Benzoate derivatives, preparation method and application

A technology of derivatives, benzoic acid, applied in the fields of benzoic acid ester derivatives and preparation and application, can solve the problems such as no problems, and achieve the effects of simple operation, enhanced memory, and reasonable design

Active Publication Date: 2014-06-25
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 of 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, the ethanol was distilled to obtain a crude product of 390 mg. Silica gel column chromatography (developing solvent: n-hexane / 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 = 8.0 Hz, benzene H-5), 5.66 (s, 1H, benzene 3-OH), 4.41 (q, 2H, J = 7.0 Hz), 1.42 (t, 3H, J=7.0Hz); MS(m / z): 182[M] + .

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

[0045] The synthesis method is the same as that of compound I-1. The reaction ma...

Embodiment 2

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

[0084] The synthesis method is the same as that of compound I-4, and the reaction materials are: (110mg, 1mmol) catechol, (310mg, 1mmol) eicosanic acid, (250mg, 1.2mmol) dicyclohexylcarbodiimide, 15ml tetrahydrofuran to obtain white Solid 391mg, 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 the protection of nitrogen, put (110mg, 1mmol) hydroquinone, (280mg, 5mmol) potassium hydroxide, 10ml N, N-dimethylformamide in a 25ml round bottom flask, and add (830mg, 3mmol) dropwise Bromotetradecane. Stir at room temperature overnight. After the reaction stops, the system is poured into a large amount of distilled water, and a yellow solid is obtained by chromatography, filtered, washed with water and washed with 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 uses of benzoate and its derivatives for anti-aging of brain, and for preventing and treating the neurodegenerative diseases such as the senile dementia and the like are provided in the present invention. A series of benzoate and its derivatives are synthesized through a chemical method in the present invention. Proved through cell activity experiments in vitro, the synthesized benzoate and its derivatives have distinguished activities similar to nerve growth factors. Proved through an animal experiment, benzoate and its derivatives do not induce toxic reaction during long term oral or celiac administration, they are able to cross the blood-brain barrier and promote the regeneration of cerebral neuron.

Description

Technical field [0001] The present invention belongs to a compound preparation method and application, and relates to a preparation method of benzoate derivatives, and the application of the compound in the prevention and treatment of neurodegenerative diseases such as Alzheimer's disease. Background technique [0002] Alzheimer’s disease can be roughly divided into three types: Alzheimer’s disease (AD), vascular dementia and other types of dementia. With the increase in the elderly 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. The number of patients with Alzheimer’s disease in my country is estimated to exceed 5 million, accounting for about 1 / 4 of the total number of cases in the world. Moreover, with the acceleration of the aging process of our country’s population, this number will be even greater, which will have a significant impact o...

Claims

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Application Information

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Patent Type & Authority Patents(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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