Cyclamine alkylamide ferulate compound as well as preparation method and application thereof

The technology of acid cyclic amine alkyl amide and phthalimide alkyl amine is applied in the field of ferulic acid cyclic amine alkyl amide compound and its preparation, and can solve the problem of single action target, many toxic and side effects, AD patients have problems such as poor long-term efficacy, and achieve the effect of good therapeutic effect, convenient operation and high product yield

Inactive Publication Date: 2016-07-20
NANYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Cyclamine alkylamide ferulate compound as well as preparation method and application thereof
  • Cyclamine alkylamide ferulate compound as well as preparation method and application thereof
  • Cyclamine alkylamide ferulate compound as well as preparation method and application thereof

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preparation example Construction

[0041] The preparation method of the ferulic acid cyclic aminoalkyl amides compound of above-mentioned embodiment 1, comprises the following steps:

[0042] a. Add 10mmol phthalimide potassium salt (1), 30mL acetone, 12mmol anhydrous potassium carbonate and 12mmol 1-substituted-4-chloroalkylpiperidine (2) into the reaction flask, heat up to 60°C and reflux Stir the reaction for 20 hours. After the reaction is over, filter while hot, wash the filter cake with a small amount of acetone, evaporate the filtrate to remove the solvent under reduced pressure, and purify the residue by column chromatography (eluent: chloroform) to obtain phthalimide alkane Base amine compound (3), yield is 97.5%;

[0043] b. Dissolve all the above intermediate (3) in 50mL ethanol, add 30mmol N 2 h 4 .H 2 O, heat up to 80° C., reflux and stir for 8 hours. After the reaction, suction filter while hot, wash the filter cake with a small amount of ethanol, evaporate the filtrate to remove the solvent un...

Embodiment 1-60

[0049] Table 1 Embodiments of the present invention 1-60 ferulic acid cyclic amine alkyl amides compounds

[0050]

[0051]

[0052]

[0053] Table 2 One of the parameters of the preparation method of 1-10 ferulic acid cyclic amine alkyl amides of the present invention

[0054]

[0055]

Embodiment 1-10

[0056] Table 3 Embodiment 1-10 of the present invention The second parameter of the preparation method of ferulic acid cyclic amine alkyl amides compound

[0057]

[0058] Table 4 The third parameter of the preparation method of the embodiment of the present invention 1-11 ferulic acid cyclic amine alkyl amides compound

[0059]

[0060]

[0061] Preparation of Ferulic Acid Cyclic Amino Alkyl Amide Compound (I) and Acid Synthetic Salt

[0062] Add 2.0mmol of ferulic acid cyclic amine alkyl amides compound (I) and 50ml of acetone prepared according to the above-mentioned embodiment 1 in the reaction flask, add 6.0mmol tartaric acid after stirring evenly, heat up and reflux stirring reaction for 20min, cool to At room temperature, the solvent is evaporated under reduced pressure, the residue is recrystallized with acetone, and the precipitated solid is filtered to obtain the salt of ferulic acid cyclic aminoalkylamide compound (I). 1 Confirmed by HNR and ESI-MS.

[00...

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Abstract

The invention belongs to the technical field of organic synthesis and particularly relates to a cyclamine alkylamide ferulate compound as well as a preparation method and application thereof. The preparation method comprises the following steps: enabling potassium phthalimide serving as a start raw material to react with 1-substituted-4-haloalkyl piperidine under the effects of a solvent and alkali to obtain a phthalimide alkylamine compound; performing hydrazinolysis of the phthalimide alkylamine compound and hydrazine hydrate to obtain a primary amine compound; and adding ferulic acid, a condensing agent and a solvent into the primary amine compound for a condensation reaction to obtain a product of cyclamine alkylamide ferulate compound. The cyclamine alkylamide ferulate compound provided by the invention is of a simple chemical structure, the chemical reactions in the preparation process are thorough, the product yield is high, the operation is convenient, the cost is low, and the product can be used for perfectly treating the neurodegenerative diseases.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a ferulic acid cyclic amine alkyl amide compound and its preparation method and application. Background technique [0002] Vascular dementia (Vascular Dementia, VD) is a symptom of intelligence and cognitive dysfunction caused by various types of cerebrovascular diseases such as ischemic cerebrovascular disease, hemorrhagic cerebrovascular disease, acute and chronic hypoxic cerebrovascular disease, etc. Clinical syndrome, whose main clinical manifestations include: decline in cognitive ability, memory and social life ability, and changes in emotion and personality, 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 gradually inc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/26A61K31/44A61P25/28
CPCC07D211/26
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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