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Baicalein derivatives and preparation method and application thereof

A technology of baicalein and derivatives is applied in the application field of prevention and treatment of chronic obstructive pulmonary emphysema, and achieves the effects of low cost, low price and good application prospect

Inactive Publication Date: 2011-07-13
SICHUAN DIHON MEDICAL DEV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it has not been seen that baicalin is used as a source, and its structure is modified to obtain a strong anti-COPD baicalein derivative

Method used

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  • Baicalein derivatives and preparation method and application thereof
  • Baicalein derivatives and preparation method and application thereof
  • Baicalein derivatives and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 16

[0032] The preparation of embodiment 16-benzyloxybaicalein

[0033]

[0034] Dissolve 13.38g (30mg) baicalin in 50ml DMF, add anhydrous K 2 CO 3 20.76g (150mmol), 3.56ml (30mmol) of benzyl bromide, and 300ml of anhydrous acetone were placed in a 500ml reaction bottle, and refluxed in a dry state until the reaction was complete, then filtered while hot. After the filtrate was evaporated to dryness under reduced pressure, adjust the pH to 5 with 10% acetic acid solution, collect the solid, add 200ml of ethanol and 20ml of concentrated HCl into a 500ml reaction bottle, reflux until the reaction is complete, evaporate the solvent under reduced pressure, and wash the impurities with water. After that, use CH 2 Cl 2 -EtOH was repeatedly recrystallized to obtain 5.69g, and the total yield of the two steps was 52.6%.

[0035] 1 H-NMR (600MHz, DMSO): δ8.04 (2H, m), 7.52-7.61 (3H, m), 7.43 (4H, m), 7.35 (1H, m), 6.87 (1H, s), 6.62 ( 1H, s), 4.82 (2H, s); ESI-MS m / z: 361 [M+H] ...

Embodiment 26

[0036] The preparation of embodiment 26-n-butoxybaicalein

[0037]

[0038] Dissolve 4.46g (10mmol) baicalin in 25ml DMF, add anhydrous K 2 CO 36.92g (50mmol), 1.07ml (10mmol) of 1-bromo-n-butane, 150ml of anhydrous acetone, placed in a 250ml reaction flask, refluxed in a dry state, until the reaction was complete, filtered, evaporated to dryness, and dissolved in 10% The acetic acid solution adjusted the pH to 5, collected the solid, added to a 250ml reaction flask containing 150ml of ethanol and 10ml of concentrated HCl, refluxed until the reaction was complete, filtered, and column chromatographed to obtain 1.57g of a light yellow solid, with a yield of 48.1%.

[0039] 1 H-NMR (600MHz, DMSO): δ8.04 (2H, m), 7.54-7.60 (3H, m), 6.93 (1H, s), 6.61 (1H, s), 3.94 (2H, m), 1.66 ( 2H, m), 1.44 (2H, m), 0.89 (3H, m); ESI-MS m / z: 327 [M+H] + , 349[M+Na] + (pos i t ive mode).

Embodiment 36

[0040] The preparation of embodiment 36-allyloxybaicalein

[0041]

[0042] Dissolve 4.46g (10mmol) baicalin in 25ml DMF, add anhydrous K 2 CO 3 6.92g (50mmol), 0.86ml (10mmol) of allyl bromide, 150ml of anhydrous acetone, placed in a 250ml reaction bottle, refluxed in a dry state, until the reaction was complete, filtered while hot, evaporated to dryness, and dissolved in 10% acetic acid The pH of the solution was adjusted to 5, the solid was collected, added to a 250ml reaction bottle containing 150ml of ethanol and 10ml of concentrated HCl, refluxed until the reaction was complete, filtered, and column chromatography gave 1.74g of a light yellow solid, with a yield of 56.2%.

[0043] 1 H-NMR (600MHz, DMSO): δ8.06(2H, m), 7.55-7.62(3H, m), 7.01(1H, s), 6.95(1H, s), 6.03(1H, m), 5.17( 1H, m), 5.29 (1H, m), 4.48 (2H, m); ESI-MS m / z: 311 [M+H] + , 333[M+Na] + (positive mode).

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Abstract

The invention discloses a kind of baicalein derivatives and a preparation method and application thereof. Pharmacological tests prove that the compounds have the obvious function of dilating bronchi and can be used to prepare the medicines used for preventing or curing chronic obstructive emphysema caused by bronchial constriction.

Description

technical field [0001] The present invention relates to a class of baicalein derivatives with bronchodilating activity and the application of the compounds as active pharmaceutical ingredients in the prevention and treatment of chronic obstructive emphysema. Background technique [0002] Chronic obstructive pulmonary disease (COPD), referred to as COPD, is a disease characterized by airway airflow limitation, including chronic bronchitis and emphysema. This airflow limitation is usually progressive, not fully reversible, and can be accompanied by airway hyperresponsiveness. In the United States and even in the world, COPD is the fourth leading cause of death, second only to heart disease, cerebrovascular disease and acute respiratory infection. According to the survey conducted by the Asia-Pacific Respiratory Society, the prevalence rate of COPD in 11 Asian countries is 6.2%. Spot checks in some areas of my country show that the incidence rate of people over the age of 15 i...

Claims

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Application Information

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IPC IPC(8): C07D311/30C07D493/04A61K31/352A61K31/36A61K31/357A61P11/00A61P11/08
Inventor 余红伟龙绍疆马燕如朱绪明周宁李蕾蕾梁勇陈秀权陈逢春官敬博
Owner SICHUAN DIHON MEDICAL DEV
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