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Application of quercetin-O-glucoside derivative to treatment of lipid metabolism disorders

A compound and solvate technology, applied in the field of medicine, can solve the problems of complex pathogenesis and difficult treatment

Active Publication Date: 2014-07-30
NANJING RUIJING PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The pathogenesis of lipid metabolism disorders is complicated, and it is difficult to treat them at present

Method used

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  • Application of quercetin-O-glucoside derivative to treatment of lipid metabolism disorders
  • Application of quercetin-O-glucoside derivative to treatment of lipid metabolism disorders
  • Application of quercetin-O-glucoside derivative to treatment of lipid metabolism disorders

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Synthesis of Quercetin-3-O-β-D-glucoside (Compound 2)

[0067] Put 50 g (150 mmol) of quercetin, 50 mL (256 mmol) of diphenylmethylene chloride, and 100 mL of diethylene glycol dimethyl ether into a 200 mL single-necked flask, and heat to reflux for 10 minutes. The solvent was distilled off under reduced pressure to obtain a yellow syrup, which was purified by silica gel column chromatography to obtain a light yellow solid (35.67g, 46.32%). 23.3g (50mmol) of the compound obtained in the previous step was followed by 13.8g (100mmol) of potassium carbonate Dissolve in tetrahydrofuran solution (100mL), slowly add 19.85g (50mmol) of acetyl bromide-α-D-glucose to it under stirring, control the temperature of the reaction solution at 0-5°C, and continue to stir and react at this temperature for 8 Hour. The reaction solution was diluted with 40 mL of dichloromethane, filtered to remove the remaining potassium carbonate, the filtrate was distilled, the organic layer was dried ...

Embodiment 2

[0070] Synthesis of 3',4'-Dihydroxymethylquercetin-3-O-β-D-glucoside (Compound 3)

[0071] The first two steps are the same as in Example 1. The obtained light yellow syrup (6.18g, 10mmol), bromomethanol (1.09g, 10mmol), and potassium carbonate (1.38g, 10mmol) are successively dissolved in 50ml of tetrahydrofuran solution, and the heating bar Added and refluxed for 7 hours, and then purified by silica gel column chromatography to obtain a light yellow solid, to which was added 15 mL of sodium methoxide solution, reacted at room temperature for 3 hours, and separated by polyamide column chromatography (chloroform:methanol=7:1). A light yellow solid (3.23 g, 67.2%) was obtained, mp 231-235°C.

[0072] 1 H-NMR (400MHz, DMSO-d 6 ): δ3.34–3.67(m,6H),4.27-4.31(m,4H),5.25(d,J=7.6Hz,1H),6.16(d,J=1.6Hz,1H),6.38(d, J=2.0Hz, 1H), 6.54(s, 2H), 6.56(d, J=8.4Hz, 1H), 7.46(dd, J=8.4, 2.0Hz, 1H), 7.75(d, J=2.0Hz, 1H).MS(m / z):525.3[M+H] + .

Embodiment 3

[0074] Synthesis of Quercetin-3-O-β-D-glucuronide (Compound 4)

[0075] The preparation process is the same as in Example 1, except that the acetyl bromide-α-D-glucose used in the second step is replaced by acetyl bromide-α-D-glucuronide methyl ester, the reaction yield is 46.7%, mp 245~248°C.

[0076] 1 H-NMR (400MHz, DMSO-d 6 ): δ3.30–3.60(m,6H),5.15(d,J=7.6Hz,1H),6.10(d,J=1.6Hz,1H),6.30(d,J=2.0Hz,1H),6.71 (d,J=8.4Hz,1H),7.49(dd,J=8.4,2.0Hz,1H),8.27(d,J=2.4Hz,1H).MS(m / z):479.1[M+H] + .

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Abstract

The invention relates to the field of drug synthesis and pharmacology and in particular relates to a preparation method of a quercetin-O-glucoside derivative and an application of the quercetin-O-glucoside derivative to treatment of lipid metabolism disorders. The derivative is a compound in a formula I in the specification and comprises salt, optical isomers and racemes of the compound in the formula I. The invention aims to design and synthesize the quercetin-O-glucoside derivative. Through in vitro and in vivo pharmacological activity study, the quercetin-O-glucoside derivative can play a role in reducing the lipid in the in vivo and in vitro experiments. Besides, the invention also provides a drug composition for treating lipid metabolism disorders.

Description

technical field [0001] The invention relates to the field of medicine, in particular to the application of a class of quercetin-O-glycoside derivatives in the treatment of disorders of lipid metabolism. Background technique [0002] With the development of the economy and the change of the national lifestyle, the incidence of a series of lipid metabolism disorders is increasing day by day. Lipid metabolism disorders refer to energy metabolism-related diseases mainly characterized by abnormal lipid metabolism in the body, including fatty liver, obesity, atherosclerosis, and hyperlipoproteinemia. Clinically, the main feature of lipid metabolism disorder is the abnormality of lipid (lipid) and its metabolites in the blood and other tissues and organs, which can show the accumulation of triglyceride and cholesterol, liver lobular inflammation and The content of alanine transaminase (ALT) increased and the secretion of adipocytokines changed. The pathogenesis of lipid metabolis...

Claims

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Application Information

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IPC IPC(8): C07H17/07C07H1/00A61K31/7048A61P3/06A61P1/16A61P9/10
CPCA61P1/16A61P3/06A61P9/10C07H17/07
Inventor 尚靖李妤金雨吕金鹏王路路张志超
Owner NANJING RUIJING PHARMA TECH CO LTD
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