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A kind of polyhydroxychalcone compound and its application

A technology of polyhydroxychalcone and methylchalcone, which is applied in the field of medicinal chemistry, can solve problems such as the increase of Aβ protein, achieve a good inhibitory effect, and inhibit the effect of cell ferroptosis

Active Publication Date: 2020-11-13
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, some studies have shown that the increase of lipid peroxidation will lead to the increase of Aβ protein by up-regulating β-secretase

Method used

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  • A kind of polyhydroxychalcone compound and its application
  • A kind of polyhydroxychalcone compound and its application
  • A kind of polyhydroxychalcone compound and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]

[0030] Preparation of (E)-3'-hydroxy-3-methylchalcone (6a)

[0031] Add 1.36g (0.01mol) 3-hydroxyacetophenone, 20mL ethanol and 10mL KOH (10%) aqueous solution in a 50mL three-necked flask, stir at room temperature to make it fully dissolve, then add 1.2g (0.01mol) 3 -Methylbenzaldehyde, stirred at room temperature for 24h. After the completion of the reaction was monitored, 10% HCl was added dropwise to acidify to PH = 6, extracted three times with 30 mL ethyl acetate, combined, and then washed with 20 mL saturated brine, the ethyl acetate phase was concentrated by rotary evaporation, and dried to obtain a yellow solid. After column chromatography (200-400 mesh silica gel), 1.77 g of yellow powder solid (6a) was obtained, with a yield of 74.2%.

[0032] After testing, 1 H NMR is: 1 H NMR (700MHz, CDCl 3 )7.82(d, J=15.7Hz, 1H), 7.72(dd, J=2.3, 1.7Hz, 1H), 7.59(d, J=7.7Hz, 1H), 7.52(d, J=15.7Hz, 1H) , 7.44(s,1H),7.43(d,J=7.7Hz,1H),7.39(t,J=7.9Hz,1H),7.31(t,J=7....

Embodiment 2

[0037]

[0038] Preparation of (E)-3'-hydroxy-3,4-dimethoxychalcone (6b)

[0039] Add 1.36g (0.01mol) of 3-hydroxyacetophenone, 20mL of ethanol and 10mL of KOH (10%) in a 50mL three-necked flask, stir at room temperature to fully dissolve, then add 1.66g (0.01mol) of 3 , 4-dimethoxybenzaldehyde, stirred at room temperature for 24h. After the completion of the reaction was monitored, 10% HCl was added dropwise to acidify to PH = 6, extracted three times with 30 mL ethyl acetate, combined, and then washed with 20 mL saturated brine, the ethyl acetate phase was concentrated by rotary evaporation, and dried to obtain a yellow solid. After column chromatography (200-400 mesh silica gel), 1.76 g of yellow powder solid (6b) was obtained, with a yield of 61.9%.

[0040] After testing, 1 H NMR is: 1 H NMR (700MHz, CDCl 3 )δ7.75(d, J=15.6Hz, 1H), 7.67(dd, J=8.4, 1.8Hz, 1H), 7.61(d, J=1.8Hz, 1H), 7.51(d, J=15.6Hz, 1H), 7.27(d, J=5.8Hz, 1H), 7.19(d, J=7.7Hz, 1H), 7.16(s, 1H), 6.94(d...

Embodiment 3

[0045]

[0046] Preparation of (E)-3',5'-dihydroxy-3-methylchalcone (10a)

[0047] 1) Step 1: Synthesis of 3-hydroxy-5-methoxymethoxyacetophenone

[0048] Add 1.52g (0.01mol) of 3,5-dihydroxyacetophenone, 30mL of anhydrous acetone and 2.76g (0.02mol) of anhydrous potassium carbonate into a 50mL three-necked flask, stir in an ice bath for 30min, then slowly add 4mL (0.05 mol) bromomethyl methyl ether and 5mL of acetone mixed solution, reflux reaction for 4h. After the reaction was complete as monitored by TLC, the mixture was cooled to room temperature and impurities were filtered. After the solvent was evaporated to dryness by rotary evaporation, 1.58 g of oily liquid was obtained by silica gel column chromatography, with a yield of 65.8%.

[0049] 2) Step 2: Synthesis of (E)-3'-hydroxy-5'-methoxymethoxy-3-methylchalcone

[0050] Add 2.40g (0.01mol) of 3-hydroxy-5-methoxymethoxyacetophenone, 20mL of ethanol and 10mL of KOH (10%) aqueous solution in a 50mL three-necked fla...

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Abstract

The invention provides a polyhydroxy chalcone compound and application thereof. The compound has a good inhibiting effect on aggregation of Abeta protein, and can eliminate or reduce toxicity caused by Abeta protein aggregation effectively in a cell experiment. Meanwhile, the compound can be used as a free-radical peroxidation inhibitor, and then can inhibit ferroptosis so that the compound can beused for treating alzheimer''s disease or used as the free-radical peroxidation inhibitor, or the like.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a polyhydroxychalcone compound and its application. Background technique [0002] Alzheimer's disease (AD) is a progressive neurodegenerative disease, and its main pathological features are memory impairment, language confusion, severe behavioral abnormalities, and learning deficits. In 2013, the International Alzheimer's Association released a report, according to statistics, there are about 44 million AD patients in the world, and by 2050, the number of patients is expected to increase to 135 million. At present, there are only 5 drugs approved for the treatment of Alzheimer's disease, 4 of which are all acting on acetylcholinesterase or butyrylcholinesterase, namely tacrine, donepezil, rivastigmine and Galantamine. The other is memantine, whose target is the N-methyl-D-aspartate receptor. The above-mentioned drugs can alleviate the symptoms of AD patients, but they cannot...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/835C07C49/84A61P25/28A61P39/06
CPCA61P25/28A61P39/06C07C49/835C07C49/84
Inventor 戴荣继丛林李博邓玉林
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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