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3-Hydroxyprogesterone-21-(2',5'-dimethoxy)benzylidene-5-ene-20-one and preparation method and application thereof

A technology of dimethoxy and benzylidene, which is applied in the field of medicine and can solve unseen problems

Inactive Publication Date: 2013-01-02
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] So far, there is no report on the structure, preparation method and use of 3-hydroxy-pregna-21-(2′,5′-dimethoxy)benzylidene-5-en-20-one

Method used

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  • 3-Hydroxyprogesterone-21-(2',5'-dimethoxy)benzylidene-5-ene-20-one and preparation method and application thereof
  • 3-Hydroxyprogesterone-21-(2',5'-dimethoxy)benzylidene-5-ene-20-one and preparation method and application thereof
  • 3-Hydroxyprogesterone-21-(2',5'-dimethoxy)benzylidene-5-ene-20-one and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of the compound 3-hydroxyl-pregna-21-(2′,5′-dimethoxy)benzylidene-5-ene-20-one shown in embodiment 1 structural formula I

[0030]

[0031] Formula II-1 Structural Formula I

[0032] Dissolve 500mg of the compound of formula II-1 in 20ml of methanol, add 1.2 molar equivalents of 2,5-dimethoxybenzaldehyde and 100mg of potassium hydroxide at 0°C, stir for 24h, add 80ml of water, then add 10% HCl Neutralize to pH ~ 6, filter, wash the filtrate with water, and dry to obtain a yellow solid compound represented by structural formula I, with a yield of 90%. 1 H NMR (300MHz, CDCl 3 ): δ7.83(d, 1H), 7.07(d, 1H), 6.92-6.78(m, 3H), 5.34(d, 1H), 3.83(s, 3H), 3.78(s, 3H), 3.52( m, 1H), 0.98(s, 3H), 0.63(s, 3H). ESI-MS: 465.4 [M+H + ].

Embodiment 2

[0033] Example 2: In Vitro Pharmacological Test 1 (Effect of Compounds on Aβ-Induced SH-SY5Y Cell Injury)

[0034] Purpose:

[0035] Observation of the protective effect of 3-hydroxy-pregna-21-(2′,5′-dimethoxy)benzylidene-5-en-20-one on the damage of SH-SY5Y cells induced by Aβ

[0036] experimental method:

[0037] SH-SY5Y was purchased from the National Cell Bank of the United States, using MEM / F12 medium containing 10% fetal bovine serum, 100 U / ml penicillin, and 100 μg / ml streptomycin, at 37°C, 5% CO 2 Routine cultivation in a saturated humidity incubator. Take 2×10 4 The density of cells / well was seeded in a 96-well plate, and the experiment was performed after 24 hours of culture. Aβ treatment: replace with serum-free MEM / F12, add different concentrations of compounds (1-10 μM) shown in structural formula I at the same time, add Aβ with a final concentration of 10 μM after cultivating for 2 hours, continue culturing for 24 hours, then add MTT (final concentration ...

Embodiment 3

[0040] Embodiment 3: in vitro pharmacological test 2 (test compound is to H 2 o 2 inducing cell damage)

[0041] Purpose:

[0042] Observation of the effect of 3-hydroxy-pregna-21-(2′,5′-dimethoxy)benzylidene-5-en-20-one on H 2 o 2 Protective effect of induced SH-SY5Y cell injury

[0043] experimental method:

[0044] Place SH-SY5Y (ATCC) cells in 5% CO 2 cultured in a constant temperature incubator at 37°C. The culture medium was MEM / F12 (1:1), and 10% FBS was added. Change the culture medium every 3-4 days. When the cell fusion rate is about 80%, it is digested with 0.125% trypsin and passaged at a ratio of 1:2. Take the stably growing SH-SY5Y cells, and use 1×10 5 seed / ml density in 96-well plate, 100μl / well, in 5% CO 2 Incubate in a 37°C constant temperature incubator for about 24 hours. Replace with fresh culture medium, and divide the cells into normal control group, H 2 o 2 Injury model group, compound pretreatment group. The compound pretreatment group...

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Abstract

The present invention relates to a steroidal compound of 3-hydroxyprogesterone-21-(2',5'-dimethoxy)benzylidene-5-ene-20-one shown in structural formula I and preparation method thereof, a medicinal composition containing the compound, and the application of the compound in preparation of medicines for prevention and / or treatment of neurodegenerative diseases.

Description

technical field [0001] The present invention relates to the technical field of medicine, in particular to a steroidal compound 3-hydroxyl-pregna-21-(2′,5′-dimethoxy)benzylidene-5 shown in structural formula I -en-20-one, its preparation method, pharmaceutical composition containing the compound and its use in the preparation of medicines for preventing and / or treating neurodegenerative diseases. [0002] [0003] Structural Formula I Background technique [0004] Neurodegenerative diseases (ND) are a group of chronic, degenerative neurological diseases based on primary neuron degeneration. Such diseases mainly include Alzheimer's disease (Alzheimer's disease, AD), vascular dementia (vascular dementia, VaD), Parkinson's disease (Parkinson's, PD) and the like. With the increasing aging of the world's population, the incidence of neurodegenerative diseases is increasing, and the highest incidence is AD. Scientists pointed out that there will be 22 million AD patients in t...

Claims

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Application Information

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IPC IPC(8): C07J9/00A61K31/575A61P25/28A61P25/16
Inventor 郭跃伟章海燕江成世傅燕
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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