3-substituted benzene phthalein compounds with biological activity

A compound and phthalide technology, applied in the field of 3-substituted phthalide compounds, can solve problems such as no effective treatment yet

Inactive Publication Date: 2009-04-08
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are currently no treatments that speci

Method used

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  • 3-substituted benzene phthalein compounds with biological activity
  • 3-substituted benzene phthalein compounds with biological activity
  • 3-substituted benzene phthalein compounds with biological activity

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Experimental program
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Effect test

Embodiment 13

[0021] Preparation of embodiment 13-substituted phthalides:

[0022]The 3-substituted phthalides involved in the present invention can be prepared according to the following two methods, wherein method one is used to prepare chiral novel 3-substituted phthalides, and method two is used to prepare racemic novel 3-substituted phthalides.

[0023] Method 1: From room temperature to 80°C, with a substrate concentration of 0.5-1.25 mol / L, in 2-5 equivalents of reducing agent formate, chiral diamine ligand and (p-methylisopropyl)phenyl dichloride Under the catalysis of the complex catalyst of ruthenium dimer, the number of moles of the substrate and the number of moles of the catalyst are 100-500:1, react for 4-24 hours, and purify by column chromatography to obtain a certain yield and a certain optical purity Product; General reaction formula is as follows:

[0024]

[0025] Among them, the main configuration of the product is determined by the configuration of the chiral liga...

Embodiment 2

[0037] Embodiment 2 biological experiments:

[0038] 1. Drosophila training and learning index measurement operation of olfactory short-term memory deficit test:

[0039] About 100 fruit flies were placed in an automatic training device for training. During the training, two gases 1.5‰ octanol and 1‰ methylcyclohexanol were introduced successively, one with electric shock CS+ and the other without electric shock CS-, 1 Their memory was tested immediately after the period training ended. During the detection, the fruit flies were placed in the center of two opposite smells, and allowed to choose freely for 120 seconds, and the learning index was calculated according to the number of fruit flies that chose each smell.

[0040] 2. Drosophila training and learning index measurement operation of the olfactory long-term memory deficit test:

[0041] About 100 fruit flies were trained in an automatic training device. During the training, two gases 1.5‰ octanol and 1‰ methylcyclohex...

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PUM

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Abstract

The invention provides 3-substituent phthalide compounds first. The constitutional formula of the compounds is shown in the right. The compounds are sifted through a drosophila study ability model to find that most of the compounds play the role of restoring study ability on defected individuals; and specific compounds thereof express better activities, allow the defected individuals to restore over 85 percent of study ability and play the role of stable treatment in multiple rounds of experiments. Based on the experiments, the novel 3-substituent phthalide compounds are bioactive molecules for treating Alzheimer's disease.

Description

technical field [0001] The invention relates to a series of biologically active 3-substituted phthalide compounds. Background technique [0002] Alzheimer's disease, also known as Alzheimer's disease (Alzheimer's disease, AD) is a kind of primary degenerative brain disease that occurs in old age and early old age, and refers to a kind of persistent high-level neurological dysfunction, that is, in the Obstacles in memory, thinking, analysis and judgment, visuospatial recognition, emotions, etc. without disturbance of consciousness. Its characteristic pathological changes are atrophy of the cerebral cortex, accompanied by deposition of β-amyloid (β-AP), neurofibrillary tangles (neurofibrillary tangles, NFT), a large number of memory neurons decreased, and The formation of senile plaques (senileplaque, SP). There are currently no therapeutic drugs that can specifically treat or reverse disease progression. [0003] With the development of society, the speed of population agi...

Claims

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Application Information

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IPC IPC(8): C07D307/88C07D409/06C07D491/048C07D405/06C07D405/04C07D407/04A61K31/343A61K31/381A61K31/436A61K31/4709A61K31/357A61P25/28
Inventor 林国强陈雯雯张波孙兴文冯陈国徐明华
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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