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A kind of aluminum ion responsive compound and its preparation method and application

A compound and reaction technology, which is applied in the field of aluminum ion-responsive compounds and their preparation, can solve problems such as poor treatment effects of neurodegenerative diseases and side effects of drugs, and achieve enhanced cognitive function, neuron protection, and inhibition of bile Effect of Alkaline Esterase Activity

Active Publication Date: 2021-06-11
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Purpose of the invention: In order to solve the side effects or poor therapeutic effects of existing neurodegenerative disease drugs, one purpose of the present invention is to provide an aluminum ion-responsive compound

Method used

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  • A kind of aluminum ion responsive compound and its preparation method and application
  • A kind of aluminum ion responsive compound and its preparation method and application
  • A kind of aluminum ion responsive compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] The preparation of embodiment 1 compound 1

[0044]

[0045] 1 mmol of 5-chloro-7-formyl-8-hydroxyquinoline was dissolved in 20 ml of methanol, cooled to 10° C. in an ice bath, and then 10 ml of methanolic tacrine solution (containing 1 mmol of tacrine) was slowly added dropwise. After dropping, reacted at room temperature for 2.5 hours, a large amount of precipitates precipitated out, filtered, and the filter cake was washed with a small amount of methanol to obtain the product with a yield of 93%. MS: [M+1]+ =388.

Embodiment 2

[0046] The preparation of embodiment 2 compound 2

[0047]

[0048] The method is the same as in Example 1, except that tacrine is replaced by 9-aminohexylaminotetrahydroacridine to prepare compound 2, yield, 86%, MS: [M+1] + =487.

Embodiment 3

[0049] The preparation of embodiment 3 compound 3

[0050]

[0051] 1 mmol of compound 7 and 1 mmol of compound 8 were dissolved in 20 ml of methanol, stirred and reacted at room temperature for 2.5 h, a large amount of precipitate was precipitated, filtered, and the filter cake was washed with a small amount of methanol to obtain compound 9.

[0052] Compound 9 was directly dissolved in 20 mL of anhydrous DMF without purification, and then 25 mmol of triethylamine and 20 mmol of 4-nitrophenyl chloroformate (1) were added under cooling in an ice bath, and the internal temperature was controlled not to exceed 10°C. Then continue to stir the reaction for 2h, after the TLC tracking reaction is complete, add 9-aminoethylaminotetrahydroacridine (2) (20mmol) to the reaction solution, react at room temperature for 3.5h, filter, concentrate the filtrate, and perform column chromatography (The filler is silica gel; methanol:dichloromethane=1:10v:v) to obtain compound 3 with a yield ...

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Abstract

The invention discloses a compound represented by formula 1, formula 2 or formula 3, and the invention also discloses the preparation method and application of the above compound. Biological activity tests such as aluminum ion response experiments, cholinesterase inhibitory activity experiments, and neuron protection activity experiments were carried out on the above compounds, and it was found that this type of compound has good response characteristics to aluminum ions. The imine bond of the compound will break quickly, and specifically release functional molecules such as cholinesterase inhibitors, neuron protection reagents, fluorescent reagents, etc., thereby protecting neuron cells, inhibiting cholinesterase activity, and enhancing cognitive function and other abilities, indicating that this type of compound has the potential use of targeted therapy for neurodegenerative diseases.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to an aluminum ion-responsive compound and its preparation method and application. Background technique [0002] Neurodegenerative diseases such as Alzheimer's disease (Alzheimer's disease, AD) are common senile diseases, and its mortality rate ranks fourth after cardiovascular disease, cancer, and cerebrovascular disease. Such diseases not only pose a serious threat to human health, but also impose a heavy economic burden on social and economic development. Currently, AD treatment and care alone costs $604 billion worldwide, an amount that exceeds 1% of global GDP. [0003] The etiology of AD is complex. Although it has been discovered for more than a hundred years, its etiology and pathogenesis are still unclear. At present, it is known that the pathological evolution of AD involves multiple systems such as the nervous system, blood circulation system, an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12C07D401/14C07D405/14A61P25/00A61P25/28
CPCC07D401/12C07D401/14C07D405/14
Inventor 房雷李万春
Owner SOUTHEAST UNIV