4-amino alkoxy-3-methoxy cinnamic acid benzamide compounds as well as preparation methods and applications thereof

A technology of cinnamic acid benzamide and methoxycinnamic acid, which is applied in the field of preparation of 4-aminoalkoxy-3-methoxycinnamic acid benzamide compounds, can solve the problem of multiple toxic and side effects, single action target, AD Patients with poor long-term curative effect and other problems, to achieve the effect of cell damage protection and cell damage

Inactive Publication Date: 2016-07-27
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-amino alkoxy-3-methoxy cinnamic acid benzamide compounds as well as preparation methods and applications thereof
  • 4-amino alkoxy-3-methoxy cinnamic acid benzamide compounds as well as preparation methods and applications thereof
  • 4-amino alkoxy-3-methoxy cinnamic acid benzamide compounds as well as preparation methods and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-15

[0051] A preparation method of 4-aminoalkoxy-3-methoxycinnamic acid benzamide compound, comprising the following steps:

[0052] The first step, add ferulic acid, the first solvent, condensing agent and aniline in reaction bottle, stir reaction, reaction progress is tracked with TLC; Wash with saturated aqueous sodium carbonate and saturated aqueous sodium chloride, dry the organic layer over anhydrous sodium sulfate and filter, distill off the solvent under reduced pressure, and purify the residue by column chromatography (eluent: dichloromethane: methanol = 30: 1v / v), get corresponding ferulic acid benzamide compounds;

[0053] Second step, the above-mentioned ferulic acid benzamide compounds are dissolved in the second solvent, add the used alkali and dibromoethane under the first basic condition, heat up and reflux and stir the reaction, the reaction process is followed by TLC, after the reaction finishes, press The solvent and excess dibromoethane were evaporated, and th...

Embodiment 16

[0066] The specific process conditions are the same as in Example 7, and the difference is the same as that of investigating different substituents. The specific substituents are shown in Table 4. The obtained 4-aminoalkoxy-3-methoxycinnamic acid benzamides have the same chemical structure. through 1 H-NMR, 13 Confirmed by C-NMR and ESI-MS.

[0067] Table 4 Different Substituent Experiments

[0068]

[0069]

[0070]

[0071]

[0072]

Embodiment 17

[0074] A preparation method of a pharmaceutically acceptable salt of a 4-aminoalkoxy-3-methoxycinnamic acid benzamide compound, comprising the following steps:

[0075] Take the 4-aminoalkoxy-3-methoxycinnamic acid benzamide compound and acetone respectively in Table 4 and stir evenly, then add the corresponding acid, heat up and reflux and stir for 15-30 minutes, and cool to room temperature after the reaction. The solvent was distilled off under reduced pressure, the residue was recrystallized with acetone, and the precipitated solid was filtered to obtain a pharmaceutically acceptable salt of 4-aminoalkoxy-3-methoxycinnamic acid benzamide compound. 1 HNR, 13 Confirmed by CNMR and ESI-MS.

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Abstract

The invention relates to 4-amino alkoxy-3-methoxy cinnamic acid benzamide compounds as well as preparation methods and applications thereof. The preparation methods of the compounds comprise the following steps: step 1, ferulic acid is taken as a starting material and subjected to a reaction with substituted aniline under the conditions of a first solvent and a condensing agent, and corresponding ferulic acid benzamide compounds are obtained; step 2, the ferulic acid benzamide compounds are subjected to a reaction with a dihalogenated alkyl compound under the condition of a second solvent and a first alkaline condition, and a corresponding halogen compounds are obtained; step 3, the halogen compounds are subjected to a reaction with an organic amine compound under the condition of a third solvent, and the 4-amino alkoxy-3-methoxy cinnamic acid benzamide compounds are obtained. The compounds have a remarkable inhibiting effect on acetylcholinesterase, the IC50 is 0.01 mu M-5 mu M, and the inhibitory activity on acetylcholinesterase is greatly higher than that on butyrylcholinesterase, so that the compounds have 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-aminoalkoxy-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 of va...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/12C07C235/38C07D295/088C07D211/14A61K31/167A61K31/495A61K31/4453A61K31/445A61P25/28
CPCC07C233/58C07D211/14C07D295/088
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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