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4-tertiary butyl benzyl-3,4-dyhydroxyl cinanmate as well as application and preparation method thereof

A use and technology of sodium carbonate, applied in the preparation of carboxylate, chemical instruments and methods, preparation of organic compounds, etc., can solve problems such as bad side effects, and achieve high yield, high clinical application value, and good development prospects. Effect

Active Publication Date: 2015-04-01
北京脉迪法莫医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Neuron damage can lead to a variety of diseases. Currently, there are no effective neuroprotective drugs that can treat these diseases. Only some drugs can alleviate these diseases by improving the function of remaining neurons, and some drugs can also produce undesirable side effects

Method used

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  • 4-tertiary butyl benzyl-3,4-dyhydroxyl cinanmate as well as application and preparation method thereof
  • 4-tertiary butyl benzyl-3,4-dyhydroxyl cinanmate as well as application and preparation method thereof
  • 4-tertiary butyl benzyl-3,4-dyhydroxyl cinanmate as well as application and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of 4-tert-butylbenzyl-3,4-dihydroxycinnamate:

[0037] Caffeic acid (5.0g, 27.8mmol) was added to the HMPA (60ml) solvent, fully stirred at room temperature, the solution was yellow and transparent, anhydrous sodium carbonate solid (3.5g, 33.4mmol) was added, stirring was continued at room temperature for 1 hour, and then A mixture of 4-tert-butylbenzyl bromide (5.6ml, 30.5mmol) dissolved in HMPA (10ml) was slowly dropped into the above reaction solution. Control the temperature at 20°C, stir and react for 20 hours. After TLC confirms that the reaction is complete, pour the reaction solution into 100ml of ice water, add 1N HCl to acidify to pH 6, extract three times with ethyl acetate, combine the organic phases, and successively use 1N HCl40ml and saturated aqueous sodium chloride solution, and the organic phase was dried over anhydrous magnesium sulfate for 3 hours. The solvent was evaporated under reduced pressure, separated and purified on a silica gel ...

Embodiment 2

[0045] Inhibitory effect of 4-tert-butylbenzyl-3,4-dihydroxycinnamate on glutamate-induced death of primary cultured cerebellar granule neurons in rats

[0046] Method and steps:

[0047] Firstly, the primary culture of cerebellar granule neurons (CGN) was carried out. After culturing for 7 days, 4-tert-butylbenzyl-3,4-dihydroxycinnamate (PAR-007, with a final concentration of 10 μM) and caffeic acid phenylethyl ester (CAPE, with a final concentration of 10 μM). Then, neurotoxin glutamate (Glutamate, final concentration 30 μM) was added to the cell culture medium, and the cells were placed in CO 2 Incubator (37°C, 5% CO 2 ) for 24 hours, and finally the cell viability was detected by the FDA / PI double staine method. The results show (see figure 1 ), 30μM glutamic acid (Glutamate) can induce significant death of CGN neurons, while 4-tert-butylbenzyl-3,4-dihydroxycinnamate (PAR-007, final concentration of 10μM) can significantly inhibit The death of neurons significantly p...

Embodiment 3

[0049] Inhibitory effect of 4-tert-butylbenzyl-3,4-dihydroxycinnamate on 6-hydroxydopamine (6-OH-DA)-induced death of primary cultured midbrain dopamine neurons in rats

[0050] Primary cultures of midbrain dopamine neurons were first performed. After culturing for 7 days, 4-tert-butylbenzyl-3,4-dihydroxycinnamate (PAR-007, with a final concentration of 10 μM) and caffeic acid phenylethyl ester (CAPE, with a final concentration of 10 μM). Then, neurotoxin 6-hydroxydopamine (6-hydroxydopamine, final concentration 50 μM) was added to the cell culture medium, and the cells were placed in CO 2 Incubator (37°C, 5% CO 2 ) for 24 hours, and finally the cell viability was detected by MTT assay. The results show (see figure 2 ), 50μM 6-hydroxydopamine can induce significant death of midbrain dopaminergic neurons, while 4-tert-butylbenzyl-3,4-dihydroxycinnamate (PAR-007, final concentration of 10μM) can significantly inhibit The death of neurons significantly protects nerve cells....

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Abstract

The invention provides 4-tertiary butyl benzyl-3,4-dyhydroxyl cinanmate as well as application and a preparation method thereof. The compound has the structure shown in the formula I, and the structure has the important function of neuron protection so that the compound has higher clinical application value and favorable development prospect and can be used for preventing and treating neuron damages and relevant diseases thereof. The preparation method of the compound realizes industrial production with higher yield by using caffeic acid as a raw material and adopting a relatively simple synthesis route and provides powerful guarantee for the production and the clinical application of medicinal preparations.

Description

technical field [0001] The present invention relates to a compound with neuron protective effect and its use and preparation method, in particular to 4-tert-butylbenzyl-3,4-dihydroxycinnamate and its use and preparation method. Background technique [0002] Neuron damage can lead to a variety of diseases. Currently, there are no effective neuroprotective drugs that can treat these diseases. Only some drugs can alleviate these diseases by improving the function of remaining neurons, and some drugs can also produce undesirable side effects . Therefore, it is of great significance to develop new drugs with neuron-protective effects. Contents of the invention [0003] Therefore, the object of the present invention is to provide a compound with neuroprotective effect, which can be used to effectively prevent and / or treat neuron damage and related diseases. [0004] The technical scheme for realizing the above-mentioned purpose is as follows: [0005] Compound shown in formul...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/216C07C69/732C07C67/10A61P25/00
Inventor 刘俊义杜燕生马治中
Owner 北京脉迪法莫医药科技有限公司
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