Scutellarin aglycone methylate product based on in-vivo metabolic mechanism as well as preparation method and application of scutellarin aglycone methylate product

A technology of scutellarin aglycon methyl and scutellarin aglycone, which is applied in the field of medicinal chemistry research and can solve the problem of low adverse reactions

Inactive Publication Date: 2012-10-03
NANJING UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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Problems solved by technology

[0005] Purpose of the invention: The technical problem to be solved by the present invention is to overcome the deficiencies of the prior art and use scutellarin glycosides as raw materials to undergo glycoside hydrolysis, selective protection and deprotection, and selective methylation to synthesize a series of medicinal value And ...

Method used

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  • Scutellarin aglycone methylate product based on in-vivo metabolic mechanism as well as preparation method and application of scutellarin aglycone methylate product
  • Scutellarin aglycone methylate product based on in-vivo metabolic mechanism as well as preparation method and application of scutellarin aglycone methylate product
  • Scutellarin aglycone methylate product based on in-vivo metabolic mechanism as well as preparation method and application of scutellarin aglycone methylate product

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 15

[0120] Example 15, Preparation of 6,7-trihydroxy-2-(4-methoxyphenyl)-4H-chromone (I-1)

[0121] (1) Preparation of 5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromone (2)

[0122] Take scutellarin (1) (5g, 10.82mmol) and add to 3mol L -1 In 50mL of 90% concentrated sulfuric acid ethanol solution, 120°C with N 2 Protect the reaction for 48 hours, cool down after the reaction, pour the reaction solution into 8 times the amount of water, filter with suction, wash the filter cake with water until neutral, and dry at 50°C. The filter cake was repeatedly recrystallized with 80% and 50% ethanol to obtain 2 crude product. 2 The crude product was separated by silica gel column chromatography (dichloromethane:methanol=60:1) to obtain 790mg of the product. Yellow powder, yield 25.5%. 1 H NMR (300MHz, DMSO-d 6 )δ: 12.79(s,1H,5-OH);10.44(s,1H,7-OH);10.30(s,1H,4′-OH);8.71(s,1H,6-OH);7.90- 7.93(d,2H,J=8.8Hz,2′,6′-H);6.90-6.93(d,2H,J=8.8Hz,3′,5′-H);6.73(s,1H,8- H); 6.78(s,1H,3-H). ESI-MS...

Embodiment 26

[0129] Example 26, Preparation of 7-dihydroxy-5-methoxy,-2-phenyl-4H-chromone (I-2)

[0130] (1) 6,7-dimethoxymethyleneoxy-5-hydroxy-2-(4′-methoxymethyleneoxyphenyl)-4H-1-benzopyran-4-one ( 5) Preparation

[0131] Take (2g, 7mmol) 2 and put it into 100mL of dry acetone, heat it to fully dissolve. Add (3.87g, 28mmol, 4equiv) K under ice bath and nitrogen protection 2 CO 3 , reacted for 30 minutes under ice bath and nitrogen protection, then added (2.39 mL, 31.5 mmol, 4.5 equiv) MOMCl, reacted at room temperature for 1 hour, and then refluxed for 4 hours. The reaction solution was suction filtered, the filter cake was washed with acetone, and the combined filtrates were concentrated. Separation and purification by silica gel column chromatography, eluent petroleum ether: ethyl acetate (4:1). 2.31 g of (5) was obtained as a yellow solid with a yield of 79%. 1 H NMR 300MHz, DMSO-d 6 )δ: 12.93(s,1H,5-OH);8.05-8.08(d,2H,J=8.7Hz,2′,6′-H);7.14-7.17(d,2H,J=8.7Hz,3 ′,5′-H);7.09(...

Embodiment 35

[0136] Example 35, Preparation of 7-dihydroxy-6-methoxy-2-phenyl-4H-chromone (I-3)

[0137](1) 5-Hydroxy-2-(4′-benzyloxyphenyl)-4H-1-{2,2-diphenyl-[1,3]-dioxo[5,4-d]benzene Preparation of}pyran-4-one (7)

[0138] Take (200mg, 0.44mmol) 3 into 10mL of DMF, add (107mg, 0.78mmol, 1.75equiv) K 2 CO 3 After reacting at room temperature for 30 minutes, BnBr (0.08 mL, 0.66 mmol, 1.5 equiv) was added and reacted at room temperature for 6 hours. The reaction solution was diluted with 80mL water, extracted with 20mL×4 ethyl acetate, washed three times with water, anhydrous Na 2 SO 4 dry. Filtrate, recover the solvent, separate and purify by silica gel column chromatography, eluent petroleum ether: ethyl acetate (8:1). 197 mg of yellow solid 7 was obtained, with a yield of 83%. 1 H NMR (300MHz, DMSO-d 6 )δ: 13.10 (s, 1H, 5-OH); 10.40 (s, 1H, 4′-OH); 8.03-8.05 (d, 2H, J=8.7Hz, 2′, 6′-H); 7.55- 7.61;7.46-7.48and 7.32-7.43(each m,15H,-Ph);7.21-7.24(d,2H,J=8.7Hz,3′,5′-H);7.08(s,1H,8...

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Abstract

The invention relates to the field of pharmaceutical chemistry study, in particular to a novel scutellarin aglycone methylate product based on in-vivo metabolic mechanism as well as a preparation method of the novel scutellarin aglycone methylate product and an application of the novel scutellarin aglycone methylate product to thrombus prevention and treatment medicine. Pharmacological experiment results show that the scutellarin aglycone methylate product provided by the invention has pharmacological effects of better solubility, antioxidation, cell damage inhabitation and the like, and can be developed into novel medicine for preventing and treating thrombotic diseases.

Description

technical field [0001] The invention relates to the field of medicinal chemistry research, in particular to a new type of scutellarin aglycone methylation product based on in vivo metabolism mechanism, its preparation method and its application in anti-thrombotic drugs. Background technique [0002] Scutellaria scutellarin is a flavonoid compound in breviscapus breviscapus, a plant of the family Asteraceae. Erigeron breviscapus is also known as scutellaria breviscapus, also known as scutellaria breviscapus, soil asarum, chrysanthemum, asarum, oriental chrysanthemum, etc., scutellaria breviscapus Cold in nature, slightly bitter, sweet and warm, has the effects of dispelling cold and relieving the exterior, expelling wind and dampness, promoting blood circulation and removing blood stasis, dredging meridian and activating collaterals, reducing inflammation and relieving pain. Breviscapine is a flavonoid active ingredient extracted from the natural plant breviscapine, including...

Claims

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Application Information

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IPC IPC(8): C07D311/30A61K31/352A61P7/02A61P9/10
CPCY02P20/55
Inventor 李念光唐于平段金廒
Owner NANJING UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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