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Flavone glycoside derivatives, and preparation method and application thereof

A technology of flavonoid glycosides and flavone glycosides, which is applied in the field of pharmacy and can solve problems such as organ damage and toxic side effects

Inactive Publication Date: 2016-04-13
GUIZHOU BAILING GRP PARMACEUTIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among the above hypoglycemic drugs, there are drugs with fast drug effect and good curative effect, but they all have certain toxic and side effects, and damage the liver, kidney, gastrointestinal and other organs. Some diabetic patients show obvious drug resistance to insulin, and the existing There is no drug in the medicine that can eradicate diabetes, and patients need to take medicine for a long time. Therefore, it is an urgent need for the society to find new safe and effective diabetes treatment drugs

Method used

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  • Flavone glycoside derivatives, and preparation method and application thereof
  • Flavone glycoside derivatives, and preparation method and application thereof
  • Flavone glycoside derivatives, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1 Synthesis of aglycone intermediate 7,4'-di-hydroxyl-3,5,3'-tri-methoxy-flavone (M-04)

[0031]

[0032] Reagents and conditions: (i) BnBr, K 2 CO 3 , DMF, room temperature; (ii) concentrated hydrochloric acid, ethanol, 70 ° C, 3h. (iii) CH 3 I, K 2 CO 3 , DMF, room temperature, 8h; (iv) H 2 , 10% Pd / C, THF, room temperature 15h.

[0033] Preparation steps: (i) Weigh the obtained anhydrous rutin (50g, 80mmol) into a 1000mL reaction bottle, add 600mL anhydrous DMF, stir and dissolve, then add anhydrous K 2 CO 3 (23.8g, 168mmol, 2.1eq) and benzyl bromide (19.4mL, 160mmol, 2eq). React overnight at room temperature, pour the resulting reaction solution into an ice-water bath, add HCl to adjust the pH to 6, a large amount of precipitate precipitates, filter, and wash the filter cake with water to obtain M-01; (ii) take the crude M-01 obtained in the previous step and use Heat and dissolve 600mL of ethanol in water, then add 200mL of concentrated hydrochl...

Embodiment 2

[0034] Example 2 Synthesis of aglycon intermediate 7,4'-di-hydroxy-3,5,3'-tri-ethoxy-flavone (M-06)

[0035]

[0036] Reagents and conditions: (i) CH 3 CH 2 I, K 2 CO 3 , DMF, room temperature, 8h; (ii) H 2 , 10% Pd / C, THF, room temperature 15h.

[0037] Preparation steps: (i) Weigh the aforementioned synthetic intermediate M-02 (10g, 20.7mmol) into a 500mL reaction bottle, add 150mL of anhydrous DMF to dissolve completely, and then add anhydrous K 2 CO 3 (25.8g, 186mmol, 9eq) and CH 3 CH 2 I (6.6mL, 82.8mmol, 4eq), after reacting at 40°C for 8h, the reaction solution was dispersed with ethyl acetate and water, extracted, and the obtained organic layer was washed successively with dilute hydrochloric acid (0.1M), water and saturated brine. Dry over magnesium sulfate and concentrate, and the residue is purified by silica gel column chromatography to obtain the pure product M-05 in the form of light yellow powder with a yield of 90%. (ii) Weigh 10g (17.7mmol) of M-05...

Embodiment 3

[0038] Example 3 Synthesis of aglycone intermediate 3,5-di-hydroxyl-7,3',4'-tri-benzyloxy-flavone (M-08)

[0039]

[0040] Reagents and conditions: (i) BnBr, K 2 CO 3 , DMF, room temperature; (ii) ethanol, concentrated hydrochloric acid, 70 ° C, 3h.

[0041] Preparation steps: (i) Weigh the obtained anhydrous rutin (50g, 0.08mol) into a 1000mL reaction bottle, add 600mL anhydrous DMF, stir to dissolve, then add anhydrous K 2 CO 3 (56g, 0.41mol, 5eq) and benzyl bromide (36.9mL, 0.3mol, 3.8eq), react at room temperature for 2.5 days, after thin layer chromatography (TLC) detects that the reaction is complete, pour the reaction solution into an ice-water bath and wash with concentrated hydrochloric acid Adjust the pH to 6, precipitate a large amount of precipitate, filter, and the filter cake is the intermediate M-07 crude product; (ii) directly dissolve the M-07 crude product with absolute ethanol (600mL) and add concentrated hydrochloric acid (200mL) to react The liquid ...

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Abstract

The invention discloses flavone glycoside derivatives which are compounds with a general structural formula I shown in the description, and pharmaceutically acceptable salts or hydrates thereof, including racemates, optical isomers and epimers of the derivatives. The invention also discloses a preparation method of the flavone glycoside derivatives, and an application of the derivatives in preparing medicines used for treating diabetes. When the flavone glycoside derivatives provided by the invention are used in preparing medicines used for treating diabetes, the derivatives have good inhibition effects on alpha-glucosidase, such that the speed that starch breaks down into glucose is reduced, intestinal absorption of glucose is retarded, and the phenomenon of postprandial hyperglycemia is reduced. Therefore, the activity of the compounds in treating diabetes is improved, the toxicity is lower, and the physiochemical properties are more suitable for pharmaceutical preparations used for treating diabetes. The derivatives can be used for preparing diabetes-treating medicines with better efficacy and higher safety. The preparation method has the advantages of simple steps, easily available raw materials, high product yield, and high product purity. The flavone glycoside derivatives can be prepared into various pharmaceutical preparations used for treating diabetes.

Description

technical field [0001] The invention relates to a class of flavonoid glycoside derivatives, a preparation method and application thereof, and belongs to the field of pharmacy. Background technique [0002] Diabetes mellitus is a disorder of glucose metabolism caused by insufficient insulin secretion, low insulin action or insulin resistance (IR), resulting in elevated blood sugar and a disorder of sugar, fat and protein metabolism characterized by the coexistence of various complications. Type 1 diabetes is characterized by a lack of insulin secretion and requires daily insulin injections for treatment. Type 2 diabetes is characterized by the inability of the human body to utilize insulin effectively, requiring oral hypoglycemic drugs for intervention. Among diabetic patients, more than 90% have type 2 diabetes. At present, diabetes has become the third major disease that threatens human health after cardiovascular and cerebrovascular diseases and tumors worldwide. The inc...

Claims

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Application Information

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IPC IPC(8): C07H17/07C07H1/00A61K31/7048A61P3/10
CPCA61P3/10C07H1/00C07H17/07
Inventor 徐必学梁光义胡占兴夏文姜伟袁洁陈洪菊张丽梅蒋坤孙晓军李星安巧
Owner GUIZHOU BAILING GRP PARMACEUTIAL CO LTD
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