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Triterpene-oligosaccharide conjugates and application thereof

A technology of conjugates and oligosaccharides, used in steroids, medical preparations containing active ingredients, organic chemistry, etc.

Active Publication Date: 2019-01-18
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Triterpene carbohydrate derivatives of the present invention and its inhibitory effect on influenza virus have not been reported

Method used

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  • Triterpene-oligosaccharide conjugates and application thereof
  • Triterpene-oligosaccharide conjugates and application thereof
  • Triterpene-oligosaccharide conjugates and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Example 1: The preparation method of this triterpene-oligosaccharide conjugate, taking the preparation of M8 compound as an example, the synthetic route is as follows:

[0064]

[0065] The concrete preparation technology of M8 compound is as follows:

[0066] (a) Take 1g of L-rhamnose in a 100mL reaction bottle, add 30mL of pyridine to dissolve it, then place the reaction bottle in an ice bath, slowly add 10.5mL of acetic anhydride with a normal pressure dropping funnel, and transfer to Reaction at room temperature, TLC detection after 3h, developer petroleum ether: ethyl acetate = 1:1, CMC chromogenic reagent for color development. Pyridine and excess acetic anhydride were directly evaporated to dryness to obtain compound M30; the crude product could be directly used in subsequent reactions without purification, but it was necessary to ensure that the product point on the thin layer was single, and if the product point was not single, purification by column chromat...

Embodiment 2

[0097] Embodiment 2: The compound of the present invention inhibits the biological activity evaluation method of influenza virus entering cells

[0098] 1. Cytopathic Efficacy (CPE) Inhibition Test

[0099] After influenza virus infects cells, it will cause cell pathology, which will reduce cell viability; if the drug can inhibit the replication of influenza virus, it will reduce the number of cell lesions and increase cell viability; the specific method is as follows:

[0100] (1) Canine kidney epithelial cells (MDCK) were passaged into a white 96-well plate at a ratio of 1:3, and cultured in DMEM medium containing 10% FBS for 24 hours in a cell culture incubator at 37°C;

[0101] (2) Add influenza virus [A / WSN / 33 (H1N1), multiplicity of infection (MOI) = 1] and 100 μM / L of the compound to be tested to 100 μl of DMEM containing 2 μg / mL TPCK-treated trypsin and 1% FBS Mix well; the negative control of the compound is 1% DMSO (the solvent used for diluting the compound); set u...

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Abstract

The invention discloses triterpene-oligosaccharide conjugates, the structural formulae of which are as shown in a formula, and an application thereof in preparing drugs for treating and / or preventingflu. Experimental results display that the triterpene-oligosaccharide conjugates have an obvious inhibiting effect to flu viruses and can prevent the flu viruses from entering cells obviously. The compounds can inhibit flu virus infection from the source, thereby providing a ground for researching an anti-flu virus inhibitor.

Description

technical field [0001] The invention relates to a class of triterpene-oligosaccharide conjugates and applications thereof, that is, their use in preventing or treating influenza. Background technique [0002] Influenza is an acute, contagious respiratory disease caused by influenza virus. According to the antigenicity of its internal nucleoprotein (NP) and matrix protein (M), influenza virus can be divided into A type, B type, C type and D type. The large-scale epidemic of type A (also known as type A) influenza virus can cause extremely high morbidity and mortality, which seriously threatens human health (Virology Journal. 2007, 4, 1-5). Influenza A virus mainly caused three major influenzas in the 20th century, namely H1N1 in 1918, H2N2 in 1957 and H3N2 in 1968, causing a total of about 50 million deaths (Emerging Infectious Diseases. 2006, 12, 9-14; Journal of the American Medical Association, 2007, 18, 2025-2027). Influenza A in 2009 was also caused by H1N1 influenza ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/7056A61P31/16
CPCA61P31/16C07J63/008
Inventor 俞飞孟令宽杨帆李唯嘉苏扬清邵亮周德敏
Owner KUNMING UNIV OF SCI & TECH
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