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O-glycoside nitrone compound and synthetic method thereof

A technology for glycoside nitrones and compounds is applied in the field of O-glycoside nitrones and their synthesis, which can solve the problems of limited wide application, poor absorption capacity of the body with toxic and side effects, etc., and achieves extended application range, cheap raw materials, and enhanced activity. Effect

Inactive Publication Date: 2010-09-08
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are quite a few drugs, which have their own toxic side effects or poor absorption capacity of the body, which limits their wide application

Method used

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  • O-glycoside nitrone compound and synthetic method thereof
  • O-glycoside nitrone compound and synthetic method thereof
  • O-glycoside nitrone compound and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: Synthesis of C-[4-hydroxybenzaldehyde-2,3,4,6-tetraacetyl-O-β-(D)-glucoside]-N-phenylnitrone:

[0035] (1) Synthesis of 1,2,3,4,6-pentaacetyl-β-(D)-glucopyranose

[0036] Zinc chloride (3.7mmol) was added in batches to a round bottom flask containing glucose (14mmol) and acetic anhydride (123mmol), reacted at 100°C for 1 hour, cooled, the mixture was poured into ice water and stirred fully, white The precipitate is formed, filtered, washed with cold water, and recrystallized with ethanol to obtain white crystals. Yield: 52%. The reaction equation is as follows:

[0037]

[0038] (2) Synthesis of 2,3,4,6-tetraacetyl-β-(D)-bromoglucopyranose

[0039] Red phosphorus (29 mmol) was added to a 100 ml round bottom flask containing acetic acid (15 ml) and stirred vigorously for 5 minutes. Then liquid bromine (34mmol) was slowly added dropwise to the reaction flask, and the temperature was controlled between 15°C and 25°C. After the dropwise addition, continued stirring unt...

Embodiment 2

[0048] Example 2: Synthesis of C-[2-hydroxybenzaldehyde-2,3,4,6-tetraacetyl-O-β-(D)-glucoside]-N-phenylnitrone

[0049] (1) Synthesis of 1,2,3,4,6-pentaacetyl-β-(D)-glucopyranose

[0050] Same as Example 1 step (1).

[0051] (2) Synthesis of 2,3,4,6-tetraacetyl-β-(D)-pyran bromoglucose

[0052] Same as step (2) of Example 1.

[0053] (3) Synthesis of 2-hydroxybenzaldehyde-2,3,4,6-tetraacetyl-O-β-(D)-glucopyranoside

[0054] In a 100 ml three-necked flask containing tetrabutylammonium chloride (4.3 mmol), 15 ml of chloroform and water were added to dissolve them. Dissolve in KCO 3 O-Hydroxybenzaldehyde in aqueous solution (containing KCO 3 21.7mmol, water 10ml, o-hydroxybenzaldehyde 8.7mmol) and bromosugar solution in chloroform (6.08ml chloroform, 7.3mmol bromosugar prepared in step (2) above) were added dropwise to the reaction flask at the same time, and the temperature was controlled. At 58°C, TLC detected the reaction to completion (about 3-6h), then the reaction solution was coole...

Embodiment 3

[0060] Example 3, C-[4-hydroxy-3-methoxybenzaldehyde-2,3,4,6-tetraacetyl-O-β-(D)-glucoside]-N-phenylnitrone synthesis

[0061] (1) Synthesis of 1,2,3,4,6-pentaacetyl-β-(D)-glucopyranose

[0062] Same as Example 1 step (1).

[0063] (2) Synthesis of 2,3,4,6-tetraacetyl-β-(D)-pyran bromoglucose

[0064] Same as step (2) of Example 1.

[0065] (3) Synthesis of 4-hydroxy-3-methoxybenzaldehyde-2,3,4,6-tetraacetyl-O-β-(D)-glucopyranoside

[0066] In a 100 ml three-necked flask containing tetrabutylammonium chloride (4.3 mmol), 15 ml of chloroform and water were added to dissolve them. Dissolve in K 2 CO 3 Vanillin in aqueous solution (K 2 CO 3 21.7mmol, water 10ml, vanillin 8.7mmol) and bromosugar solution in chloroform (6.08ml chloroform, 7.3mmol for bromosugar prepared in step (2)) were added dropwise to the reaction flask at the same time, the temperature was controlled at 58℃ , TLC detects that the reaction is complete (about 3-6h), then the reaction solution is cooled to room temperatu...

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Abstract

The invention provides an O-glycoside nitrone compound which is a novel nitrone glycoside and a synthetic method thereof, belonging to the field of chemical synthesis. The compound is synthesized by the following steps of: firstly catalyzing sugar and acetic anhydride with acid to produce totally acetylated sugar; then reacting the totally acetylated sugar with red phosphorus and liquid bromine under an acidic condition to generate brominated sugar; then reacting the brominated sugar with hydroxyl-contained aromatic aldehyde under the action of a phase transfer catalyst to produce O-benzaldehyde glycoside; and finally reacting the O-benzaldehyde glycoside with N-substituted hydroxylamine to obtain a target product. The O-glycoside nitrone compound has single beta-form configuration and simultaneously has the advantages of natural chirality, structural diversity and the like. The synthetic method has the advantages of low price and easy obtained raw materials, environmental protection, reproducibility and the like and creates a good condition for industrialization.

Description

Technical field [0001] The invention belongs to the technical field of chemical synthesis, and relates to a nitroglycoside compound and a synthesis method thereof, in particular to an O-glycoside nitrone compound and a synthesis method thereof. Background technique [0002] Compounds and sugars form glycosides, that is, after glycosylation modification, their physical and chemical properties will change accordingly. Glycoside compounds have the following biological properties: (1) As a pharmacokinetic group, it affects the absorption, distribution, metabolism, and excretion of drugs. It has the properties of improving water solubility, enhancing stability and changing pharmacokinetics. (2) Since sugars have many biological activities, they are used as pharmacophores to participate in the design of drugs. (3) Operate as targeted drugs and drugs. There are quite a lot of drugs that have toxic side effects or poor absorption capacity of the body, which limits their wide applicatio...

Claims

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Application Information

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IPC IPC(8): C07H15/203C07H1/00
Inventor 傅颖张怀远刘彦华胡雪梅王明珠李姣
Owner NORTHWEST NORMAL UNIVERSITY
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