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Substituted aryl oxygen ethylpiperazine derivative, preparation method of substituted aryl oxygen ethylpiperazine derivative and application of substituted aryl oxygen ethylpiperazine derivative

A technology of aryloxyethylpiperazine and derivatives is applied in the field of substituted aryloxyethylpiperazine derivatives and their preparation, and the preparation of neuroprotective agents, which can solve the problems of low selectivity, poor oral bioavailability, Difficulty in crossing the blood-brain barrier

Active Publication Date: 2013-02-13
NANJING MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The second technical problem to be solved by the present invention is to disclose the application of the above-mentioned substituted aryloxyethylpiperazine derivatives as a neuroprotective agent in the treatment of ischemic stroke, so as to overcome the existing problems in the prior art of inducing hemorrhage, difficulty in Defects such as blood-brain barrier penetration, poor oral bioavailability, low selectivity and high neurobehavioral toxicity

Method used

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  • Substituted aryl oxygen ethylpiperazine derivative, preparation method of substituted aryl oxygen ethylpiperazine derivative and application of substituted aryl oxygen ethylpiperazine derivative
  • Substituted aryl oxygen ethylpiperazine derivative, preparation method of substituted aryl oxygen ethylpiperazine derivative and application of substituted aryl oxygen ethylpiperazine derivative
  • Substituted aryl oxygen ethylpiperazine derivative, preparation method of substituted aryl oxygen ethylpiperazine derivative and application of substituted aryl oxygen ethylpiperazine derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0041] 2-(2-Bromoethoxy)naphthalene

[0042] Add ethyl naphthol (14.4g, 0.10mol), 1,2-dibromoethane (13mL, 0.15mol), water (60mL) into the three-necked flask, stir and raise the temperature to reflux, and add 25%wt of hydroxide Sodium solution (24mL), dripped in about 30 minutes. After reflux for 10 hours, the reaction solution was cooled and separated into layers, and left to stand overnight, a large amount of solids precipitated out. After suction filtration, the filter cake was washed twice with water and recrystallized twice from absolute ethanol to obtain 13.4 g of white crystals with a yield of 54.3%. TLC showed a pure point.

Embodiment 2

[0044] 1-(2-Bromoethoxy)-4-methylbenzene

[0045] Add p-cresol (13g, 0.12mol), 1,2-dibromoethane (15.6mL, 0.18mol), and water (72mL) into a three-necked flask, stir and raise the temperature to reflux, and add 25%wt of hydroxide Sodium solution (28.8mL), dripped in about 45 minutes. After reflux for 10 hours, the reaction liquid was cooled and separated into layers, and stood overnight without solid precipitation. The liquid was separated, the organic layer was washed twice with 40 mL of water, dried over anhydrous magnesium sulfate, filtered with suction, and the organic solvent was distilled off to obtain a pale yellow clear oily liquid. Distilled under reduced pressure to collect a fraction at 108°C / 0.08mmHg, which was initially a clear colorless oily liquid and then solidified into a white solid. Finally, 8.2 g of white solid was obtained, with a yield of 34.2%, and TLC showed a pure point.

Embodiment 3

[0047] 1-(2-Bromoethoxy)-2-methylbenzene

[0048] Add o-cresol (13g, 0.12mol), 1,2-dibromoethane (15.6mL, 0.18mol), and water (72mL) into a three-necked flask, stir and raise the temperature to reflux, and dropwise add 25%wt of hydroxide Sodium solution (28.8mL), dripped in about 45 minutes. After reflux for 13 hours, the reaction liquid was cooled and separated into layers, and stood overnight without solid precipitation. Separate the liquid, dissolve the organic layer with 20mL of dichloromethane, wash with 30mL of 5%wt sodium hydroxide solution for three times, then wash with 30mL of water for three times, dry over anhydrous magnesium sulfate, filter with suction, evaporate the filtrate to remove the solvent, and obtain a light yellow and clear The oily liquid was 10.9g, the yield was 42.3%, and TLC showed a pure point.

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Abstract

Provided are a substituted aryl oxygen ethylpiperazine derivative, a preparation method of the substituted aryl oxygen ethylpiperazine derivative and application of the substituted aryl oxygen ethylpiperazine derivative. A compound is free alkali or salt with a compound of a structure in a general formula (I), the salt is one of hydrochloride, hydrobromide, sulfate, trifluoroacetic acid salt, tartrate, lactate or mesylate, wherein an Ar independently stands for aryl groups, substituted heterocyclic rings or substituted aryl groups, an R1 and an R2 are same or different, and the R1 and the R2 independently stand for H, halogen, alkyl, halogen substituted alkyl, nitro, amino, nitrile groups, hydroxyl, alkoxy, aralkyl oxygroup, heterocyclic ring alkoxy, aryl group, the substituted heterocyclic rings or the substituted aryl groups respectively. The substituted aryl oxygen ethylpiperazine derivative is applied to preparation of cerebral arterial thrombosis therapeutic drugs.

Description

technical field [0001] The invention belongs to the field of pharmacy, and relates to a substituted aryloxyethylpiperazine derivative, a preparation method thereof, and an application of the derivative in preparing a brain neuroprotective agent. Background technique [0002] Stroke is one of the diseases with the highest mortality and disability rate today, and nearly 80% of strokes are ischemic strokes. The survival of brain cells after a stroke depends on how much neurons are damaged, that is, how much blood flow to the brain that supplies cells with oxygen and nutrients is reduced. When ischemic stroke occurs, the cerebral blood flow in the ischemic core is severely reduced, and irreversible damage occurs to the brain tissue after 60-90 minutes; while the cerebral blood flow in the peripheral ischemic penumbra of the core is relatively reduced, but the cell metabolism Within a few hours after the occurrence of ischemia, the abnormal electrical activity and metabolic diso...

Claims

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Application Information

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IPC IPC(8): C07D295/155C07D295/084C07D295/096A61K31/495A61P9/10A61P25/00
Inventor 吴斌戴兆慧王晶许逸李萍张晓平
Owner NANJING MEDICAL UNIV
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