Scutellarein derivative as well as preparation method and application thereof

A technology of scutellarin aglycone and scutellarin aglycon, which is applied in the field of medicinal chemistry research, can solve the problems of low adverse reactions and high bioavailability, and achieve the effects of low adverse reactions, high bioavailability, and improved bioavailability

Inactive Publication Date: 2010-11-24
NANJING UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] 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 as a raw material through alkylation, glycoside hydrolysis, selective methyl etherification, hydrogenation debenzylation, and 6-position alkylation. A series of scutellarin aglycon-6-position derivatives with medicinal val...

Method used

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  • Scutellarein derivative as well as preparation method and application thereof
  • Scutellarein derivative as well as preparation method and application thereof
  • Scutellarein derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1 4', the preparation of 6-dibenzyloxy-5-hydroxyl-7-glucuronic acid oxyflavone (2)

[0044] Add scutellarin 2.4g, DMF, K 2 CO 3 (2.5equiv), under the protection of inert gas nitrogen, add benzyl bromide (2.3equiv), react at 25°C for 8 hours, after the reaction, add ice water, control PH≤6, precipitate solid, suction filter, dry to obtain yellow solid 2.7 grams. Yield 81%.

[0045] The obtained compound spectral data is:

[0046] MS (TOF, m / z): 627.01 [M-H] - .

[0047] 1 HNMR (DMSO-d 6 , 300MHz): 12.97 (5-OH), 7.91 (2H, d, j=8.58, 2', 6'-ArH), 6.92 (2H, d, j=8.58, 3', 5'-ArH), 6.74 (1H, s, 3-H), 6.57 (1H, s, 8-H), 7.20 (10H, Ar-H), 5.22 (2H, s, H-CHAr), 5.16 (2H, s, H-CHAr ), 5.51 (1H, d, J=12, 1”-H).

Embodiment 2

[0048] Example 2 4', 5, the preparation of 7-trihydroxy-6-benzyloxyflavone (3)

[0049] Take 23.2 g of the compound prepared in Example 1, add it to 1 mol / L sulfuric acid ethanol solution, and react at 80°C for 12 hours under the protection of an inert gas. After the reaction, add ice water, control the pH at 5-6, and precipitate yellow The solid was filtered with suction, and the obtained crude product was purified by column chromatography to obtain 0.9 g of a yellow solid (eluent: dichloromethane: methanol). Yield 48%.

[0050] The obtained compound spectral data is:

[0051] MS (TOF, m / z): 375.01 [M-H] - .

[0052] 1 HNMR (DMSO-d 6 , 300MHz): 12.97 (5-OH), 10.44 (1H, s, 7-OH), 10.30 (1H, s, 4'-OH), 7.91 (2H, d, j=8.58, 2', 6'- ArH), 6.92 (2H, d, j=8.58, 3', 5'-ArH), 6.74 (1H, s, 3-H), 6.57 (1H, s, 8-H), 7.20 (5H, Ar- H), 5.18 (2H, s, 1”-H).

Embodiment 3

[0053] Example 3 4', the preparation of 7-dimethoxymethylene oxygen-5-hydroxyl-6-benzyloxyflavone (4)

[0054] 1.65g of K 2 CO 3 , 1.9 g of intermediate 3 were put into 30 ml of acetone in turn, stirred at room temperature for 30 minutes, then added MOMCl (1.5 equiv), heated to room temperature at 70° C. and stirred for 12 hours. After the reaction, add an appropriate amount of ice water to control the pH to 4-7, filter with suction, and wash the filter cake with a small amount of ice water. The obtained crude product was recrystallized to obtain 1.7 g of a yellow solid (solvent: ether / ethanol). Yield: 72.6%

[0055] The obtained compound spectral data is:

[0056] MS (TOF, m / z): 463.15 [M-H] - .

[0057] 1 HNMR (DMSO-d 6 , 300MHz): 12.97 (5-OH), 7.91 (2H, d, j=8.58, 2', 6'-ArH), 6.92 (2H, d, j=8.58, 3', 5'-ArH), 6.74 (1H, s, 3-H), 6.57 (1H, s, 8-H), 7.20 (5H, m, Ar-H), 5.22 (2H, s, 1”-H), 5.16 (2H, s, -OCH 2 O-), 5.23 (2H, s, -OCH 2 O-), 3.21 (3H, s, -OCH 3 ), 3....

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Abstract

The invention relates to the research field of medicinal chemistry, in particular to a novel scutellarein-6-site derivative (I), as well as a preparation method and an application thereof to medicines for preventing and treating thrombus. Pharmacological test results show that compared with scutellarin and scutellarein, the compound has better function of inhibiting platelet aggregation. The scutellarein-6-site derivative (I) provided by the invention can be used for treating a series of diseases caused by the thrombus, such as myocardial infarction, ischemia injury and so on.

Description

technical field [0001] The invention relates to the field of medicinal chemistry research, in particular to a novel scutellarin aglycon-6-position derivative (I), its preparation method and its application in antithrombotic drugs. Background technique [0002] Scutellarin aglycon is a flavonoid compound in breviscapus breviscapus, a plant of the family Asteraceae. Erigeron breviscapus is cold in nature, slightly bitter, sweet and warm, and 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 a mixture of scutellarin and scutellarin, mainly scutellarin (the content is more than 95%) (Chen Yiyue, Wang Shengtao, Zeng Wenshan, Zhu Yinghong, Fu Yongmei, Jiang Tao. Relaxation effect of breviscapine o...

Claims

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Application Information

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IPC IPC(8): C07D311/30C07D405/12A61K31/352A61K31/4025A61K31/5377A61K31/453A61P9/10A61P7/02
Inventor 唐于平李念光段金廒
Owner NANJING UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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