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Medical use of beta-(3,4-dihydroxy phenyl)-alpha-hydroxy propionic ester compounds

A technology of polyphenolic compounds and compounds, which is applied in the field of β-α-hydroxypropionate compounds, can solve the problems of salvia miltiorrhiza compounds, and achieve the effects of preventing Aβ aggregation, promoting the proliferation of neural stem cells, and promoting the degradation of Aβ

Inactive Publication Date: 2009-07-08
BEIJING NORMAL UNIVERSITY
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  • Summary
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Salvia miltiorrhiza is traditionally a traditional Chinese medicine used solely for the treatment of cardiovascular diseases, and it is also one of the main active ingredients of many traditional Chinese medicines or Chinese herbal extracts used for the prevention and / or treatment of cardiovascular diseases, but Danshen compounds do not easily pass through the blood-brain barrier

Method used

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  • Medical use of beta-(3,4-dihydroxy phenyl)-alpha-hydroxy propionic ester compounds
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  • Medical use of beta-(3,4-dihydroxy phenyl)-alpha-hydroxy propionic ester compounds

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Experimental program
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Effect test

preparation example 1

[0064] Compound Preparation Example 1: Preparation of β-(3,4-Dihydroxyphenyl)-α-Hydroxybornyl Propionate (Compound 1)

[0065] 0.12mol of β-(3,4-dihydroxyphenyl)-α-hydroxypropionic acid (extracted in this laboratory, purity 96%) and 0.18mol of borneol were added to 500ml of tetrahydrofuran, and the catalyst p-toluenesulfonic acid 0.86 g, reacted at 65°C for 8h. After the reaction, the catalyst, solvent and unreacted borneol were removed to obtain a brown viscous substance, which was separated by column chromatography to obtain a pale yellow oil (compound 1).

[0066] IR v(liquid paraffin)cm -1 : 3320, 2955, 2915, 1810, 1596, 1519, 1450, 1280, 1113, 885, 801.

[0067] ESI+: 335

[0068] 1 H NMR see figure 1 (1).

preparation example 2

[0069] Compound Preparation Example 2: Preparation of β-(3,4-dihydroxyphenyl)-α-hydroxypropionic acid isopropyl ester (compound 2)

[0070]

[0071] Compound 2

[0072] According to the above reaction process, 0.1 mol of compound a and 0.1 mol of compound b were dissolved in water, reacted at room temperature for 4 hours, and c was isolated. c was reacted with sodium acetate and 3,4-dihydroxybenzaldehyde according to 1:1.2:1.5 at 100°C for 30min, and d was separated. d first reacted with zinc-amalgam concentrated hydrochloric acid for 7 hours under reflux, then added sodium bicarbonate to adjust the pH value to about 5, and e was precipitated. e reacts with isopropanol at room temperature according to 1:1.2 to generate the target product compound 2.

[0073] ESI+: 241

[0074] 1 H NMR see figure 1 (2).

preparation example 3

[0075] Compound Preparation Example 3: Preparation of β-(3,4-dihydroxyphenyl)-α-hydroxypropionate catechin prepare (compound 3)

[0076] According to conventional ester-forming method, select relatively mild condition, 0.1mol salvia miltiorrhiza (extracted in this laboratory, purity 96.8%) and 0.18mol catechin are dissolved in 200ml benzene, add catalyst p-toluenesulfonic acid 0.86g, Reaction at room temperature for 12h. After the reaction, the catalyst, solvent and unreacted catechin were removed to obtain compound 3.

[0077] ESI+: 471

[0078] 1 H NMR see figure 1 (3).

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Abstract

The invention provides beta-(3, 4-dihydroxy benzene)-alpha-hydroxyl propionate compounds in a formula (I). The invention also relates to application of the beta-(3, 4-dihydroxy benzene)-alpha-hydroxyl propionate compounds in the formula (I) in preparing medicines for preventing A beta aggregation and / or promoting degradation of aggregated A beta, promoting proliferation of neural stem cells, and treating, preventing and / or delaying neurodegenerative diseases. The beta-(3, 4-dihydroxy benzene)-alpha-hydroxyl propionate compounds in the formula (I) can effectively treat related diseases.

Description

technical field [0001] The present invention relates to a class of β-(3,4-dihydroxyphenyl)-α-hydroxypropionate compounds, and the present invention also relates to β-(3,4-dihydroxyphenyl)-α-hydroxypropionate Use of compounds of the same type in the preparation of medicines for treating, preventing and / or delaying neurodegenerative diseases and related diseases. Background technique [0002] Neurodegenerative disease is a complex multifactorial chronic progressive mental degenerative disease characterized by damage and degeneration of nerve cells. Neurodegenerative diseases include Alzheimer's disease (AD), Parkinson's disease (PD) , Huntington's disease (HD), multiple sclerosis (MS), etc. The clinical manifestation is degeneration of nerve cells, which leads to the loss of brain cell function and causes a variety of brain diseases. Neurodegenerative diseases seriously endanger human health and quality of life, causing great burden and pressure to patients' families and soc...

Claims

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Application Information

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IPC IPC(8): C07C69/732C07D311/62A61K31/216A61K31/353A61P25/00A61P25/14A61P25/16A61P25/28
Inventor 韩梅赵长崎王永炎
Owner BEIJING NORMAL UNIVERSITY
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