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Chrysin and substituted salicylate composites, manufacturing method thereof and use thereof

A technology of salicylate and chrysin, which is applied to a class of chrysin and substituted salicylate complexes and the fields of their preparation and use, and can solve problems such as easy side effects and the like

Inactive Publication Date: 2012-02-29
南京大学中国医药城研发中心
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, long-term large-scale medication (such as treatment of rheumatic fever), especially when the blood concentration of the drug is greater than 200 μg / mL, side effects are more likely to occur

Method used

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  • Chrysin and substituted salicylate composites, manufacturing method thereof and use thereof
  • Chrysin and substituted salicylate composites, manufacturing method thereof and use thereof
  • Chrysin and substituted salicylate composites, manufacturing method thereof and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Preparation of ethyl 2-(5-hydroxy-2-phenyl-4H-benzopyrone-7-oxo)acetate

[0021]

[0022] Chrysin (2.54g, 10mmol) and anhydrous potassium carbonate (2.76g, 20mmol) were sequentially added to anhydrous acetone, then ethyl bromoacetate (0.3ml, 15mmol) was added dropwise, and heated to reflux at 60°C for 12h. After complete cooling, filter under vacuum, discard the solids to obtain the filtrate, wash with water (100ml) and then wash with sodium hydroxide solution (10%, 100ml), and finally wash with water (100ml) again, and after drying, obtain the target compound. Pale yellow solid, yield 86%, mp: 243-245°C, 1 H NMR (300MHz, d 6 -DMSO): 1.25(t, J=6.9Hz, 3H); 4.19(m, 2H); 4.96(s, 2H); 6.43(m, 1H); 6.85(m, 1H), 7.01(s, 1H) , 7.60 (m, 3H), 8.10 (m, 2H), 12.81 (s, 1H). MS (ESI): 340.1 (C 19 h 16 o 6 ,[M+H] + ).Anal.Calcd for C 19 h 16 o 6 : C, 67.05; H, 4.74%; Found: C, 67.08; H, 4.72%.

Embodiment 2

[0023] Example 2: Preparation of 2-(5-hydroxyl-2-phenyl-4H-benzopyrone-7-oxo)acetic acid

[0024]

[0025] The product 2-(5-hydroxy-2-phenyl-4H-benzopyrone-7-oxo)ethyl acetate (3.4g, 10mmol) obtained in Example 1 was dissolved in dimethyl sulfoxide (DMSO) After completely dissolving in the solution, add 40ml of 5% sodium carbonate aqueous solution, and heat to reflux at 90°C for 8h. After the reactants were completely reacted, 50ml of 1M hydrochloric acid solution was added, stirred continuously, and allowed to stand for 4h, and a yellow solid was precipitated. After washing with water (100ml) twice, and drying, the title compound was obtained as a yellow solid. Yield 82%, mp: 315-316°C; 1 H NMR (500MHz, d 6 -DMSO): 2.51 (s, 3H); 4.85 (s, 2H); 6.41 (m, 1H), 6.82 (m, 1H); 7.04 (s, 1H); 7.61 (m, 3H), 8.11 (m, 2H), 12.80(s, 1H), 13.20(s, 1H). MS (ESI): 312.1 (C 17 h 12 o 6 ,[M+H] + ).Anal.Calcd for C 17 h 12 o 6 : C, 65.39; H, 3.87%; Found: C, 65.37; H, 3.85%.

Embodiment 3

[0026] Example 3: Preparation of 5-hydroxy-2-[2-(5-hydroxy-2-phenyl-4H-benzopyrone-7-oxo)acetoxy]-benzoic acid methyl ester (compound 1) .

[0027]

[0028]The product 2-(5-hydroxyl-2-phenyl-4H-benzopyrone-7-oxo)acetic acid (3.12g, 10mmol) obtained in Example 2 was dissolved in 30ml N,N-dimethylformaldehyde amide (DMF), then added 5-hydroxymethylsalicylate (1.68g, 10mmol), N,N-dimethylaminopyridine (DMAP) (61mg, 2.03mmol) and N,N-dicyclohexyl carbon Diimine (DCC) (3.08g, 11mmol) was heated to reflux at 95°C for 12h. After the reaction was complete, it was extracted with ethyl acetate, and the organic layer was washed with saturated brine, and then washed with anhydrous Na 2 SO 4 After drying, the solvent is evaporated to dryness under reduced pressure and separated with a silica gel column. The eluent is: ethyl acetate: sherwood oil = 1: 2-1: 5 to obtain the above-mentioned chrysin and 5-hydroxysalicylate complex of the present invention . White powder. The yield was ...

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Abstract

The invention discloses novel chrysin and substituted salicylate composites having a general formula below. In the formula, R1 represents CH3 or CH2CH3, R2 represents H and OCH3, R3 represents H, Cl, Br or CH3, and R4 represents H, F, Cl, Br, OH or CH3. The novel chrysin and substituted salicylate composites of the invention have an obvious inhibiting effect on mouse lymphocyte proliferation caused by ConA. In the invention, compounds with high activity are screened out to be used in tests on mouse lymphocyte proliferation caused by anti-CD3 and anti-CD28 antibodies, and the results of the tests show that the compounds can inhibit the mouse lymphocyte proliferation caused by the anti-CD3 and anti-CD28 antibodies in a dose-dependent manner and have the same inhibiting effect with a cyclosporin A positive medicament. Therefore, the compounds are potential nonsteroidal antiinflammatory drugs. The invention discloses a method for preparing the novel chrysin and substituted salicylate composites.

Description

technical field [0001] The present invention relates to a novel compound of chrysin and substituted salicylate (also known as: 2-[2-(5-hydroxyl-2-phenyl-4H-benzopyrone-7-oxygen) acetoxy ] substituted benzoate) and its preparation method and use. Background technique [0002] Salicylates, as an anti-inflammatory drug, can be traced back to the ancient culture of the Asyrian Empire, where the Assyrians used willow leaf extract to treat vascular and muscular pain diseases. Salicylates were the first (1875) drugs to treat rheumatism and gout. In view of the gastrointestinal irritation and unpleasant taste of salicylate, in 1897, Hoffman, a chemist from Bayer Company in Germany, successfully synthesized aspirin-acetylsalicylic acid (ASA). So far, aspirin has been used for a hundred years and has become one of the three classic drugs in the history of medicine. It is still the most widely used antipyretic, analgesic and anti-inflammatory drug in the world, and it is also used as...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/30A61K31/625A61P29/00
Inventor 朱海亮吕鹏程王开锐陈进毛文君
Owner 南京大学中国医药城研发中心
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