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Myricetin derivative and application thereof for preparing medicine capable of reducing blood sugar and reducing blood fat

A technology of derivatives and myricetin, which is applied in the direction of sugar derivatives, drug combinations, pharmaceutical formulations, etc., can solve the problems of poor water solubility, stability and bioavailability, which affect the development and application of myricetin, and achieve a large market value, The effect of high yield and high product purity

Inactive Publication Date: 2019-12-03
MARINE BIOMEDICAL RES INST OF QINGDAO CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although myricetin has a variety of pharmacological blood activities, its water solubility, stability and bioavailability are poor, which affects the development and application of myricetin.

Method used

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  • Myricetin derivative and application thereof for preparing medicine capable of reducing blood sugar and reducing blood fat
  • Myricetin derivative and application thereof for preparing medicine capable of reducing blood sugar and reducing blood fat
  • Myricetin derivative and application thereof for preparing medicine capable of reducing blood sugar and reducing blood fat

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] The synthetic route of myricetin derivative M2 is as follows:

[0052]

[0053] Myricetin (100g, 0.22mol) was dissolved in N,N-dimethylformamide (1L), then potassium carbonate (300g, 2.16mol) was added, and benzyl bromide (370g, 12.16 mol), after addition, heated to 80°C for 60 hours. After the reaction was completed, cool to room temperature, add 3L of water to the reaction system, precipitate the solid under stirring, filter, add the solid to 3L of water / dichloromethane mixed solution with a volume ratio of 1:1, and adjust the pH value with 2N hydrochloric acid to Acidity, the organic phase was separated, and the aqueous phase was extracted 3 times with dichloromethane. The organic phases were combined, dried and concentrated to obtain 200 g of M2, which was directly used in the next step without purification.

Embodiment 2

[0055] The synthetic route of myricetin derivative M3 is as follows:

[0056]

[0057] Dissolve M2 (200g) obtained in Example 1 into tetrahydrofuran (1L), then add 3N hydrochloric acid (1L), and heat to reflux for 12 hours. L of ethanol / dichloromethane mixed solution with a volume ratio of 1:1 was heated to reflux for beating for 4 hours, cooled to room temperature, and filtered to obtain 67g of yellow solid M3 with a yield of 45%.

[0058] 1 H NMR (500MHz, DMSO-d6)δ=12.35(s,1H),9.85(s,1H),7.67(s,2H),7.50(t,J=6.7Hz,6H),7.39(m,12H) ,7.29(d,J=1.5Hz,2H),6.90(d,J=2.2Hz,1H),6.48(d,J=2.2Hz,1H),5.26(s,2H),5.20(s,4H) , 5.05 (s, 2H) ppm. ESI-MS: (m / z, %) = 677 [M-H]-.

Embodiment 3

[0060] The synthetic route of myricetin derivative M5-X is as follows:

[0061]

[0062] The benzyl-protected myricetin derivative M3 (30g, 44.2mmol) was added into dichloromethane (500mL), and then various acetyl-protected bromoglycosides (53mmol), tetrabutylammonium bromide (17g, 53mmol) and potassium carbonate (23g, 165.8mmol) in aqueous solution (200mL), heated to 45°C and stirred for 3 hours, then added water to separate the layers, the organic phase was washed with water and saturated brine successively, dried, and column chromatography gave yellow solid M5- X.

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PUM

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Abstract

The invention provides a myricetin derivative disclosed in a formula (I), a pharmaceutically acceptable salt of the myricetin derivative, and a preparation method for the myricetin derivative, and also provides the purpose of the myricetin derivative for preparing a medicine capable of reducing blood sugar and / or reducing blood fat. The myricetin derivative disclosed by the invention can obviously inhibit the activity of [alpha]-glucosidase, the effect of the myricetin derivative is obviously superior to the effect of acarbose which is widely clinically applied, and the myricetin derivative has a good application prospect.

Description

technical field [0001] The invention belongs to the field of medicine, and relates to a myricetin derivative and a preparation method thereof, and its application in treating colitis, preventing and treating cancer transformation of colitis and treating colon cancer. The invention belongs to the field of medicaments, and relates to a myricetin derivative, a preparation method thereof, and an application thereof in the preparation of medicines for treating blood sugar-lowering and blood-lipid-lowering diseases. Background technique [0002] Myricetin, also known as myricetin, myricetin, belongs to flavonoids, chemical name 3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzofuran- 4-ketone is the main chemical component of the leaves, bark and root of Myricaceae, and it also exists in onions, berries and other plants. Studies have shown that myricetin has a variety of pharmacological activities: (1) anti-platelet activating factor (PAF), has various cardiovascular pharmaco...

Claims

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Application Information

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IPC IPC(8): C07H17/07A61K31/7048A61P3/06A61P3/10
CPCA61P3/06A61P3/10C07B2200/07C07H17/07
Inventor 李文保杨冲李峰张良管华诗
Owner MARINE BIOMEDICAL RES INST OF QINGDAO CO LTD
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