4-substituted-2-arylvinyl quinoline derivative, and preparation method and application thereof

A technology of arylvinylquinoline and its derivatives, which is applied in drug combinations, active ingredients of heterocyclic compounds, muscular system diseases, etc., can solve the problems of complex pathogenesis and mutual influence of Alzheimer's disease, and achieve simple preparation methods , good Aβ aggregation, easy synthesis effect

Inactive Publication Date: 2014-10-22
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] From the above, it can be known that the pathogenesis of Alzheimer's disease is complex and interacts with each other.

Method used

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  • 4-substituted-2-arylvinyl quinoline derivative, and preparation method and application thereof
  • 4-substituted-2-arylvinyl quinoline derivative, and preparation method and application thereof
  • 4-substituted-2-arylvinyl quinoline derivative, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: the synthesis of 4-methylpiperazinyl-2-methylquinoline (compound 3a)

[0035] Put 5g of 4-chloro-2-methylquinoline in a 50mL single-necked bottle, add 20mL of methylpiperazine and 0.6g of p-toluenesulfonic acid in sequence, heat to reflux, TLC traces that the reaction is complete (about 10h), after cooling Add 50mL of water, adjust the pH value to be alkaline with aqueous sodium hydroxide solution, extract three times with 50ml, 50ml, and 50ml of dichloromethane, combine the organic phases, wash once with 40mL of water, spin dry the organic layer, and dichloromethane / methanol (volume Purification by silica gel chromatography (ratio 100 / 1) as eluent afforded 3a 5.1 g as a pale yellow oil. Yield 75%; 1 H NMR (400MHz, CDCl 3 )δ7.98(t, J=8Hz, 2H), 7.62(t, J=8Hz, 1H), 7.42(t, J=8Hz, 1H), 6.74(s, 1H), 3.27(s, 4H), 2.73(s,4H),2.69(s,3H),2.43(s,3H).

[0036]

Embodiment 2

[0037] Embodiment 2: the synthesis of compound 3b

[0038] The synthesis method is the same as in Example 1; the difference is that piperidine is used instead of methylpiperazine, and dichloromethane / petroleum ether (volume ratio 1 / 1) is purified by silica gel chromatography as an eluent to obtain a light yellow oil 3b. The yield is 72%; 1 H NMR (400MHz, CDCl 3 )δ7.95(d,2H),7.59(t,J=8Hz,1H),7.40(t,J=8Hz,1H),6.71(s,1H),3.15(s,1H),2.68(d, J=9.9Hz,3H),1.84(s,1H).

[0039]

Embodiment 3

[0040] Embodiment 3: the synthesis of compound 3c

[0041] The synthesis method was the same as in Example 1; the difference was that p-methoxyaniline was used instead of methylpiperazine, and the obtained crude product was recrystallized from ethanol to obtain 3c as a white solid. The yield is 82.1%; 1 H NMR (400MHz, CDCl 3 ): δ7.97(d, J=8.4Hz, 1H), 7.86(d, J=8.3Hz, 1H), 7.65(t, J=7.6Hz, 1H), 7.44(t, J=7.6Hz, 1H ),7.24(d,J=8.9Hz,2H),6.98(d,J=8.8Hz,2H),6.59(s,1H),6.51(s,1H),3.86(s,3H),2.54(s ,3H).

[0042]

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Abstract

The invention discloses a 4-substituted-2-arylvinyl quinoline derivative, and a preparation method and an application thereof. A structural formula of the derivative is shown as the formula (I). The formula (I) is shown in the description. In the formula (I), R represents hydrogen, cyclic amino fatty amino, aromatic amino or substituted aromatic amino; and Ar represents substituted carbazole-3-yl, substituted phenyl, phenyl, indole-3-yl or 7-diethylin-2-oxo-1-benzopyran-3-yl. The invention also discloses the preparation method and application of the 4-substituted-2-arylvinyl quinoline derivative. The derivative provided by the invention has the advantages of A[beta] aggregation resistance, activity for resisting oxidation, activity for resisting butylcholinesterase, and metal complexation capacity, and has wide application space in preparing drugs for resisting Alzheimer's diseases.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, more specifically, to a 4-substituted-2-arylvinylquinoline derivative, a preparation method and application thereof. Background technique [0002] Alzheimer's disease (AD), also known as senile dementia, is a chronic, progressive degenerative disease of the central nervous system. Its pathological features are diffuse brain atrophy, characteristic neurofibrillary tangles, senile plaque deposition in brain tissue, and cerebral arterial amyloidosis. In recent years, with the aging of the world's population, the incidence of Alzheimer's disease has been increasing year by year, and it has become one of the major diseases that seriously threaten the health and quality of life of the elderly. [0003] So far, there are four main hypotheses about the pathogenesis of Alzheimer's disease: 1. The amyloid cascade hypothesis, which involves designing and synthesizing small molecule ligands that can inhib...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/42C07D215/44C07D401/06C07D215/14C07D215/12C07D405/06A61K31/496A61K31/4709A61K31/4706A61K31/5377A61K31/47A61P25/28A61P21/04A61P39/06
CPCC07D401/06C07D215/12C07D215/14C07D215/42C07D215/44C07D405/06
Inventor 黄志纾古练权王晓琴夏春丽黄世亮谭嘉恒欧田苗
Owner SUN YAT SEN UNIV
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