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Scutellarein derivative, its preparing process and application

A kind of technology of baicalein and derivatives, applied in the field of baicalein derivatives

Inactive Publication Date: 2007-07-04
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

However, there is no literature report on the structural modification of baicalein to obtain a stronger anti-lipid peroxidation effect and prevent and treat diseases caused by free radical damage.

Method used

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  • Scutellarein derivative, its preparing process and application
  • Scutellarein derivative, its preparing process and application
  • Scutellarein derivative, its preparing process and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] The preparation of embodiment 1 7-n-hexyloxybaicalein

[0058] 1-a: 5, 6, 7-triacetoxy baicalein Put 5.40g (20mmol) baicalein, 31.8mL (300mmol) acetic anhydride, 2.25g (28.0mmol) anhydrous sodium acetate in a 100mL reaction flask, React at 80°C until there is no raw material, pour it into 150mL of ice water, precipitate a gray solid, collect it by filtration, wash away impurities with ethanol, and obtain 7.21g of an off-white solid, with a yield of 91.1%.

[0059] 1 HNMR (400MHz, CDCl 3 ): δ2.35(s, 3H), 2.36(s, 3H), 2.45(s, 3H), 6.66(s, 1H), 7.51-7.55(m, 4H), 7.85-7.87(m, 2H); MS (EI): m / z 396 (M + ), 354, 312, 270 (100%)

[0060] 1-b: 5,6-diacetyl-7-allyloxybaicalein 3.96g (10mmol) 5,6,7-triacetoxybaicalein, anhydrous K 2 CO 3 5.52g (40mmol), 2.54mL (30mmol) of allyl bromide, 250mL of anhydrous acetone, placed in a 500mL reaction bottle, refluxed in a dry state until the reaction was complete, filtered while hot, and evaporated to dryness to obtain an off-white ...

Embodiment 2

[0073] The preparation of embodiment 2 7-hexadecyloxybaicalein

[0074] 2-a: 5,6-dibenzyloxy-7-hexadecyloxybaicalein 0.121g (0.269mmol) 5,6-dibenzyloxybaicalein, 0.133g (1.25mmol) anhydrous Na 2 CO 3 , 0.458mL (1.50mmol) 1-Bromohexadecane, 65mL of anhydrous acetone, 5mL of anhydrous DMF, placed in a 100mL reaction bottle, refluxed in a dry state, reacted until no raw materials were present, filtered, purified by column, and purified with ethyl acetate and petroleum ether The mixture was eluted to obtain 0.152g white solid, yield 83.9%

[0075] 1 HNMR (400MHz, CDCl 3 ): δ0.86-0.90(m, 3H), 1.18-1.57(m, 26H), 1.87-1.94(m, 2H), 4.08(t, 2H), 5.05(s, 2H), 5.15(s, 2H ), 6.70(s, 1H), 6.84(s, 1H), 7.32-7.41(m, 6H), 7.45-7.54(m, 5H), 7.68-7.70(m, 2H), 7.88-7.90(m, 2H ); MS (EI) m / z: 674 (M + ), 583 (100%), 493, 359, 269, 91;

[0076] 2-b: 7-hexadecyloxybaicalein 0.150g (0.222mmol) 5,6-dibenzyloxy-7-hexadecyloxybaicalein, 10% Pd / C 75mg, THF 60mL, put 100mL reaction flask, in H 2...

Embodiment 3

[0078] The preparation of embodiment 3 7-(4'-methoxy)benzyloxy baicalein

[0079] 3-a: 5,6-diacetyl-7-(4`-methoxy)benzyloxybaicalein 0.277g (0.70mmol) 5,6,7-triacetoxybaicalein, 0.483g ( 3.50mmol) anhydrous K 2 CO 3 , 0.24mL (1.75mmol) 4-methoxybenzyl chloride, 0.015g (0.09mmol) KI, 40mL of anhydrous acetone, reflux in a dry state until the reaction is complete, filter while hot, and evaporate to dryness to obtain an off-white solid. Impurities were washed with ethyl acetate to obtain 0.269 g of white solid, yield 81.0%.

[0080] 1 HNMR (400MHz, CDCl 3 ): δ2.28(s, 3H), 2.45(s, 3H), 3.82(s, 3H), 5.12(s, 2H), 6.60(s, 1H), 6.92-6.94(m, 2H), 7.01( s, 1H), 7.32-7.34 (d, 2H), 7.49-7.54 (m, 3H), 7.83-7.85 (m, 2H); MS (EI) m / z: 474 (M + ), 432, 390, 270, 121 (100%), 84;

[0081] 3-b: 7-(4`-methoxy)benzyloxybaicalein: 0.160g (0.338mmol) 5,6-diacetyl-7-(4-methoxy)phenoxybaicalein, 2mL 5% NaOH, 30mL acetone, in N 2 Under gas protection, react at 40-50°C until complete, adjust th...

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Abstract

The invention discloses a novel scutellarein derivative, the method for preparing the same and the application. It is proved through pharmacological test that the compound possesses obvious effect against lipid peroxidation, effect against cell damage induced by H2O2 and cell apoptosis induced by A beta, it can also inhibit Cu2+ from inducing oxidation and modification for low density lipoprotein. The compound can be used to prepare medicine that can prevent or treat neurodegenerative diseases such as Alzheimer's disease caused by free radical oxidation, and medicine that can treat inflammation, reduce blood fat and treat atherosclerosis.

Description

technical field [0001] The present invention relates to a class of novel baicalein derivatives, in particular to the application of a class of drugs for treating neurodegenerative diseases such as Alzheimer's disease, anti-inflammation, lowering blood fat and treating atherosclerosis. Background technique [0002] Free radicals are closely related to diseases. When the production and removal of free radicals in the body are out of balance, excessive free radicals will cause damage to DNA, sugars, proteins and lipids, thereby causing a series of diseases such as aging, cardiovascular diseases, etc. Compounds of oxidative nature are likely to be effective in the prevention and treatment of these diseases. Searching for and screening drugs that can block free radical formation or scavenge free radicals has attracted more and more attention. [0003] Baicalein is a main active ingredient of Scutellaria baicalensis, a traditional Chinese medicine, which has various physiologica...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30A61K31/352A61P25/00A61P29/00A61P3/06A61P9/10
Inventor 沈竞康丁德荣张福军王蕊傅燕龚邦强王逸平蔡茂军马兰萍李欣
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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