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Quinoline tryptamine hybrid and its application in the preparation of drugs for the treatment of Alzheimer's disease

A drug and pharmaceutical technology, applied in the field of medicine, can solve problems such as complicated pathogenesis, no breakthrough progress, and no new drugs successfully marketed.

Inactive Publication Date: 2021-11-16
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, the development of anti-AD drugs aimed at inhibiting Aβ aggregation or clearing senile plaques formed by Aβ aggregation, or targeting other single targets, has been a hot spot in this field, but so far, no breakthroughs have been made. No new drug successfully marketed
[0004] In view of the complex pathogenesis of AD, the etiological mechanism has not been fully elucidated, and the various mechanisms are interconnected and affect each other, which brings great difficulties to the treatment of the disease.

Method used

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  • Quinoline tryptamine hybrid and its application in the preparation of drugs for the treatment of Alzheimer's disease
  • Quinoline tryptamine hybrid and its application in the preparation of drugs for the treatment of Alzheimer's disease
  • Quinoline tryptamine hybrid and its application in the preparation of drugs for the treatment of Alzheimer's disease

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] The synthesis of embodiment 1 8-hydroxyquinoline-2-formaldehyde

[0078]

[0079] SeO 2 (2.22g, 20mmol) was added to 1,4-dioxane solution (50mL), and an aqueous solution (0.7mL) was added, heated to 60°C so that SeO 2 After complete dissolution, a solution of 2-methyl-8-hydroxyquinoline (1.59 g, 10 mmol) in 1,4-dioxane (10 mL) was added dropwise within half an hour. Heat to reflux until the reaction is complete. Suction filtration, vacuum drying, and purification by column chromatography yielded 1.48 g of a pale yellow solid. Yield 86%.

[0080] 1 H NMR (400MHz, (CD 3 ) 2CO)δ10.16(s,1H),9.22(s,1H),8.55(d,J=8.5Hz,1H),8.04(d,J=8.5Hz,1H),7.69(t,J=8.0Hz ,1H),7.57(dd,J=8.2,0.9Hz,1H),7.28(dd,J=7.7,1.0Hz,1H).

Embodiment 2

[0081] Example 2 8-hydroxyquinoline-2-carboxylic acid

[0082]

[0083] SeO 2 (2.22g, 20mmol) was added into pyridine (20mL), and after heating to 60°C, 2-methyl-8-hydroxyquinoline (3.18g, 20mmol) was added. After the addition is complete, stir at 120°C until the reaction is complete. After vacuum-filtering, it was dissolved in aqueous KOH (10%) and the residual solid was filtered off. The filtered liquid was acidified with aqueous hydrochloric acid (10%). After suction filtration, 1.891 g of red solid was obtained. Yield 50%.

[0084] 1 H NMR (400MHz, (CD 3 ) 2 CO)δ9.68(s,1H),8.63(d,J=8.5Hz,1H),8.27(d,J=8.5Hz,1H),7.70(t,J=7.9Hz,1H),7.60(d ,J=8.2Hz,1H),7.28(d,J=7.6Hz,1H).

Embodiment 3

[0085] Example 3 5-(chloromethyl)quinolin-8-ol hydrochloride

[0086]

[0087] 8-Hydroxyquinoline (5.84 g, 40.2 mmol) was added to 70 mL of concentrated hydrochloric acid, and 6.4 mL of formaldehyde (37%) solution was added along with a catalytic amount of zinc chloride (0.6 g). After stirring overnight at room temperature, the mixture was filtered, washed with copious amounts of acetone and dried. 7.86 g of a yellow solid was obtained with a yield of 85%.

[0088] 1 H NMR (400MHz, DMSO-d 6 )δ9.22(d, J=7.9Hz, 1H), 9.13(dd, J=5.0, 1.1Hz, 1H), 8.12(dd, J=8.6, 5.1Hz, 1H), 7.87(d, J=8.0 Hz,1H),7.51(d,J=8.0Hz,1H),5.33(s,2H).

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Abstract

The invention belongs to the technical field of medicine, and in particular relates to a quinoline tryptamine hybrid and its application in the preparation of medicines for treating and / or preventing Alzheimer's disease. Specifically disclosed are compounds represented by formula (I) and pharmaceutically acceptable salts thereof. The quinoline tryptamine hybrid compound of the present invention has excellent ability to scavenge oxygen free radicals, protect SH-SY5Y cell oxidative damage induced by hydrogen peroxide, good passive dialysis ability of blood-brain barrier, and inhibit Aβ self-aggregation It is a multi-target anti-Alzheimer's disease active molecule; it is expected to be used as a clinical drug for treating and / or preventing Alzheimer's disease.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a quinoline tryptamine hybrid and its application in the preparation of medicines for treating and / or preventing Alzheimer's disease. Background technique [0002] Alzheimer's Disease (AD), also known as Alzheimer's disease, is an age-related degenerative disease of the central nervous system. The disease was first discovered by German psychiatrist Alois Alzheimer in 1906, more than 100 years ago. The research results show that the neuropathological features of AD are mainly neurofibrillary tangles (neurofibrillary tangles, NFTs) in nerve cells formed by abnormal aggregation of tau protein hyperphosphorylation and senile plaques formed by β-amyloid deposition outside the cells ( senile plaques, SPs), accompanied by cerebral vascular changes and granular vacuolar degeneration. Clinically, the patients gradually develop memory impairment, executive dysfunction, aphas...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12A61K31/4709A61P25/28A61P39/06A61P39/04A61P43/00
CPCA61P25/28A61P39/04A61P39/06A61P43/00C07D401/12
Inventor 黄玲潘廷婷周彦黎兴术
Owner SUN YAT SEN UNIV
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