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1-deoxidization nojiri toxin derivant, production method and uses thereof

A technology for deoxidizing Nojiri and derivatives, applied in organic chemistry and other directions, can solve problems such as high cost, difficulty in expanding production, and difficulty in chemical synthesis.

Inactive Publication Date: 2008-06-11
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] As an important drug and drug intermediate, 1-deoxynojiri toxin has always been mostly extracted from plants, and it is difficult to expand production. However, due to the involvement of multi-chirality and multi-hydroxyl groups, chemical synthesis is very difficult and costly. Therefore, there is an urgent need to explore a mild, high-yield, and low-cost method to prepare 1-deoxynojiri toxin, which will lay a solid foundation for the development of drug intermediates for diabetes, diabetic complications, viral infections, and obesity. , which is of great significance to the research and development of 1-deoxynojiri toxin

Method used

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  • 1-deoxidization nojiri toxin derivant, production method and uses thereof
  • 1-deoxidization nojiri toxin derivant, production method and uses thereof
  • 1-deoxidization nojiri toxin derivant, production method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 Preparation of 1,2,5,6-position propylidene protected D-glucoside

[0027] Dissolve 15g D-glucose in 300ml acetone, add ZnCl 2 8g, electromagnetically stirred at room temperature for 10h, neutralized with 50% NaOH to neutral after detection, filtered with suction, evaporated to dryness, crystallized with cyclohexane to obtain 13.4g of white double-protected needle crystals, melting point 110.2℃~111.0℃ , yield 89.3%. (Document: 111.5~112.7℃)

[0028] 1 H-NMR δ: 5.95 (1H, d, J=3.6HZ, 1-H); 4.54 (1H, d, J=3.6Hz, 2-H); 4.37~4.32 (2H, m, 3-H, 4 -H); 4.17 (1H, dd, J = 6.4Hz, 8.8Hz, 5-H); 4.08 (1H, dd, J = 2.4Hz, 7.2Hz, 6-H); 3.98 (1H, dd, J = 5.2Hz, 8.4Hz, 6-H); 1.50, 1.45, 1.37, 1.32 (each3H, s, 4CH 3 ).

[0029] Anal. Clcd for C 12 h 20 o 6 : C, 55.35; H, 7.74 Found: C, 55.37; H, 7.76.

Embodiment 2

[0030] Example 2 Preparation of 1,2-position propylidene protected D-glucoside

[0031] Dissolve 18g of 1,2,5,6-position propylidene-protected D-glucoside in 80ml of methanol, add 80ml of 0.8% sulfuric acid, stir electromagnetically at room temperature for 24h, then neutralize with barium carbonate, heat to a slight boil, and filter And the filtrate was evaporated to dryness, and recrystallized with methanol-ether to obtain white needle-like crystals. Yield: 98.2%, melting point: 160.0-161.5°C (literature value: 160.0-161.0°C)

[0032] 1 H-NMR δ: 5.98 (1H, d, J = 3.6HZ, 1-H); 4.55 (1H, d, J = 3.6Hz, 2-H); 4.37 (1H, d, J = 3.2Hz, 3- H); 4.14~4.18(1H, m, 4-H); 4.10(1H, dd, J=2.8Hz, 6.0Hz, 5-H); 3.93(1H, dd, J=3.2Hz, 11.2Hz, 6 -H); 3.78 (1H, dd, J = 6.0Hz, 11.6Hz, 6-H); 1.50, 1.33 (each 3H, s, CH 3 ).

[0033] Anal. Clcd for C 9 h 16 o 6 : C, 49.09; H, 7.32 Found: C, 49.05; H, 7.34.

Embodiment 3

[0034] Example 3 Preparation of dicarbonyl D-glucose shown in structural formula 2

[0035] 5.0 g of D-glucoside protected by 1,2-position propylidene and 30.0 g of dibutyltin oxide were dissolved in 200 ml of anhydrous toluene, protected by argon, and refluxed for 4 hours. Lower the temperature of the reaction system to 0-5°C, add bromine dropwise until the reddish-brown color does not fade, continue the reaction for 1 hour, add 50ml of water, extract bibutyltin oxide with toluene, neutralize the aqueous phase with sodium bicarbonate until neutral, freeze Dry, dissolve with ether, filter out inorganic salts, freeze and crystallize to obtain white crystals (98.2% yield, melting point 109.5°C-110.2°C (literature value: 108.0-110.0°C); 1H-NMR δ: 5.89 (1H, d, J = 3.6HZ, 1-H); 4.40 (1H, d, J = 3.6Hz, 2-H); 3.94 (1H, d, J = 2.8Hz, 4- H); 3.73 (1H, d, J = 12.4Hz, 6-H); 3.57 (1H, d, J = 12.4Hz, 6-H); 1.34, 1.22 (each 3H, s, CH 3 ): Anal.Clcd for C 9 h 14 o 6 : C, 49.54; H, 6.47 ...

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Abstract

The invention discloses a 1-deoxidized nojiri toxin derivative and a relative preparation method, which uses natural cheap D-glucose as material to synthesize dicarbonyl-D-glucose, and processes enamine double-reduction reaction on the dicarbonyl-D-glucose and amine, to obtain 1-deoxidized nojiri toxin derivative with high yield and spatial selectivity. The derivative can be used as intermediate and chiral auxiliary of organic synthesis or drug synthesis, to chirally synthesize organic or drug. The invention further discloses a full synthesis process of 1-deoxidized nojiri toxin derivative, with spatial control, simple operation, mild condition, high yield and industrialization suitability.

Description

technical field [0001] The invention belongs to the technical field of sugar chemistry and medicinal chemistry, and specifically relates to 1-deoxynojiri toxin derivatives and a preparation method thereof. Background technique [0002] 1-Deoxynojirimycin (DNJ) is a piperidine alkaloid, and its chemical name is 3,4,5-trihydroxy-2-hydroxymethyltetrahydropyridine, which is the abbreviation of 1-deoxynojirimycin (structural formula 1). In the 1970s, 1-deoxynojiritoxin was first extracted and isolated as a natural product from the root core trunk of mulberry tree, named "moranoline". At the same time, 1-deoxynojiritoxin was extracted from the fermentation broth of Streptomyces, and it also exists in plants such as commelianceae, hyacinth, and sand ginseng. DNJ can efficiently inhibit α-glucosidase, thereby reducing the digestion of carbohydrates and the absorption of glucose to reduce the rise in blood sugar after eating. Therefore, DNJ can be used to treat diabetes, diabetic co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/40
Inventor 刘宏民张红雨赵玉芬
Owner ZHENGZHOU UNIV
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