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Compound and application thereof as L-calcium channel retarder or/and acetylcholinesterase inhibitor

A compound, Y-L-X technology, applied in the application of L-type calcium channel blockers or/and acetylcholinesterase inhibitors. In the field of compounds, it can solve the problems of lack of acetylcholine, failure of nerve signal transmission, affecting the body's cognition and memory, etc. , to achieve a significant inhibitory effect on

Active Publication Date: 2012-05-23
JIANGSU SIMCERE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because acetylcholinesterase can catalyze the cleavage reaction of acetylcholine, it will lead to the loss of acetylcholine and the failure of nerve signal transmission, thus affecting the body's cognition, memory and other functions

Method used

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  • Compound and application thereof as L-calcium channel retarder or/and acetylcholinesterase inhibitor
  • Compound and application thereof as L-calcium channel retarder or/and acetylcholinesterase inhibitor
  • Compound and application thereof as L-calcium channel retarder or/and acetylcholinesterase inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0143] Embodiment 1 prepares compound 1 provided by the invention

[0144] The preparation process is as follows:

[0145]

[0146] Accurately weigh 3.0g of about 24.6mmol of 3-hydroxybenzaldehyde, dissolve it in 100mL of acetone, stir to dissolve, add 6.8g, equivalent to 50mmol of K 2 CO 3 Solid powder, stirred vigorously, and then slowly added dropwise 2.75g (25.6mmol) of N,N-dimethylformyl chloride, a small amount of bubbles were generated. After the reaction is stable, move the reactor into a 60°C oil bath and heat to reflux, TLC detection, stop the reaction after 21h, cool, filter, discard the filter residue, evaporate the filtrate to dryness and add saturated NaHCO 3 The solution was diluted, left to stand and separated and extracted with ethyl acetate, the organic extract was collected, washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain an oily substance, which was purified by silica gel column chroma...

Embodiment 2

[0151] Embodiment 2 prepares compound 2 provided by the invention

[0152] The preparation process is as follows:

[0153]

[0154] Accurately weigh 2.0 g of isopropyl acetoacetate, dissolve it in 15 mL of absolute ethanol, then add 1.6 g of about 20.83 mmol of ammonium acetate, heat to reflux in an oil bath at 90°C, detect by TLC, stop the reaction after 24 hours, evaporate under reduced pressure at low temperature dry reaction solution, to obtain compound S 1 2.0 g, yield 100%. ESI-MS[M+H] + = 144.1.

[0155] Weigh 1.0g of about 4.0mmol of 3-hydroxybenzaldehyde, dissolve it in 50mL of acetone, stir to dissolve, then add 2.3g of about 16.3mmol of K 2 CO 3 Solid powder, after stirring vigorously, slowly add 0.5g of about 4.5mmol of N,N-dimethylformyl chloride dropwise, a small amount of bubbles are generated, after the reaction is stable, heat and reflux in an oil bath at 60°C, detect by TLC, stop after 12h React, cool, filter, discard the filter residue, collect the ...

Embodiment 3

[0161] Embodiment 3 prepares compound 3 provided by the invention

[0162] The preparation process is as follows:

[0163]

[0164]Accurately weigh 0.5g of 3-nitro-4-hydroxybenzaldehyde equivalent to 2.99mmol, dissolve it in 5mL of anhydrous pyridine solution, stir to dissolve, then slowly add 0.38g of about 3.55mol of N,N-dimethyl Phyloyl chloride, a small amount of bubbles are generated, after the reaction is stable, let it stand at room temperature, TLC detection, stop the reaction after 14h, there is solid precipitation, filter and discard the filter residue, collect the filtrate and dilute with ethyl acetate, then add dropwise 1mol / L of hydrochloric acid to adjust the pH value to >7, extract the organic layer, wash with water, dry over anhydrous sodium sulfate, filter, and concentrate under reduced pressure to obtain a white solid, which is purified by silica gel column chromatography, using the volume of petroleum ether and acetone The eluent with a ratio of 2:1 was ...

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PUM

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Abstract

The invention discloses a compound and application thereof as an L-calcium channel retarder or / and an acetylcholinesterase inhibitor. The inhibition ratio of every 100 nmol / L of the compound to an L-calcium channel is 8.71-35.77 percent, and the inhibition ratio of every 1,000 nmol / L of the compound to the L-calcium channel is 26.43-83.54 percent. The IC50 of the compound to acetylcholinesterase activity is 16-1,470 nmol / L, which indicates that the compound has an effective retardation effect on the L-calcium channel and a remarkable inhibition effect on acetylcholinesterase. The invention further provides application of the compound to preparation of medicaments for treating cardiovascular diseases, apoplexy or senile dementia.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a compound and its application as an L-type calcium channel blocker or / and an acetylcholinesterase inhibitor. Background technique [0002] Alzheimer's disease is a degenerative disease of the central nervous system characterized by chronic, progressive cognitive impairment and memory impairment. The main pathological features are senile plaques, neurofibrillary tangles and neuron loss, which seriously affects patients. Cognition, memory, language function and personal life ability and emotional personality. At present, the more accepted pathology of Alzheimer's disease in the world is the "cholinergic deficiency theory". The theory is that the loss of the neurotransmitter choline acetate in the patient's brain is the key cause of Alzheimer's disease. [0003] Cholinesterase is a key enzyme in biological nerve transmission. In cholinergic synapses, this enzyme can degrade acet...

Claims

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Application Information

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IPC IPC(8): C07D211/90C07D401/04C07D401/12C07D401/14C07D413/14A61K31/4422A61K31/4439A61K31/473A61K31/496A61K31/4725A61K31/4545A61P3/14A61P9/00A61P9/10A61P25/28
CPCC07D413/14C07D211/90C07D401/12C07D401/04C07D401/14A61P3/14A61P9/00A61P9/10A61P25/28
Inventor 陈荣刘飞丛欣冯林李海岛董情理
Owner JIANGSU SIMCERE PHARMA
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