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Benzamide derivant and preparation method and application thereof

A technology of benzamide and derivatives, which is applied in the field of benzamide derivatives and their preparation and application, can solve problems such as not yet known, and achieve the effect of simple operation, reasonable design, and enhanced memory

Inactive Publication Date: 2015-03-11
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, no researchers have discovered such substances from natural products, let alone reports that such compounds have anti-senile dementia-like NGF activity

Method used

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  • Benzamide derivant and preparation method and application thereof
  • Benzamide derivant and preparation method and application thereof
  • Benzamide derivant and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Compound Ⅰ-1: Ethyl 2,3-dihydroxybenzoate

[0044] Put (154mg, 1mmol) 2,3-dihydroxybenzoic acid and 10ml ethanol in a 25ml round bottom flask, cool to 0°C, add 2~3 drops of concentrated sulfuric acid dropwise, and stir at reflux for 24h. The reaction was followed by thin-layer chromatography (developing solvent: n-hexane / ethyl acetate, 5 / 1, V / V). After the reaction stopped, ethanol was distilled off to obtain 390 mg of crude product. Silica gel column chromatography (developing solvent: n-hexane / ethyl acetate Ethyl acetate, 5 / 1, V / V), to obtain 180 mg of white solid, yield: 99%. 1 H NMR (500MHz, CDCl 3 )δ:11.00(s,1H,benzene 2-OH),7.38(dd,1H,J=1.5,8.0Hz,benzene H-6),7.12(dd,1H,J=1.0,7.5Hz,benzene H- 4),6.80(t,1H,J=8.0Hz,benzene H-5),5.66(s,1H,benzene 3-OH),4.41(q,2H,J=7.0Hz),1.42(t,3H, J=7.0Hz); MS(m / z):182[M] + .

[0045] Compound Ⅰ-2: Amyl 2,3-dihydroxybenzoate

[0046] The synthesis method is the same as compound Ⅰ-1, and the reaction materials are: (154mg, 1mmo...

Embodiment 2

[0084] Compound Ⅱ-1: 1,2-phenylene eicosate

[0085] The synthesis method is the same as compound Ⅰ-4, and the reaction materials are: (110mg, 1mmol) o-diphenol, (310mg, 1mmol) eicosanoic acid, (250mg, 1.2mmol) dicyclohexylcarbodiimide, 15ml tetrahydrofuran, and white Solid 391 mg, yield: 56%. 1 H NMR (500MHz, CDCl 3 )δ:7.13~7.16(t,1H,J=7.5Hz),7.09~7.11(d,1H,J=7.5Hz),7.02~7.04(d,1H,J=7.5Hz),6.92~6.95(t ,1H,J=7.5Hz),2.63(t,2H,J=6.5Hz),2.42(t,2H,J=6.5Hz),1.96~1.99(m,12H),1.17~1.42(m,60H) ,0.89(bs,6H);MS(m / z):699[M] + .

Embodiment 3

[0087] Compound Ⅲ-1: 1,4-bis(tetradecyloxy)benzene

[0088] Under nitrogen protection, put (110mg, 1mmol) hydroquinone, (280mg, 5mmol) potassium hydroxide, 10ml N,N-dimethylformamide in a 25ml round bottom flask, drop (830mg, 3mmol) Bromotetradecane. Stir overnight at room temperature. After the reaction stops, pour the system into a large amount of distilled water. A yellow solid precipitates in the upper layer, which is filtered, washed with water and 10% sodium hydroxide to obtain 111 mg of the product, yield: 22%. 1 H NMR (500MHz, CDCl 3 )δ:6.76(bs,4H),3.75~3.80(t,4H,J=6.5Hz),1.82(m,4H),1.25~1.33(m,44H),0.85(t,6H,J=7.0Hz );MS(m / z):502[M] + .

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Abstract

The invention provides a benzamide derivant. A chemical method is utilized to combine a series of benzoate derivants including ester compounds, (sulfur) ether compounds and amide compounds. Most combined compounds have new chemical structure. An external cell viability experiment verifies that the combined benzoate derivant has remarkable viability similar to nerve growth factor (NGF). An internal animal experiment verfies that the combined new compound 2,3- dihydroxy-benzoic acid-14 ester has the effect of strengthening memory of aged mouse. Therefore, the benzoate derivant can be applied in preparation of medicine for preventing and treating neurodegenerative diseases like senile dementia, particularly being applied to preparation of medicine for treating Alzheimer's disease (AD) and other neurodegenerative diseases. By means of the method, new medicine use of the benzoate derivant is developed. The preparation method is reasonable and convenient to operate. The benzamide derivant provides new medicines for treatment of neurodegenerative diseases like senile dementia.

Description

[0001] (This case is a divisional application with application number: 2001010103089.6, titled Benzoate Derivatives, Preparation Methods and Applications) technical field [0002] The invention belongs to the preparation method and application of compounds, and relates to the preparation method of benzoate derivatives and the application of such compounds in the prevention and treatment of neurodegenerative diseases such as senile dementia. Background technique [0003] Alzheimer's disease can be roughly divided into three types: Alzheimer's disease (AD for short), vascular dementia and other types of dementia. With the increase of the aging population, the prevalence of senile dementia has increased significantly, and it has become the fourth leading cause of death in adults, second only to heart disease, cancer, and stroke. It is estimated that there are more than 5 million senile dementia patients in my country, accounting for about 1 / 4 of the total number of cases in the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C235/60C07C231/02A61P25/28
Inventor 戚建华罗燕向兰高丽娟孙恺悦李金优韩峰
Owner ZHEJIANG UNIV
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