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Phenoxy indenone compounds, process for preparing same and use thereof

A technology for phenoxyindanone and compounds, which is applied in the field of synthesis of phenoxyindanone derivatives, can solve problems such as no structure-activity relationship and different structures, and achieve delay in hydrolysis, simple preparation, and wide source of raw materials Effect

Inactive Publication Date: 2006-04-19
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] At present, acetylcholinesterase inhibitors (AchEI) are the most effective clinical medicines for the treatment of senile dementia and have the widest range of clinical applications. Such drugs include Tacrine, Donepezil, and Galanthamine. , rivastigmine (Rivastigmine) and huperzine A (Huprine), etc., there are still dozens of drugs in preclinical or clinical research, from the current research analysis, the structures of these inhibitors are different, there is no Clear structure-activity relationship

Method used

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  • Phenoxy indenone compounds, process for preparing same and use thereof
  • Phenoxy indenone compounds, process for preparing same and use thereof
  • Phenoxy indenone compounds, process for preparing same and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Preparation of 2-bromo-5,6-dimethoxy-1-indanone (III)

[0034] 3.84g (0.02mol) of 5,6-dimethoxyindanone (II) was dissolved in 20mL of chloroform, the temperature was raised to reflux, 4.93g of copper bromide was added in batches, and the reaction was continued for 3 hours. Cool in an ice bath, remove the solid by suction filtration, and wash with 20ml×2 chloroform, combine the filtrates, and successively wash with saturated NaHCO 3 , saturated NaCl solution washing, anhydrous Na 2 SO 4 After drying, the solvent was recovered under reduced pressure to obtain a yellow solid, which was recrystallized from ethanol to obtain 4.62 g of a white solid, m.p.=184-186°C.

Embodiment 2

[0035] Example 2: Preparation of 2-bromo-5,6-dimethoxy-1-indanone (III)

[0036] 3.84g (0.02mol) 5,6-dimethoxyindanone (II) was dissolved in 30ml THF, and 7.68g (0.024mol) pyridine perbromide was added in batches within 3 hours at room temperature, and then the reaction was continued for 2 Hour. Cool in an ice bath, remove the solid by suction filtration, wash with THF 20ml×2, combine the filtrates, recover the solvent under reduced pressure, add 30ml of dichloromethane and 10ml of water to the residue, separate the organic layer, and wash with saturated NaHCO 3 , saturated NaCl solution washing, anhydrous Na 2 SO 4 After drying, the solvent was recovered to obtain a crude product, which was recrystallized from ethanol to obtain 4.36 g of a white solid.

Embodiment 3

[0037] Embodiment 3: the preparation of 1-[(3-hydroxyphenyl) methyl] piperidine

[0038] Dissolve 2.44g (0.02mol) of 3-hydroxybenzaldehyde in 20ml of methanol, add dropwise a mixed solution of 4.4ml of piperidine and 5ml of methanol at room temperature, and continue the reaction for 30 minutes after the addition; Add 0.53gKBH 1, continue to react for 1 hour after adding. Cool in an ice bath, adjust the pH to 2 with 2N hydrochloric acid, recover the solvent, add 30ml of 2N hydrochloric acid and 15ml of ethyl acetate to the residue, separate the organic layer and discard it; adjust the pH of the aqueous layer to 10 with concentrated ammonia, add 20ml of ethyl acetate ×3 extraction, combined organic layers, washed with saturated NaCl, anhydrous Na 2 SO 1 After drying, the solvent was recovered to obtain a crude product, which was recrystallized from ethanol-water to obtain 3.42 g of white granular crystals, with a yield of 89.5%, m.p.136-138°C.

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Abstract

The present invention provides one kind of phenoxy indenone compound. Pharmacological experiment shows that the compound may be used as acetylcholinesterase inhibitor and can competitively inhibit the activity of acetylcholine, delay the hydrolysis of acetylcholine and thus raise the synapse effect of acetylcholine. The compound may be used in preparing medicine for treating presenile dementia. The present invention has easy to obtain material, has mild reaction condition, high yield, simple operation and low production cost, and is suitable for industrial production.

Description

Technical field [0001] The present invention relates to the synthesis and application of phenoxyindanone derivatives. Background technique [0002] Alzheimer's disease is a neurodegenerative disease whose etiology has not been conclusively described so far. Because of its high incidence in the elderly, it seriously threatens the health of the elderly, and the aging of the population in today's society is becoming more and more obvious. Therefore, the study of drugs for the treatment of AD has become one of the hot spots of new drug research. [0003] The current drug research on senile dementia mainly includes the following aspects: [0004] 1. Acetylcholinesterase inhibitor (AchEI), which can inhibit the hydrolysis of acetylcholine by acetylcholinesterase, prolong the retention time of acetylcholine in the brain, thereby prolonging its effect on choline receptors in the brain, and improving the choline nerve function of AD patients. function, reduce the decline of the pat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/03A61K31/4453A61K31/495A61K31/535A61P25/28
Inventor 盛荣胡永洲陈忠徐利莎
Owner ZHEJIANG UNIV
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