The volume ratio of the anhydrous DMF, absolute ethanol and concentrated hydrochloric acid is 38:78:15.

[0048] (2) 2-(3,4-dibenz...

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Abstract

The invention discloses a quercetin derivative, a preparation method and application thereof. A kind of quercetin derivative of the present invention, its chemical structural formula has formula (I): chemical name is 2-(3,4-dihydroxyphenyl)-3-(5-N, N-diethyl Amyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one. 2-(3,4-dihydroxyphenyl)-3-(5-N, N-diethylaminopentyloxy)-5,7-dihydroxy-phenyl obtained by chemically modifying quercetin in the present invention The 4H-1-benzopyran-4-one has acetylcholinesterase inhibitory activity and can be used for preparing functional food or medicine against Alzheimer's disease.

Description

technical field [0001] The invention relates to the field of medicine preparation, in particular to a quercetin derivative and its preparation method and application. Background technique [0002] Alzheimer's disease is a degenerative disease of the brain that is common in the elderly. With high morbidity and high mortality, the disease has become one of the most threatening diseases in modern society. The pathogenesis of Alzheimer's disease is still unclear. In recent years, scientists have proposed a variety of etiological hypotheses from different angles for the etiology, pathology and related molecular biology research of Alzheimer's disease. Among them, the representative Hypotheses include cholinergic theory, toxic effects of β-amyloid protein, free radical oxidative damage, inflammatory lesions, brain energy metabolism disorders, gene defects and mutations, and so on. [0003] The cholinergic theory believes that the brain cholinergic nervous system of patients with...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/62A61P25/28A23L33/10
CPCA23V2002/00A23L33/10C07D311/62A23V2200/322
Inventor 刘玉委史大华唐总明朱荟龙马晓冬宋晓凯刘玮炜宋梦秋
Owner JIANGSU MARINE RESOURCES DEV RES INST LIAN YUNGANG
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