Sialic acid-carboxylic acid compound conjugate and preparation method thereof

A compound and carboxylic acid technology, applied in the field of medicinal chemistry, can solve the problems of uncontrollable product stereoselectivity, cumbersome operation, and low synthesis efficiency, and achieve the effects of high synthesis efficiency, simple operation, and reduced irritation

Active Publication Date: 2020-06-16
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this synthesis method has the problems of low synthesis efficiency, cumbersome operation, and uncontrollable stereoselectivity of the product.

Method used

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  • Sialic acid-carboxylic acid compound conjugate and preparation method thereof
  • Sialic acid-carboxylic acid compound conjugate and preparation method thereof
  • Sialic acid-carboxylic acid compound conjugate and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] A kind of preparation method of sialic acid-acetic acid conjugate, comprises the steps:

[0036] (1) Weigh 134mg (0.2mmol) of fully acetyl-protected sialyl glucosinolate donor 1 and 170mg of newly activated Add MS to the reaction flask, add 4 mL redistilled dichloromethane to dissolve, stir at 25°C under the protection of argon atmosphere, add 34 μL (0.6 mmol) acetic acid 2a, and slowly stir at 25°C for 15 minutes.

[0037] (2) Quickly add 50 μL (0.4 mmol) of boron trifluoride diethyl ether and 90 mg (0.4 mmol) of iodosuccinimide to the reaction system of step (1), and the color of the solution will change from colorless and turbid to opaque Dark purple, stirred at 25°C for 5 minutes to react.

[0038] (3) After the reaction of step (2) finishes, the reaction system is suction filtered, and the filtrate is diluted with organic solvent methylene chloride, and the organic phase is saturated with sodium thiosulfate (Na 2 S 2 o 3 ) solution was washed once, the aqueous...

Embodiment 2

[0042] A preparation method of sialic acid-n-hexanoic acid conjugate, comprising the steps of:

[0043] (1) Weigh 134mg (0.2mmol) of fully acetyl-protected sialyl glucosinolate donor 1 and 170mg of newly activated Add MS into the reaction flask, add 4 mL redistilled dichloromethane to dissolve, under the protection of argon atmosphere, stir at 25 °C, add 75 μL (0.6 mmol) n-hexanoic acid 2b, and slowly stir at 25 °C for 15 minutes.

[0044] (2) (with embodiment 1).

[0045] (3) After the reaction of step (2) finishes, the reaction system is suction filtered, and the filtrate is diluted with organic solvent methylene chloride, and the organic phase is saturated with sodium thiosulfate (Na 2 S 2 o 3 ) solution was washed once, the aqueous phase was extracted three times with organic solvent dichloromethane, then the organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and spin-dried, and eluted through silica gel column chromatography (petroleu...

Embodiment 3

[0049] A preparation method of sialic acid-5-hexynoic acid conjugate, comprising the steps of:

[0050] (1) Weigh 134mg (0.2mmol) of fully acetyl-protected sialyl glucosinolate donor 1 and 170mg of newly activated Add MS to the reaction flask, add 4 mL redistilled dichloromethane to dissolve, stir at 25°C under argon atmosphere, add 66 μL (0.6 mmol) 5-hexynoic acid 2c, and slowly stir at 25°C for 15 minutes.

[0051] (2) (with embodiment 1).

[0052] (3) After the reaction of step (2) finishes, the reaction system is suction filtered, and the filtrate is diluted with organic solvent methylene chloride, and the organic phase is saturated with sodium thiosulfate (Na 2 S 2 o 3 ) solution was washed once, the aqueous phase was extracted three times with organic solvent dichloromethane, then the combined organic phases were washed with anhydrous sodium sulfate (Na 2 SO 4 ), filtered and spin-dried, and eluted by silica gel column chromatography (ratio of petroleum ether to et...

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Abstract

The invention discloses a sialic acid-carboxylic acid compound conjugate and a preparation method thereof. The sialic acid-carboxylic acid compound conjugate is obtained by subjecting a sialic acid glucocinolate donor and a carboxylic acid compound to direct glycosylation reaction and is a compound with carboxylate at an anomeric position of sialic acid. The preparation method includes: (1), sequentially adding the sialic acid glucocinolate donor, a newly-activated molecular sieve and the carboxylic acid compound into a reaction container, adding redistilled dichloromethane for dissolution, and stirring for 15min at 25 DEG C under argon shield; (2), sequentially adding an activation system, boron trifluoride diethyl ether and iodosuccinimide quickly, and stirring for reaction at 25 DEG C for 5-10min; (3), filtering a reaction system, using an organic solvent to dilute, using a saturated sodium thiosulfate solution to wash an organic phase once, using the organic solvent to extract an aqueous phase for three times, merging the organic phase, using anhydrous sodium sulfate to dry, filtering, spin-drying, and using a silica gel column for chromatography and elution to obtain the sialic acid-carboxylic acid compound conjugate. By the preparation method, the sialic acid-carboxylic acid compound conjugate which is efficient can be provided to benefit society.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, and relates to a sialic acid-carboxylic acid compound conjugate, in particular to a sialic acid-carboxylic acid compound conjugate with potentially good drug efficacy and low side effects and a preparation method thereof. Background technique [0002] Sialic acid is a kind of ketoacid sugar compound, which is mainly distributed on the ends of glycolipids and glycoproteins on the surface of vertebrate cells, and is vividly called the "antenna" of carbohydrate compounds. It is also an essential component of polysialic acid in mammals and pathogenic bacteria. Because sialic acid is located at the outermost end of carbohydrates on the cell surface and has a highly functionalized negative charge under physiological conditions, sialic acid mediates a series of biological processes, such as cell adhesion, cell signal transduction, cell differentiation, neural Network maturation, pathogen re...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H13/06C07H13/08C07H1/00
CPCC07H1/00C07H13/06C07H13/08Y02P20/55
Inventor 杨友王稼哲
Owner EAST CHINA UNIV OF SCI & TECH
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