1,5-disubstituted 1,2,3-triazole sugar conjugates and their derivatives

A technology of triazole sugar and conjugate, which is applied in the field of 1,2,3-triazole sugar conjugate and achieves the effect of good application prospect

Inactive Publication Date: 2019-05-03
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Again, heterocyclic compounds containing sugar groups may have inhibitory effects on enzymes that cause certain diseases

Method used

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  • 1,5-disubstituted 1,2,3-triazole sugar conjugates and their derivatives
  • 1,5-disubstituted 1,2,3-triazole sugar conjugates and their derivatives
  • 1,5-disubstituted 1,2,3-triazole sugar conjugates and their derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Synthesis.

[0026] Take the yellow needle-like solid nitrostyrene (100mg) into a 50mL round bottom flask, then add 10mL DMF as a solvent, and then add 1-methyl-2,3-O-isopropylidene-5-azido -D-ribofuranose (171mg), copper chloride (5mg) as a catalyst, react at 100°C, TLC dot plate to monitor the reaction process, after observing the completion of the reaction under ultraviolet light, lift the reaction flask from the oil bath, Cool to room temperature, extract with ethyl acetate / water system to obtain ethyl acetate layer, concentrate under reduced pressure to obtain crude product, and finally use ethyl acetate / petroleum ether solution with a volume ratio of 1:2 as eluent, silica gel column layer Analyzed and separated 203 mg of light yellow oily liquid with a yield of 91%. The resulting light yellow oil 1a was analyzed, and its proton nuclear magnetic resonance spectrum and carbon spectrum were as follows: 1 H NMR(600MHz, CDCl 3 )δ7.73(s,1H),7.52(m,J=8.4,2.0Hz,3...

Embodiment 2

[0027] Example 2: Synthesis

[0028] Take the yellow needle-like solid 2-chloro-nitrostyrene (100mg) into a 50mL round-bottomed flask, then add 10mL DMF as a solvent, and then add 1-methyl-2,3-O-isopropylene- 5-azido-D-ribofuranose (139mg), copper chloride (5mg) was used as a catalyst, and the reaction was carried out at 100°C. The reaction process was monitored by TLC dot plate. After the reaction was observed under UV light, the reaction flask was removed from the oil Lift in a bath, cool to room temperature, extract with ethyl acetate / water system to obtain ethyl acetate layer, concentrate under reduced pressure to obtain crude product, and finally use ethyl acetate / petroleum ether solution with a volume ratio of 1:2 as elution Reagent, silica gel column chromatography to obtain 170mg of light yellow oily liquid, yield 88%, 1 H NMR(600MHz, CDCl 3 )δ7.59(d,J=1.8Hz,1H), 7.58(s,1H), 7.42(m,J=2.4Hz,1H), 7.41(d,J=1.8Hz,1H), 4.93(s, 1H), 4.78 (d, J = 6.0 Hz, 1H), 4.60 (d, J = 6.0 ...

Embodiment 3

[0029] Example 3: Synthesis

[0030] Take the yellow powdery solid 4-methyl-nitrostyrene (100mg) into a 50mL round bottom flask, then add 10mL DMF as a solvent to it, and then add 1-methyl-2,3-O-isopropylene -5-azido-D-ribofuranose (156mg), copper chloride (5mg) as a catalyst, react at 100℃, TLC dot plate to monitor the reaction process, after the completion of the reaction is observed under ultraviolet light, remove the reaction flask from Lift in an oil bath, cool to room temperature, extract with ethyl acetate / water system to obtain ethyl acetate layer, concentrate under reduced pressure to obtain crude product, and finally use ethyl acetate / petroleum ether solution with a volume ratio of 1:2 as washing Removal of the agent, silica gel column chromatography to obtain 180mg of light yellow oily liquid, the yield is 85%, 1 H NMR(600MHz, CDCl 3 )δ7.63(s,1H), 7.24(d,J=3.0Hz,4H), 4.87(s,1H), 4.83(d,J=6.0Hz,1H), 4.56(d,J=6.0Hz, 1H), 4.52-4.49 (m, 1H), 4.39 (m, 2H), 3.20 (s, 3H), 2...

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Abstract

The invention relates to novel 1,2,3-triazole glycoconjugate, in particular to 1,5-disubstituted 1,2,3-triazole glycoconjugate and its derivatives. The glycoconjugate has a general formula shown as in formula I, wherein R1 is phenyl, substituted phenyl, naphthyl, furyl, thienyl, indolyl or styryl. The invention has the advantages that the novel 1,5-disubstituted 1,2,3-triazole glycoconjugate is obtained by an effective synthetic means, filling the gap in the study on 1,2,3-triazole glycoconjugates and laying the basis for the study on the synthesis of efficient bioactive 1,2,3-triazole glycoconjugates; by butting triazole and glycosyl, a water solvent of triazole compounds is improved, efficiently antibacterial 1,2,3-triazole glycoconjugate with antivirus activity is obtained, and the glycoconjugate has a promising application prospect in terms of medicine.

Description

Technical field [0001] The present invention relates to a new type of 1,2,3-triazole sugar conjugates, in particular to 1,5-disubstituted 1,2,3-triazole sugar conjugates and derivatives thereof. Background technique [0002] 1,2,3-triazole is an important class of heterocyclic compounds. Because of its special physical and chemical properties, for example, 1,2,3-triazole ring is an isostere of amide bond, which is very important for metabolic degradation and redox. It has good stability under acid and alkaline conditions, and can participate in hydrogen bonding. These properties make the triazole ring conducive to the binding of biomolecular targets, and at the same time improve the solubility of molecules, so it is used in agriculture, medicine, Life sciences, materials science, organic synthetic chemistry and other fields have a wide range of applications. It has been found that some 1,2,3-triazoles have very good biological activities in medicine. Therefore, 1,2,3-triazole rin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/056C07H1/00A61P31/00A61P31/12
CPCC07H1/00C07H19/056
Inventor 陈云峰张琪
Owner WUHAN INSTITUTE OF TECHNOLOGY
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