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A kind of naringenin-o-alkylamine compound, preparation method and application

A technology of naringenin and alkylamine, which is applied in the directions of active ingredients of heterocyclic compounds, drug combinations, organic chemistry, etc., can solve the problems of poor long-term curative effect, single action target, and many toxic and side effects in AD patients, and achieve obvious results. Neuroprotective function, strong complexation, the effect of improving motor function

Inactive Publication Date: 2020-07-31
NANYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such as: cholinesterase inhibitors and N-methyl-D-aspartate receptor antagonists, etc., but these drugs have a single target
There are many toxic and side effects in clinical use, and the long-term curative effect on AD patients is not good.

Method used

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  • A kind of naringenin-o-alkylamine compound, preparation method and application
  • A kind of naringenin-o-alkylamine compound, preparation method and application
  • A kind of naringenin-o-alkylamine compound, preparation method and application

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Embodiment 1

[0041] The general chemical structure formula of the naringenin-O-alkylamine compound of the embodiment of the present invention 1-128 is as follows:

[0042]

[0043] Among them, n, R 1 , R 2 See Table 1.

[0044] Table 1 The naringenin-O-alkylamine compounds of Examples 1-128 of the present invention

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053] I-43: Light yellow oil, 50.6% yield, 98.2% HPLC purity. 1 H NMR (400 MHz, CDCl 3 )δ12.02(s,1H,OH),7.52(d,J=8.0 Hz,1H,Ar-H),7.48(d,J=7.2 Hz,1H,Ar-H),7.36(d,J= 8.4 Hz, 2H, 2×Ar-H), 7.31-7.24(m, 2H, 2×Ar-H), 6.96(t, J=7.6 Hz, 2H, 2×Ar-H), 6.91(d, J =8.8 Hz, 2H, 2×Ar-H), 6.89(d, J=3.2 Hz, 1H, Ar-H), 6.87(d, J=3.2Hz, 1H, Ar-H), 6.01(dd, J 1 = 6.4 Hz,J 2 =2.4 Hz, 2H, 2×Ar-H), 5.36(dd, J 1 =10.0 Hz,J 2 =2.8 Hz,1H,Ar-H),3.99-3.93(m,4H,2×OCH 2 ),3.87(s,2H,phCH 2 ),3.84(s,3H,OCH 3 ),3.83(s,3H,OCH 3 ),3.81(s,2H,phCH 2 ),3.09(dd,J 1 =13.2 Hz,J 2 = 4.0 Hz, 1H, 1 / 2 COCH ...

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Abstract

The invention discloses a naringenin-O-alkyl amine compound, a preparation method and application. A chemical structural general formula of the naringenin-O-alkyl amine compound is as shown in a formula (I). The preparation method comprises the following steps: reacting in a first solvent and under a first alkaline condition by taking naringenin and dibromo alkane Br(CH2)nBr as raw materials, thusobtaining corresponding 2,7-dibromo alkoxy naringenin; then enabling the 2,7-dibromo alkoxy naringenin to react with different secondary amines NR1R2 in a second solvent and under a second alkaline condition, thus obtaining a target compound-the naringenin-O-alkyl amine compound. The naringenin-O-alkyl amine compound disclosed by the invention has multi-target action, and can be widely used for preventing or treating neurodegenerative diseases.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and specifically relates to a naringenin-O-alkylamine compound, a preparation method and an application. Background technique [0002] Alzheimer's disease (Alzheimer's disease, AD, senile dementia) is a central nervous system degenerative disease mainly characterized by progressive cognitive impairment and memory impairment. With the rapid aging of the global population, the elderly population Health problems have become a major social problem that needs to be solved urgently. Alzheimer's disease (AD) is one of the diseases with the highest morbidity and mortality among the elderly. According to the "2015 Global Alzheimer's Report" released by Alzheimer's Disease International (ADI), more than 46 million people worldwide suffered from dementia in 2015, and it is predicted that by 2050, the global There will be 131.5 million people suffering from dementia, and the incidence rate of d...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/32C07D405/14C07D519/00A61K31/353A61K31/438A61K31/496A61K31/4545A61K31/5377A61K31/4725A61K31/55A61P25/00A61P25/28A61P25/16A61P25/14A61P25/04A61P27/06A61P9/10A61P31/18
Inventor 桑志培王柯人柳文敏时健于林涛程新锋刘青妹
Owner NANYANG NORMAL UNIV
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