1-deoxynojirimycin-hydroxychalcone hybrid derivative and its preparation method and application

A technology of deoxynojirimycin and hydroxychalcone, which is applied in the fields of medicine and food, can solve problems such as general effect and hinder disaccharide decomposition, and achieve the effect of reducing postprandial blood sugar and good application prospect.

Active Publication Date: 2020-06-30
JIANGXI AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

1-Deoxynojirimycin (1-DNJ) is an imino sugar that has been studied more at present. It has a chemical structure similar to glucose, and its affinity with α-glucosidase is greater than that of disaccharides, which can hinder the synthesis of disaccharides. Decomposed, it is a powerful competitive α-glucosidase inhibitor, but the substance is absorbed quickly in the body and is metabolized quickly, so the effect of inhibiting the rise of blood sugar after meals in the body is general

Method used

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  • 1-deoxynojirimycin-hydroxychalcone hybrid derivative and its preparation method and application
  • 1-deoxynojirimycin-hydroxychalcone hybrid derivative and its preparation method and application
  • 1-deoxynojirimycin-hydroxychalcone hybrid derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: Preparation of 1-deoxynojirimycin-hydroxychalcone hybrid derivative (DC-2)

[0040] (1) Preparation of intermediates of hydroxychalcones connected to the bridge:

[0041] Add 2g (13.5mmol) 2'-hydroxychalcone and 7.62g (40.5mmol) 1,2-dibromoethane raw materials into a 100mL round bottom flask, then add 3.7g (27mmol) potassium carbonate and 50mL acetone, Stir and react at 65°C until the end of the reaction; after the end of the reaction, pour the above reaction solution into water, extract with 20 mL of ethyl acetate, repeat the extraction 3 times, combine the organic phases; dry with anhydrous sodium sulfate , then desolvation and mixing of the sample, separation by silica gel column chromatography, the eluent is sherwood oil / ethyl acetate=20:1, and the middle of the hydroxychalcone that has inserted the connecting bridge of 2 carbon atoms is obtained. body; 1 HNMR (500MHz, DMSO) δ7.77(d, J=3.6Hz, 1H), 7.76(d, J=2.2Hz, 1H), 7.61(d, J=3.7Hz, 2H), 7.58(dd, J= ...

Embodiment 2

[0044] Example 2: Preparation of 1-deoxynojirimycin-hydroxychalcone hybrid derivative (DC-5)

[0045] (1) Preparation of intermediates of hydroxychalcones connected to the bridge:

[0046] Add 2g (13.5mmol) 2'-hydroxychalcone and 9.31g (40.5mmol) 1,5-dibromopentane raw materials into a 100mL round bottom flask, then add 3.7g (27mmol) potassium carbonate and 50mL acetone, Stir and react at 65°C until the end of the reaction; after the end of the reaction, pour the above reaction solution into water, extract with 20 mL of ethyl acetate, repeat the extraction 3 times, combine the organic phases; dry with anhydrous sodium sulfate , and then precipitate and mix the sample, adopt silica gel column chromatography to separate, the eluent is sherwood oil / ethyl acetate=20:1, and the intermediate of the hydroxychalcone that has inserted the connecting bridge of 5 carbon atoms is obtained body. 1 HNMR (500MHz, DMSO) δ7.78–7.63(m,2H), 7.52(dd,J=14.1,6.3Hz,4H),7.47–7.39(m,3H),7.16(d,J=8.5...

Embodiment 3

[0049] Example 3: Preparation of 1-deoxynojirimycin-hydroxychalcone hybrid derivative (DC-3)

[0050] (1) Preparation of intermediates of hydroxychalcones connected to the bridge:

[0051] Add 2g (13.5mmol) 2'-hydroxychalcone and 8.18g (40.5mmol) 1,3-dibromopropane raw materials into a 100mL round bottom flask, then add 3.7g (27mmol) potassium carbonate and 50mL acetone, Stir and react at 65°C until the end of the reaction; after the end of the reaction, pour the above reaction solution into water, extract with 20 mL of ethyl acetate, repeat the extraction 3 times, and combine the organic phases; dry with anhydrous sodium sulfate, Then desolventize and mix the sample, and use silica gel column chromatography to separate, the eluent is sherwood oil / ethyl acetate=20:1, and the intermediate of hydroxychalcone with a connecting bridge of 3 carbon atoms is obtained ; 1 HNMR(500MHz,DMSO)δ7.74(d,J=3.7Hz,1H),7.73–7.72(m,1H),7.56–7.51(m,3H),7.46(s,1H),7.45–7.42(m ,3H),7.20(d,J=8.2Hz...

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Abstract

The invention relates to the fields of medicine and food, in particular to 1-deoxynojirimycin-hydroxychalcone hybrid derivatives and their preparation methods and applications. 1-deoxynojirimycin-hydroxychalcone hybrid derivatives have a structure shown in formula (I), and it has been proved by in vitro tests that this type of compound is a potent inhibitor of α-glucosidase. The inhibitory activity is significantly higher than that of acarbose, the most commonly used postprandial blood glucose control agent at present. Among them, the activities of the two compounds DC‑5 and DC‑2 are also significantly higher than 1‑deoxynojirimycin. Since these compounds can strongly inhibit the activity of sugar-digesting enzymes such as α-glucosidase, and can effectively reduce postprandial blood sugar, they have very good application prospects in hypoglycemic drugs and auxiliary hypoglycemic foods.

Description

technical field [0001] The invention relates to the fields of medicine and food, in particular to a 1-deoxynojirimycin-hydroxychalcone hybrid derivative and a preparation method and application thereof. Background technique [0002] According to the statistics of the International Diabetes Federation (IDF), in 2013 there were about 382 million diabetic patients in the world, and 316 million people with impaired glucose tolerance, which cost 548 billion U.S. dollars in medical expenses each year, accounting for 11% of the total medical expenses; about 5,000 in my country million diabetics, ranking second in the world; in recent years, due to changes in eating habits, lifestyles and the environment, hyperglycemia and diabetes patients continue to increase, showing an accelerated upward trend. Hyperglycemia, diabetes and their complications have seriously damaged people's health, greatly reduced their quality of life, and at the same time caused a heavy economic burden to famili...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/46A61K31/445A61P3/10A23L7/104A23L5/10A23L33/00
CPCA23L5/13A23L7/104A23L33/00A23V2002/00A61P3/10C07D211/46A23V2200/328
Inventor 尹忠平彭大勇上官新晨陈继光吴少福林萍曾凡新
Owner JIANGXI AGRICULTURAL UNIVERSITY
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