4-cyclamine alkoxy-3-methoxyl cinnamic acid benzamide compound, preparation method and application of compound

The technology of benzamide cinnamate and cycloamine alkoxy is applied in the field of drugs for treating and/or preventing neurodegenerative diseases, and can solve the problems of many toxic and side effects, single target of action, poor long-term efficacy in AD patients, and the like, To achieve cell damage protection, cell damage significant effect

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-cyclamine alkoxy-3-methoxyl cinnamic acid benzamide compound, preparation method and application of compound
  • 4-cyclamine alkoxy-3-methoxyl cinnamic acid benzamide compound, preparation method and application of compound
  • 4-cyclamine alkoxy-3-methoxyl cinnamic acid benzamide compound, preparation method and application of compound

Examples

Experimental program
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Effect test

Embodiment 1-15

[0044] A preparation method of 4-cycloamine alkoxy-3-methoxycinnamic acid benzamide compound, comprising the following steps:

[0045] The first step, add ferulic acid, the first solvent, condensing agent and 2-methylaniline in the reaction bottle, stir the reaction, the reaction process is tracked by TLC; after the reaction is completed, the solvent is evaporated under reduced pressure, and the residue is added Dichloromethane was washed successively with saturated aqueous sodium carbonate and saturated aqueous sodium chloride, the organic layer was dried over anhydrous sodium sulfate and filtered, the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (eluent: dichloromethane : methyl alcohol=30:1v / v), get corresponding ferulic acid benzamide compounds;

[0046] In the second step, the above-mentioned ferulic acid benzamide compound is dissolved in the second solvent, and the base used in the first basic condition and 1-(2'-m...

Embodiment 16

[0055] 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.

[0056] Table 5 Different Substituent Experiments

[0057]

[0058]

[0059]

Embodiment 17

[0061] A preparation method of a pharmaceutically acceptable salt of a 4-cycloamine alkoxy-3-methoxycinnamic acid benzamide compound, comprising the following steps:

[0062] Take the 4-cycloaminealkoxy-3-methoxycinnamic acid benzamide compound and acetone respectively in Table 5 and stir evenly, then add the acid, heat up and reflux, stir and react for 15-30 minutes, cool to room temperature after the reaction, and reduce The solvent is removed by steaming under pressure, the residue is recrystallized with acetone, and the precipitated solid is filtered to obtain a pharmaceutically acceptable salt of 4-cycloaminoalkoxy-3-methoxycinnamic acid benzamide compound. 1 Confirmed by HNR and ESI-MS.

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PUM

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Abstract

The invention relates to a 4-cyclamine alkoxy-3-methoxyl cinnamic acid benzamide compound, a preparation method and application of the compound.The chemical structure general formula of the compound is shown as a formula (I) (please see the formula in the description), wherein m represents 1-12, R1 represents C1-C12 alkyl or benzyl or substituted benzyl, X represents C1-C12 alkyl or benzyl or substituted benzyl, phenyl of which a benzene ring is substituted with 1-4 groups selected from F, Cl, Br, I, C(1-4) alkyl, C(1-4) alkoxy, trifluoromethyl, trifluoromethoxy, nitryl, a cyano group, and the substituent groups can be located at any position of the benzene ring.Accordingly, the compound has the significant inhibiting effect on acetylcholinesterase, the IC50 of the compound is 0.01-5 micromoles per liter, the inhibiting activity on acetylcholinesterase is greatly higher than the inhibiting activity on butyrylcholine esterase, and therefore the compound has the certain selective inhibiting effect on acetylcholinesterase.

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-methoxycinnamic acid benzamide 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 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/22A61K31/445A61P25/28A61P25/16A61P27/06A61P25/02A61P25/04A61P25/14A61P37/06A61P17/00
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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