Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Sialic acid-carboxylic acid compound conjugate and preparation method thereof

A technology for compounds and carboxylic acids, applied in the field of medicinal chemistry, can solve the problems of low synthesis efficiency, uncontrollable product stereoselectivity, and complicated operation, and achieve the effects of high synthesis efficiency, reduced irritation, and simple operation.

Active Publication Date: 2017-07-28
EAST CHINA UNIV OF SCI & TECH
View PDF2 Cites 3 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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

[0034] A kind of preparation method of sialic acid-acetic acid conjugate, comprises the steps:

[0035] (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.

[0036] (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.

[0037] (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

[0041] A preparation method of sialic acid-n-hexanoic acid conjugate, comprising the steps of:

[0042] (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 75 μL (0.6 mmol) n-hexanoic acid 2b, and slowly stir at 25°C for 15 minutes.

[0043] (2) (with embodiment 1).

[0044] (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 (the ratio of petroleum ether t...

Embodiment 3

[0048] A preparation method of sialic acid-5-hexynoic acid conjugate, comprising the steps of:

[0049] (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.

[0050] (2) (with embodiment 1).

[0051] (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...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com