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2-Hydroxybenzamide-1,2,3,4-tetrahydroisoquinoline-o-carbamate compound and preparation method thereof

A technology of hydroxybenzamide and tetrahydroisoquinoline, applied in the direction of organic chemistry, drug combination, nervous system diseases, etc., to achieve the effect of dose-dependent improvement

Active Publication Date: 2020-07-03
NANYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the primary stage of AD, the acetylcholinesterase in the brain of the patient is significantly enhanced. However, this patent is a highly efficient and highly selective butyrylcholinesterase inhibitor, which has no inhibitory activity on acetylcholinesterase. degree AD is less meaningful

Method used

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  • 2-Hydroxybenzamide-1,2,3,4-tetrahydroisoquinoline-o-carbamate compound and preparation method thereof
  • 2-Hydroxybenzamide-1,2,3,4-tetrahydroisoquinoline-o-carbamate compound and preparation method thereof
  • 2-Hydroxybenzamide-1,2,3,4-tetrahydroisoquinoline-o-carbamate compound and preparation method thereof

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Embodiment 1-54

[0047] Table 1 Embodiment 1-54 compound structural formula of the present invention

[0048]

[0049]

[0050]

[0051]

[0052] The preparation method of the 2-hydroxybenzamide-1,2,3,4-tetrahydroisoquinoline-O-carbamate compound (I) of the above-mentioned embodiment 1 comprises the following steps:

[0053] a. Add 10mmol hydroxybenzoic acid (1), 10mmol substituted 1,2,3,4-tetrahydroisoquinoline (2), 15mmol EDCI, 15mmol HOBT and 50mLTHF into the reaction flask, stir at 25°C for 12h, and evaporate to dryness under reduced pressure solvent, adding deionized water, extracting with dichloromethane, washing the organic layer with saturated sodium chloride, evaporating the solvent under reduced pressure, and purifying the residue by column chromatography (petroleum ether: acetone=100:1v / v) to obtain Corresponding hydroxybenzamide intermediate (3);

[0054] b. 10mmol of hydroxybenzamide intermediate (3), 10mmol of the corresponding carbamoyl chloride (4), 11mmol of anhyd...

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Abstract

The invention belongs to the technical field of organic synthesis, and particularly relates to a 2-hydroxybenzamido-1,2,3,4-tetrahydroisoquinolyl-O-carbamate compound and a preparation method thereof.The 2-hydroxybenzamido-1,2,3,4-tetrahydroisoquinolyl-O-carbamate compound adopts a chemical structural formula as shown in a formula (I). The 2-hydroxybenzamido-1,2,3,4-tetrahydroisoquinolyl-O-carbamate compound has a significant inhibiting effect on both acetylcholinesterase and butyrylcholinesterase, has a strong complexing effect on metal ions, has strong antioxidant activity, has a significant protective effect on Abeta1-42-induced SH-SY5Y cell damage and has a significant protective effect on hydrogen peroxide-induced PC12 cell damage.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a 2-hydroxybenzamide-1,2,3,4-tetrahydroisoquinoline-O-carbamate compound and a preparation method thereof. Background technique [0002] 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 in the world suffered from dementia in 2015. It is predicted that by 2050, the world's There will be 131.5 million people suffering from dementia, and the incidence rate of dementia patients in China has reached 6.61%. With the prolongation of the average life expectancy, the disease has developed into a major burden on the society and the medical care system, and has brought heavy mental and economic pressure to the society, patients and their families. Therefore, it is of great signific...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D217/04C07D217/20C07D217/26C07D217/16A61P25/00
CPCA61P25/00C07D217/04C07D217/16C07D217/20C07D217/26
Inventor 桑志培柳文敏王柯人马勤阁王慧娟韩雪刘青妹冉亚文
Owner NANYANG NORMAL UNIV