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4-amine alkoxy-3-methoxyl cinnamic acid ester compound, preparation method and application of compound

A methoxycarnitine and amine alkoxy technology, which is applied in the field of drugs for the treatment and/or prevention of neurodegenerative-related diseases, can solve the problems of many toxic and side effects, a single target of action, and poor long-term efficacy in AD patients. Cell damage protection, significant effect of cell damage

Inactive Publication Date: 2016-07-06
NANYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these drugs have problems such as single target, many toxic and side effects, and poor long-term curative effect on AD patients.

Method used

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  • 4-amine alkoxy-3-methoxyl cinnamic acid ester compound, preparation method and application of compound
  • 4-amine alkoxy-3-methoxyl cinnamic acid ester compound, preparation method and application of compound
  • 4-amine alkoxy-3-methoxyl cinnamic acid ester compound, preparation method and application of compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-15

[0058] A preparation method of 4-aminoalkoxy-3-methoxycinnamate compound, comprising the following steps:

[0059] The first step, add ferulic acid, the first solvent, catalytic amount DMF and acylating agent in reaction bottle, the addition amount of catalyzer is 0.05% of ferulic acid weight, heats up and refluxes and stirs reaction, evaporates under reduced pressure and removes solvent, obtains Ferulic acid chloride;

[0060] In the second step, the above-mentioned ferulic acid chloride is dissolved in the second solvent, and the alkali and ethanol used in the first basic condition are added, and the reaction is stirred, and the reaction process is followed by TLC; after the reaction is completed, the solvent is evaporated under reduced pressure, and the residue is Add the second solvent, wash with saturated aqueous sodium carbonate and saturated aqueous sodium chloride successively, filter the organic layer after drying over anhydrous sodium sulfate, distill off the solvent...

Embodiment 15

[0065] Substantially the same as Example 7, the difference of the first step is: the catalyst used is the mixture of DMF, pyridine and aluminum chloride, the DMF add-on is 0.03% of the ferulic acid weight, the pyridine add-on is the ferulic acid 0.01% by weight, and the addition of aluminum trichloride is 0.005% by weight of ferulic acid. See Table 1-4 for the differences in other steps.

[0066] Table 1 Process conditions and results of the first step

[0067]

[0068] As can be seen from Table 1, the process conditions have a serious impact on the yield of the product, and selecting suitable process conditions has an important meaning to the product yield. It can be seen from Table 1 that the first solvent is dichloromethane:toluene with a volume ratio of 2:1, the acylating agent is thionyl chloride, the molar feeding ratio is 1:3, the reaction temperature is 70°C, and the reaction time is 6h. , the yield is 86.8%, and the yield is very high.

[0069] As can be seen fr...

Embodiment 16

[0080] The specific process conditions are the same as in Example 7, and the difference is the same as the investigation of different substituents. The specific substituents are shown in Table 5, and the obtained 4-aminoalkoxy-3-methoxycinnamate compounds have their chemical structures verified. 1 H-NMR, 13 Confirmed by C-NMR and ESI-MS.

[0081] Table 5 Different Substituent Experiments

[0082]

[0083]

[0084]

[0085]

[0086]

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PUM

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Abstract

The invention relates to a 4-amine alkoxy-3-methoxyl cinnamic acid ester compound, a preparation method and application of the compound.The preparation method of the compound comprises the following steps that 1, a ferulic acid acyl chloride compound is obtained by taking ferulic acid as a staring material under the condition of in first solvent under the condition of an acylating agent; 2, the ferulic acid acyl chloride compound reacts with alcohol or phenol in second solvent under a first alkaline condition to obtain a corresponding cinnamic acid ester compound; 3, the cinnamic acid ester compound reacts with a dihalogen alkyl compound in third solvent under a second alkaline condition to generate a corresponding halogen compound; 4, the halogen compound reacts with an organic amine compound in fourth solvent to obtain the 4-amine alkoxy-3-methoxyl cinnamic acid ester compound.Accordingly, the compound has the significant inhibiting effect on acetylcholinesterase, the inhibiting activity on acetylcholinesterase is greatly higher than the inhibiting activity on butyrylcholine esterase, and the certain selective inhibiting effect on acetylcholinesterase is achieved.

Description

technical field [0001] The invention relates to a medicine for treating and / or preventing neurodegenerative related diseases, in particular to a 4-aminoalkoxy-3-methoxycinnamate compound, a preparation method and its use. Background technique [0002] Vascular Dementia (VD) is a mental and cognitive disorder caused by various types of cerebrovascular diseases (including ischemic cerebrovascular disease, hemorrhagic cerebrovascular disease, acute and chronic hypoxic cerebrovascular disease, etc.). The clinical syndrome of functional impairment, its main clinical manifestations include: decline in cognitive ability, memory, and social life ability, as well as changes in emotion and personality. It is a chronic progressive disease. In China, Japan and other Asian countries, vascular dementia is the first cause of senile dementia; with the continuous advancement of the world's population to aging, cerebrovascular diseases are increasing, and the incidence of vascular dementia is...

Claims

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Application Information

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IPC IPC(8): C07C217/20C07C213/02C07D211/14C07D295/088A61P25/28A61P25/16A61P27/06A61P25/02A61P25/04A61P25/14A61P37/06A61P17/00
CPCC07C51/60C07C67/14C07C67/31C07C213/02C07C217/20C07D211/14C07D295/088C07C69/734C07C69/736C07C59/64
Inventor 桑志培柳文敏于林涛马勤阁陈长中潘万里李涛高利敏
Owner NANYANG NORMAL UNIV
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