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3-substituted oxygen group-3',4'-dimethoxy flavonoid compound with blood fat reducing function

A technology of dimethoxyflavone and compound, applied in the field of medicine

Active Publication Date: 2008-08-20
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When R is the compound of acetyl group: 3-acetoxy-3', 4'-dimethoxyflavone and R is the compound of methyl: 3,3', 4'-trimethoxyflavone has no decrease Reports on the effects of blood lipids

Method used

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  • 3-substituted oxygen group-3',4'-dimethoxy flavonoid compound with blood fat reducing function
  • 3-substituted oxygen group-3',4'-dimethoxy flavonoid compound with blood fat reducing function
  • 3-substituted oxygen group-3',4'-dimethoxy flavonoid compound with blood fat reducing function

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1 Preparation of 3-acetoxy-3', 4'-dimethoxyflavone (compound 2) (R=acetyl in the general formula I)

[0043] Take 100mg of compound 1, 10ml of acetic anhydride, 1 drop of concentrated sulfuric acid, and stir at room temperature for 3h. Then, 100 ml of water was added to the reaction liquid, and stirring was continued overnight. After filtration, the solid was dried and recrystallized with isopropanol to obtain compound 2 as a slightly yellow solid with a melting point of 106-108° C. and a yield of 70%.

[0044] 1 HNMR (CDCl 3 )δ, ppm: 2.37 (3H, s, -CH 3 ), 3.95, 3.97 (6H, d, -OCH 3), 6.98~7.01(1H, d, 2'-H), 7.41~7.43(2H, m, 5', 6'-H), 7.52~7.58(2H, m, 6, 8-H), 7.69~ 7.74(1H, m, 7-H), 8.25~8.26(1H, m, 5-H).

[0045] MS(ESI)M + =341

Embodiment 2

[0046] Example 2 Preparation of 3-propionyloxy-3', 4'-dimethoxyflavone (compound 3) (R = propionyl in general formula I)

[0047] Take 100 mg of compound 1 and 10 ml of propionic anhydride, and follow the method of Example 1 to obtain compound 3 as a light yellow solid with a melting point of 148-150° C. and a yield of 60%.

[0048] 1 HNMR (CDCl 3 )δ, ppm: 1.26 ~ 1.30 (3H, t, -CH 3 ), 2.68~2.70 (2H, m, -CH 2 -), 3.96, 3.977 (6H, d, -OCH 3 ), 6.98~7.01(1H, d, 2'-H), 7.42~7.47(2H, m, 5', 6'-H), 7.52~7.58(2H, m, 6, 8-H), 7.69~ 7.72(1H, m, 7-H), 8.25~8.27(1H, m, 5-H).

[0049] MS(ESI)M + =355

Embodiment 3

[0050] Example 3 Preparation of 3-butyryloxy-3',4'-dimethoxyflavone (compound 4) (R=butyryl in general formula I)

[0051] Take 100mg of compound 1, 65mg of NaOH, 5ml of water, and 5ml of THF. Add 5ml of THF solution containing 1ml of butyryl chloride at a temperature below 5°C. After dropping, continue to react at this temperature for 1h, then pour the reaction solution into 50ml of water, and filter the precipitated solid. Recrystallized from isopropanol to obtain compound 4 as a pale yellow solid with a melting point of 113-116°C.

[0052] 1 HNMR (CDCl 3 )δ, ppm: 1.01 ~ 1.06 (3H, t, -CH 3 ), 1.77~1.84 (2H, m, -CH2-), 2.60~2.65 (2H, t, -OCH 2 -), 3.96~3.99 (6H, d, -OCH 3 )6.98~7.01(1H, d, 2'-H), 7.41~7.44(2H, m, 5', 6'-H), 7.52~7.58(2H, m, 6, 8-H), 7.69~7.75 (1H, m, 7-H), 8.25~8.28 (1H, m, 5-H).

[0053] MS(ESI)M + =369

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Abstract

The invention relates to a flavone compound using 3- to replace oxygen radical -3 and 4- dimethoxy and having the function of reducing blood fat, belonging to the technical field of medicine. The chemical construction is like the general formula I; wherein, R stands for H, alhyl radical and acyl radical. Shown by animal experiments, the flavone compound has the function of reducing the triglyceride of serum, the cholesterol and the cholesterol level of LDL and can thus prepare into the medicine or health-caring food for treating or preventing cardiovascular diseases such as hyperlipemia, coronary heart disease and atherosclerosis.

Description

Technical field: [0001] The invention relates to the technical field of medicine, and relates to a class of 3-substituted oxy-3',4'-dimethoxyflavonoids with blood lipid-lowering effect and a preparation method and application thereof. Background technique: [0002] Hyperlipidemia is a common cardiovascular disease, mainly caused by disorders of blood lipid metabolism, clinically divided into primary hyperlipidemia and secondary hyperlipidemia, often manifested as hypercholesterolemia (increased TC), hypertriglyceridemia (increased TG), or both. It is closely related to the occurrence and development of arteriosclerosis and cardiovascular diseases. Vascular diseases caused by abnormal blood lipids, such as high low-density lipoprotein cholesterol, high triglyceride, especially low high-density lipoprotein cholesterol, such as peripheral vascular disease, coronary heart disease, stroke disease, vascular restenosis, etc. Vascular disease has become a risk factor that seriousl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/352A61P3/06A61P9/10A61P1/16
Inventor 金永生姜远英吴秋业刘广泉戴阳刘文宝
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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