4-cycloaminoalkoxy-3-methoxycinnamates, and preparation method and application thereof

A cycloamine alkoxy, methoxy meat technology, applied in organic chemistry, drug combination, pharmaceutical formulations, etc., can solve the problems of many toxic and side effects, single action target, poor long-term efficacy in AD patients, etc. Damage protection, significant effect of cell damage

Inactive Publication Date: 2016-06-01
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-cycloaminoalkoxy-3-methoxycinnamates, and preparation method and application thereof
  • 4-cycloaminoalkoxy-3-methoxycinnamates, and preparation method and application thereof
  • 4-cycloaminoalkoxy-3-methoxycinnamates, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-15

[0048] A preparation method of 4-cycloamine alkoxy-3-methoxycinnamate compound, comprising the following steps:

[0049] 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 compound;

[0050] In the second step, the above-mentioned ferulic acid chloride compound is all 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 residual The second solvent was added to the mixture, washed successively with saturated aqueous sodium carbonate and saturated aqueous sodium chloride, the organic layer was dried over anhydrous ...

Embodiment 15

[0054] 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.

[0055] Table 1 Process conditions and results of the first step

[0056]

[0057] 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.

[0058] As can be seen fr...

Embodiment 16

[0066] 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.

[0067] Table 5 Different Substituent Experiments

[0068]

[0069]

[0070]

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Abstract

The invention relates to 4-cycloaminoalkoxy-3-methoxycinnamates, and a preparation method and application thereof. The preparation method is characterized by comprising the following steps: 1. preparing ferulic acid acyl chlorides from the initial raw material ferulic acid under the conditions of a first solvent and an acylating agent; 2. carrying out reaction on the ferulic acid acyl chlorides and alcohol or phenol in a second solvent under the first alkaline condition to obtain corresponding ferulates; and 3. carrying out reaction on the ferulates and 1-substituted-4-chloroalkylpiperidine in a third solvent under the second alkaline condition to generate the 4-cycloaminoalkoxy-3-methoxycinnamates. The compounds have favorable effects on treating and/or preventing neurodegeneration related diseases, including but not limited to vascular dementia, Alzheimer's disease, Parkinson's disease, Huntington's disease, HIV (human immunodeficiency virus) related dementia, multilocular sclerosis, progressive lateral spinal sclerosis, neuropathic pains, glaucoma and the like.

Description

technical field [0001] The invention relates to a medicine for treating and / or preventing neurodegenerative related diseases, in particular to a 4-cycloaminoalkoxy-3-methoxycinnamate compound, a preparation method and use thereof. 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 de...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/22A61K31/4409A61P25/28A61P25/16A61P25/14A61P25/04A61P27/06A61P21/00A61P25/00
CPCC07D211/22
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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