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Triterpene-amino acid derivative as well as preparation method and application thereof

A kind of amino acid and derivative technology, applied in the field of triterpene natural amino acid derivatives

Active Publication Date: 2018-10-12
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The inhibitory effect of triterpene natural amino acid derivatives on influenza virus has not been reported

Method used

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  • Triterpene-amino acid derivative as well as preparation method and application thereof
  • Triterpene-amino acid derivative as well as preparation method and application thereof
  • Triterpene-amino acid derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0126] The synthesis of embodiment 1 oleanolic acid-valine conjugate

[0127]

[0128] Take 1 g of L-valine in a 50 ml reaction bottle, add 24 ml of methanol to dissolve it, then place the reaction bottle in an ice bath, slowly add 3 ml of thionyl chloride dropwise with a normal-pressure dropping funnel, and after the dropping Move to room temperature to react, and thin-layer detection after 3 hours, the ratio of developer: dichloromethane: methanol = 10:1, add a drop of ammonia water at the same time, and ninhydrin chromogenic reagent to develop color. Evaporate methanol and excess thionyl chloride directly to dryness, and the crude product can be directly used in the subsequent reaction without purification, but it is necessary to ensure that the product point on the thin layer is single. If the product point is not single, it needs to be purified by column chromatography.

[0129] Take 1g of oleanolic acid, dissolve it in 20ml of THF, add 844mg of TBTU and 339mg of DIEA ...

Embodiment 2

[0132] Example 2 Synthesis of oleanolic acid-histidine conjugates

[0133]

[0134] Take 1 g of L-histidine in a 50 ml reaction bottle, add 24 ml of methanol to dissolve it, then place the reaction bottle in an ice bath, slowly add 3 ml of thionyl chloride dropwise with a normal pressure dropping funnel, after the dropping Move to room temperature to react, after 3 hours TLC detection, developer ratio: dichloromethane: methanol = 10:1, add a drop of acetic acid at the same time, ninhydrin chromogenic reagent develops color. Evaporate methanol and excess thionyl chloride directly to dryness, and the crude product can be directly used in the subsequent reaction without purification, but it is necessary to ensure that the product point on the thin layer is single. If the product point is not single, it needs to be purified by column chromatography.

[0135] Take 539mg of L-histidine methyl ester hydrochloride, dissolve in THF, add 266mg of triethylamine, add 1g of oleanolic ac...

experiment example

[0140] The following are the experimental results of anti-influenza virus of some compounds of the present invention.

[0141] 1. M12 can effectively inhibit the replication of influenza virus. The CPE inhibition test and the plaque inhibition test proved that the compound M12 had a significant inhibitory effect on influenza virus, which was stronger than the positive drug ribavirin. The CPE inhibition assay showed that the EC of M12 against influenza virus 50 was 37.2µM, while the EC of the positive drug Tamiflu (oseltamivir phosphate, OSV-P) 50 EC of 41.9 µM, ribavirin (RBV) 50 is 50.3 µM (see Table 1). Plaque inhibition assays show the IC of M12 against influenza virus 50 figure 1 ). And the CC of M12 in A549, MDCK and 293T cells 50 All are greater than 100µM, indicating that the cytotoxicity of M12 is very small.

[0142] Table 1: Inhibitory activity of M12 against influenza virus (WSN) and its cytotoxicity analysis.

[0143]

[0144] a : CC 50 , the half cy...

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Abstract

The invention relates to application of a triterpene derivative in a formula in preparation of medicines for preventing or treating influenza diseases. The definition of substituent groups is shown ina description. The triterpene derivative has obvious inhibiting function on influenza viruses, and can obviously inhibit the influenza viruses from entering cells. The formula is shown in the description.

Description

technical field [0001] The present invention relates to a new application of a triterpene natural amino acid derivative, that is, its application 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 viruses can be divided into types A, B, C and D. Large-scale epidemics 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 twentieth 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 2009 was also caused by the H1N1...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61K31/56A61K31/58A61P31/16
CPCA61P31/16C07J63/008
Inventor 俞飞孟令宽杨帆李唯嘉苏扬清肖苏龙周德敏
Owner KUNMING UNIV OF SCI & TECH
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