Compound and application thereof in resistance to arenavirus infection

A compound, C1-C5 technology, used in antiviral agents, organic chemistry, etc., can solve the problems of high mortality, no vaccine, serious clinical manifestations, etc., and achieve broad-spectrum inhibitory activity and strong inhibitory effect.

Active Publication Date: 2019-03-22
TIANJIN INT JOINT ACADEMY OF BIOTECH & MEDICINE +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Lassa fever has become a new serious international infectious disease in recent years due to its acuteness, strong infectivity, serious clinical manifestations and high fatality rate. Efforts necessary to develop a safe and effective treatment for Lassa virus

Method used

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  • Compound and application thereof in resistance to arenavirus infection
  • Compound and application thereof in resistance to arenavirus infection
  • Compound and application thereof in resistance to arenavirus infection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]

[0037] The specific process is:

[0038] (1) Take a 50ml round bottom flask and add 15mL of ethanol and 1g of compound A in turn, slowly add 0.36g of NaBH to the system 4 (sodium borohydride), the system is white and turbid, and the reaction at room temperature ends after 3 hours. Use 1mol / L HCl (hydrochloric acid) to adjust the pH to 5, then remove the solvent, extract twice with water and ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, and concentrate in vacuo to obtain 1 g of a white solid, namely compound B, with a yield of 99%.

[0039] (2) Take a 50mL round bottom flask and add 3ml of dichloromethane, 0.15g of compound B, 0.16g of compound C and 0.62g of EDCI (1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride salt), 0.4g DMAP (4-dimethylaminopyridine), the system is yellow and clear, and the reaction is completed after stirring at room temperature for 5h, and then the system is respectively treated with 1mol / L HCl and ...

Embodiment 2

[0041]

[0042] The specific process is:

[0043] (1) Take a 100mL round-bottom flask and add 10mL of dichloromethane, 0.5g of p-nitrobenzyl bromide, and 0.64g of phthalamide potassium salt in turn, and stir at room temperature to react. The system is white and turbid, and then slowly turns purple. After 2 hours of reaction at room temperature, the system was extracted twice with dichloromethane and water, the organic phases were combined and dried, and 0.65 g of a yellow solid, namely compound E, was obtained by rotary evaporation, with a yield of 100%.

[0044] (2) Take a 50mL round bottom flask and add 5mL ethanol and 0.27g compound E successively. The system is yellow and turbid. After adding 3.5mL80% hydrazine hydrate, the system becomes red and turbid. After 2h reaction at room temperature, the system is concentrated in vacuum and used Ethyl acetate and water were extracted twice, the organic phases were combined and dried over anhydrous sodium sulfate, and concentrat...

Embodiment 3

[0049]

[0050] The specific process is:

[0051] Take a 50mL flask and add 3mL of dichloromethane, 0.1g of compound I, 0.12g of compound B, 0.41g of EDCI, 0.26g of DMAP, and stir the reaction system at room temperature. / L HCl and saturated NaHCO 3 After washing, the organic phase was collected and dried with anhydrous sodium sulfate, and then the solvent was removed by rotary evaporation, and 0.14 g of a yellow liquid was obtained by purification with a silica gel column, namely compound J (ie, compound 9 of the above compound), and the reaction yield was 83%.

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Abstract

The invention provides a compound and application thereof in resistance to arenavirus infection. The structural formula of the compound is as shown in the figure (I) in the specification, wherein Ar is selected from an aromatic ring or aromatic heterocycte containing a substituent group or not containing the substituent group, X is selected from a C1-C5 alkyl group, a C1-C5 alkoxy group, a C1-C5 alkyl amino group, C1-C5 alkyl thioether, a C1-C5 alkenyl group, a C1-C5 alkynyl group, a cyclopropane group, a cyclobutane group, an epoxypropane group, aziridine, a cyclopropane group or a cyclobutane group connected to the C1-C5 alkyl group, Y is selected from an oxygen atom, a secondary amino group, a tertiary amino group, a C1-C3 alkyl group or an azyloxy group(-NH-H-), and each of R1 and R2 is selected from a hydrogen atom, a C1-C5 alkyl group, a C1-C5 alkenyl group, a C1-C5 alkynyl group, a naphthenic group and an aromatic ring or aromatic heterocycte containing a substituent group or not containing the substituent group.

Description

technical field [0001] The application relates to the field of medicine, more specifically, to a compound and its application in anti-arenavirus infection. Background technique [0002] The Arenaviruses family are enveloped RNA viruses that can be systematically divided into two types: the old world Lineages and the new world Lineages. Several human pathogenic arenaviruses have been identified, including Lassa virus, lymphocytic choriomeningitis virus (LCMV), Junín virus and Machupo virus, Guanartio virus, Sabiávirus , Chapare virus and Dandenong virus. Lassa virus is an enveloped, double-segmented RNA virus belonging to the Old World group of the Arenaviridae family. The genome of Lassa virus consists of 2 single-stranded negative-strand RNAs (S and L), and the L fragment encodes Z and L proteins. The L protein is an RNA-dependent RNA polymerase that determines the efficiency of replication; the Z protein acts as a matrix protein, Plays an important role in virus budding...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/68C07D405/12C07C233/44C07C219/32A61P31/14
CPCA61P31/14C07C219/32C07C233/44C07D307/68C07D405/12
Inventor 蔡岩王薇肖庚富杨诚刘洋张光顺李燕丽任晋州张蒙蒙郭宇赵佩佩汪颖毛永红贺万丽
Owner TIANJIN INT JOINT ACADEMY OF BIOTECH & MEDICINE
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