Lycorinine derivative as well as pharmaceutical composition and application thereof

A technology of lycorine and derivatives, which is applied in the field of medicine and can solve problems such as unclear mechanism of action

Active Publication Date: 2020-02-07
SHANDONG DYNE MARINE BIOTECHCAL PHARM HLDG CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, scholars at home and abroad have conducted further research on the antiviral effect of lycorine, and found that lycorine can significantly inhibit the replication of HIV-1 virus, and lycorine has anti-human acute respiratory syndrome-associated coronavirus (SARS- CoV), but its mechanism of action is still unclear and needs further study

Method used

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  • Lycorinine derivative as well as pharmaceutical composition and application thereof
  • Lycorinine derivative as well as pharmaceutical composition and application thereof
  • Lycorinine derivative as well as pharmaceutical composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0109] Example 1: 1-phenoxyacetyl-lycorine (1)

[0110]

[0111] 1-a: Lycorine (1.0mmol), TBSCl (2.0mmol), AgNO 3 (4.0mmol), TEF (4.0mmol), 15ml DMF, placed in a 50ml reaction bottle, stirred at room temperature in the dark until no raw materials remained. Filter, transfer the filtrate to a separatory funnel, add 50ml of dichloromethane, wash the organic phase with saturated sodium bicarbonate solution, water, and saturated sodium chloride solution, dry over anhydrous sodium sulfate, and concentrate to obtain 2-TBS-lycorine .

[0112] 1-b: Put the above-mentioned 2-TBS-lycorine, phenoxyacetic acid (1.0mmol), EDCI (1.2mmol), DMAP (0.1mmol), 15ml of dichloromethane in a 50ml reaction bottle, and stir at room temperature until the raw material Nothing left. Transfer to a separatory funnel, add 50ml of dichloromethane, wash the organic phase with saturated sodium bicarbonate solution, water, and saturated sodium chloride solution, dry over anhydrous sodium sulfate, and conce...

Embodiment 2

[0114] Example 2: 1-Phenylthioacetyl-lycorine (2)

[0115]

[0116] 2-a: Put 2-TBS-lycorine (1.0mmol), phenylthioacetic acid (1.2mmol), EDCI (1.2mmol), DMAP (0.12mmol), 15ml of dichloromethane in a 50ml reaction flask at room temperature Stir until no ingredients remain. Transfer to a separatory funnel, add 50ml of dichloromethane, wash the organic phase with saturated sodium bicarbonate solution, water, and saturated sodium chloride solution, dry over anhydrous sodium sulfate, and concentrate for later use.

[0117] 2-b: The above product, TBAF (2.0mmol), 15ml THF, was placed in a 50ml reaction bottle, and stirred at room temperature until no raw material remained. Transfer to the separatory funnel, add 50ml dichloromethane, wash the organic phase with saturated sodium bicarbonate solution, water, saturated sodium chloride solution respectively, dry over anhydrous sodium sulfate, concentrate, and separate by column chromatography to obtain a yellow solid (32.0% ). 1 H N...

Embodiment 3

[0118] Example 3: 1-(4-Chloro-phenoxyacetyl)-lycorine (3)

[0119]

[0120] 3-a: Put 2-TBS-lycorine (1.0mmol), 4-chloro-phenoxyacetic acid (1.2mmol), EDCI (1.2mmol), DMAP (0.12mmol), 15ml dichloromethane in 50ml for reaction In the bottle, stir at room temperature until no raw material remains. Transfer to a separatory funnel, add 50ml of dichloromethane, wash the organic phase with saturated sodium bicarbonate solution, water, and saturated sodium chloride solution, dry over anhydrous sodium sulfate, and concentrate for later use.

[0121] 3-b: The above product, TBAF (2.0mmol), 15ml THF, was placed in a 50ml reaction bottle, and stirred at room temperature until no raw material remained. Transfer to the separatory funnel, add 50ml dichloromethane, wash the organic phase with saturated sodium bicarbonate solution, water, saturated sodium chloride solution respectively, dry over anhydrous sodium sulfate, concentrate, and separate by column chromatography to obtain a yellow...

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Abstract

The invention belongs to the field of medicines and relates to a lycorinine derivative of a formula (I) shown in the description as well as a pharmaceutically acceptable salt, a preparation method, apharmaceutical composition and application thereof. The lycorinine derivative has remarkable antiviral activity and can be used to treat viral diseases such as hand, foot and mouth diseases.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a new class of lycorine derivatives, a pharmaceutical composition containing them, and an application in preparing antiviral drugs. Background technique [0002] Lycorine (Lycorine) was first a Japanese alkaloid isolated from the scales of the traditional Chinese medicine Lycoris. Biological activity studies have shown that lycorine and its derivatives have various functions such as anti-virus, anti-inflammatory, anti-tumor, anti-parasite, inhibition of acetylcholinesterase and cardiovascular protection. [0003] Lycorine has antiviral activity against a variety of RNA and DNA viruses. Gabrielsen B et al. found that lycorine showed in vitro inhibitory activity against Japanese encephalitis virus, yellow fever virus, dengue virus and other viruses. Lycorine also has an inhibitory effect on poliovirus, herpes virus, and Coxsackie virus B2. The intensity of inhibition ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/16A61K31/4745A61P31/14
CPCA61P31/14C07D491/16
Inventor 潘显道杨亚军沈珑瑛郑稳生
Owner SHANDONG DYNE MARINE BIOTECHCAL PHARM HLDG CO LTD
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