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Benzoate derivatives, preparation method and application

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

Active Publication Date: 2010-09-01
杭州常青藤医药科技有限公司
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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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  • Benzoate derivatives, preparation method and application
  • Benzoate derivatives, preparation method and application
  • Benzoate derivatives, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Compound I-1: Ethyl 2,3-dihydroxybenzoate

[0043] 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. Track the reaction with thin layer chromatography (developing agent: n-hexane / ethyl acetate, 5 / 1, V / V). After the reaction stops, ethanol is evaporated to obtain 390 mg of crude product. Silica gel column chromatography (developing agent: 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, 8.0 Hz, Benzene H-6), 7.12 (dd, 1H, J = 1.0, 7.5 Hz, 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] + .

[0044] Compound I-2: Amyl 2,3-dihydroxybenzoate

[0045] The synthesis method was the same as that of compound I-1, and the reactio...

Embodiment 2

[0083] Compound II-1: 1,2-phenylene eicosate

[0084] The synthesis method is the same as that of compound I-4, and the reaction materials are: (110mg, 1mmol) o-diphenol, (310mg, 1mmol) eicosanoic acid, (250mg, 1.2mmol) dicyclohexylcarbodiimide, 15ml tetrahydrofuran, and a 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

[0086] Compound III-1: 1,4-bis(tetradecyloxy)benzene

[0087] Under nitrogen protection, (110mg, 1mmol) hydroquinone, (280mg, 5mmol) potassium hydroxide, 10ml N,N-dimethylformamide were placed in a 25ml round bottom flask, and (830mg, 3mmol) was added dropwise 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 benzoate derivatives. A series of benzoate derivatives are synthesized through a chemical method, comprising ester compounds, (sulfur) ether compounds and amide compounds, wherein most synthesized compounds have new chemical structures, and proved through in vitro cell activity experiments, the synthesized benzoate derivatives have obvious activities similar to nerve growth factors (NGF). Proved through an in vitro animal experiment, 2,3-dyhydroxy benzoic acid tetradecyl ester which is a new synthesized compound has the effect of enhancing the memory of senile mice, thus the benzoate derivative can be applied to preparing medicaments for preventing and treating senile dementia neurodegenerative diseases, particularly to preparing medicaments for treating the neurodegenerative diseases such as the Alzheimer's diseases (AD), and the like. The invention opens up a new medical application of the benzoate derivatives, has reasonable preparation method and simple and convenient operation and provides new treatment medicaments for preventing and treating the neurodegenerative diseases such as the senile dementia, and the like.

Description

technical field [0001] 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 [0002] 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 Alzheimer's disease 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 world; moreover, with the acceleration of the aging process of my country's population, this number will become even larger, which will have a significa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/46C07C69/94C07C69/92C07C69/84C07C69/28C07C69/24C07C67/08C07C43/205C07C41/16C07C231/12C07C231/02A61K31/235A61K31/222A61K31/166A61K31/09A61P25/28A61P25/00
CPCA61K31/609A61K31/618A61K31/222A61K31/235A61K31/09A61P25/00A61P25/28
Inventor 戚建华罗燕向兰高丽娟孙恺悦李金优韩峰
Owner 杭州常青藤医药科技有限公司
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