4-flexible amine-2-aryl vinyl quinoline derivative, preparation method and applications thereof

An arylvinylquinoline and flexible amine group technology, which is applied in the field of 4-flexible amino-2-arylvinylquinoline derivatives and their preparation, can solve problems such as unsatisfactory drug treatment effect, and achieve inhibition of Effect of antioxidant capacity, low cytotoxicity, good metal complexation capacity

Active Publication Date: 2017-11-10
GUANGDONG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the effect of drug therapy

Method used

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  • 4-flexible amine-2-aryl vinyl quinoline derivative, preparation method and applications thereof
  • 4-flexible amine-2-aryl vinyl quinoline derivative, preparation method and applications thereof
  • 4-flexible amine-2-aryl vinyl quinoline derivative, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Synthesis of 4-(3-diethylamino)-propylamino-2-methylquinoline (compound 2a)

[0039] Put 1.77g of 4-chloro-2-methylquinoline, 10mL of 3-diethylaminopropylamine, and 0.6g of p-toluenesulfonic acid into a 20mL microwave reaction tube and heat the reaction with microwave for 0.5h, followed by TLC until the reaction is complete. Cool, add 50mL of water, and use aqueous sodium hydroxide to adjust the pH to be alkaline, extract with dichloromethane (50mL×3), combine the organic layers, wash once with 40mL of water, spin dry, and dichloromethane / methanol (volume ratio 50 / 1) was purified by silica gel chromatography as eluent to obtain pale yellow oil 2a; yield 66%. 1 H NMR (400MHz, CDCl 3 ): δ7.90(d, J=8.3Hz, 1H), 7.78(s, 1H), 7.71(d, J=8.4Hz, 1H), 7.57(t, J=8.3Hz, 1H), 7.32(t ,J=8.2Hz,1H),6.23(s,1H),3.39(q,J=10.1Hz,2H),2.68(t,J=8.3Hz,2H),2.64(q,J=16Hz,4H) ,2.61(s,3H),1.91(m,2H),1.10(t,J=7.1Hz,6H).

[0040]

Embodiment 2

[0041] Embodiment 2: the synthesis of compound 2b

[0042] The synthesis method was the same as in Example 1; the difference was that 3-dimethylaminopropylamine was used instead of 3-diethylaminopropylamine, and purified by silica gel chromatography to obtain light yellow oil 2b; the yield was 64%. 1 H NMR (400MHz, CDCl 3 ): δ7.89(d, J=7.8Hz, 1H), 7.64(d, J=7.7Hz, 1H), 7.53(s, 1H), 7.43(s, 1H), 7.30(s, 1H), 6.20 (s,1H),3.31(s,2H),2.59(s,3H),2.47(s,2H),2.30(s,6H),1.84(s,2H).

[0043]

Embodiment 3

[0044] Embodiment 3: the synthesis of compound 2c

[0045] The synthesis method was the same as in Example 1; the difference was that 2-dimethylaminoethylamine was used instead of 3-diethylaminopropylamine, and the obtained crude product was purified by silica gel chromatography to obtain light yellow liquid 2c; the yield was 67%. 1 H NMR (400MHz, CDCl 3 ): δ7.90(d, J=8.3Hz, 1H), 7.76(d, J=8.3Hz, 1H), 7.58(t, J=8.3Hz, 1H), 7.35(t, J=8.3Hz, 1H ),6.28(s,1H),5.84(s,1H),3.28(dd,J=11.3,4.9Hz,2H),2.66(t,J=6.9Hz,2H),2.61(s,3H),2.29 (s,6H).

[0046]

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Abstract

The invention belongs to the field of medicine and chemical industry, and specifically discloses a 4-flexible amine-2-aryl vinyl quinoline derivative and a preparation method thereof, and applications of the 4-flexible amine-2-aryl vinyl quinoline derivative in preparation of anti-Alzheimer disease drugs, wherein the chemical formula of the 4-flexible amine-2-aryl vinyl quinoline derivative is defined in the specification. The invention further discloses the preparation method and the uses of the 4-flexible amine-2-aryl vinyl quinoline derivative. According to the present invention, the 4-flexible amine-2-aryl vinyl quinoline derivative has advantages of monoamine oxidase-B activity inhibiting, A[beta] aggregation resistance, anti-oxidation activity, metal complexing, low biological toxicity and good safety, such that the 4-flexible amine-2-aryl vinyl quinoline derivative has broad application space in the preparation of anti-Alzheimer disease drugs.

Description

technical field [0001] The invention relates to the technical fields of medicine and chemical industry, and more specifically, to a 4-flexible amino-2-arylvinylquinoline derivative and its preparation method and application. Background technique [0002] Alzheimer's disease (AD), also known as senile dementia, is a chronic, progressive degenerative disease of the central nervous system. In recent years, with the development of society and the improvement of people's living standards, the world's population is aging, so the incidence of AD is increasing year by year, and it has become one of the main diseases that seriously threaten the health and quality of life of the elderly. Studies have shown that the pathological features of AD mainly include senile plaques (senile plaques, AP) with β-amyloid aggregation outside the brain nerve cells, and neurofibrillary tangles formed by the aggregation of abnormally phosphorylated tau protein in the neuron cytoplasm. , and neuronal d...

Claims

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Application Information

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IPC IPC(8): C07D215/46C07D401/06C07D215/42A61P25/28A61P21/04A61P9/00A61P39/06
CPCC07D215/42C07D215/46C07D401/06
Inventor 王晓琴谢晓阳陈嘉和钟志乾蔡远鸿何明华
Owner GUANGDONG MEDICAL UNIV
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