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Substituted benzoyl piperazine compound and application thereof in preparation of anti-chikungunya virus drug

A technology of chikungunya virus and benzoylpiperazine is applied in the field of medicine to achieve the effects of good anti-CHIKV effect, good CHIKV effect and inhibition of CHIKV effect

Active Publication Date: 2021-02-02
THE NAVAL MEDICAL UNIV OF PLA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, there are no approved vaccines or specific antiviral drugs for Chikungunya fever, and the main treatments are antipyretic, analgesic and other symptomatic treatments

Method used

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  • Substituted benzoyl piperazine compound and application thereof in preparation of anti-chikungunya virus drug
  • Substituted benzoyl piperazine compound and application thereof in preparation of anti-chikungunya virus drug
  • Substituted benzoyl piperazine compound and application thereof in preparation of anti-chikungunya virus drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Preparation of Compound 1B-1:

[0042]

[0043] 3,4,5-trimethoxybenzoic acid (compound 1) (100.0mg, 0.5mmol) was placed in a 100ml round bottom flask, and DCM (10.0ml, dichloromethane) was added to dissolve it, and then 1- (2-Chlorophenyl)piperazine (120.0mg, 0.6mmol), DCC (124.0mg, 0.6mmol, N,N'-dicyclohexylcarboimide), DMAP (244.0mg, 2.0mmol), at room temperature After stirring for 6 h, it was observed that the solution changed from clear to cloudy, which was detected by TLC (DCM:MeOH=10:1), and the reaction was completed. After filtration, the filtrate was evaporated to dryness under reduced pressure and recrystallized from 95% EtOH to obtain compound 1A-1 (111.0 mg, yield: 56%).

[0044] Compound 1A-1 (100.0mg, 0.3mmol) was placed in a 100ml round-bottomed three-neck flask, and anhydrous DCM (10.0ml) was added under the protection of anhydrous and oxygen-free argon. Add BBr at a constant rate of two drops per second 3 DCM solution (6.0ml, 3.0mmol), after the d...

Embodiment 2

[0046] Preparation of compound 1B-2:

[0047]

[0048] Replace the 1-(2-chlorophenyl)piperazine used in Example 1 with 1-(3-chlorophenyl)piperazine (120.0mg, 0.6mmol), and refer to Example 1 to obtain compound 1A-2( 123.0 mg, yield: 61%). Preparation of Compound 1B-2 Refer to the preparation of Compound 1B-1 in Example 1.

Embodiment 3

[0050]

[0051] Replace the 1-(2-chlorophenyl)piperazine used in Example 1 with 1-(2,3-dichlorophenyl)piperazine (140.0mg, 0.6mmol), and refer to Example 1 to obtain compound 1A -3 (107.0 mg, yield: 58%). Preparation of Compound 1B-3 Refer to the preparation of Compound 1B-1 in Example 1.

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PUM

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Abstract

The invention discloses an application of a substituted benzoyl piperazine compound in preparation of an anti-chikungunya virus drug. The substituted benzoyl piperazine compound has a structural general formula shown in the description, wherein R1, R2, R3, R4 and R5 are respectively and independently selected from hydrogen, hydroxyl, C1-C10 alkyl, C1-C10 alkoxy and halogen, X is selected from C orN; and Y is selected from one of the groups shown in the description, and R6, R7, R8, R9, R10, R11, R12, R13, R14 and R15 are respectively and independently selected from hydrogen, hydroxyl, halogen,C1-C10 alkyl and C1-C10 alkoxy. The substituted benzoyl piperazine compound has a good CHIKV resisting effect, the cell infection rate is less than 50%, and the compound prepared by the embodiment ofthe invention has a good CHIKV inhibiting effect and can be used as an anti-chikungunya virus drug.

Description

technical field [0001] The invention belongs to the technical field of medicines, and in particular relates to a class of substituted benzoylpiperazine compounds and their application in the preparation of anti-Kungunya virus drugs. Background technique [0002] Chikungunya virus (CHIKV) is a member of the Togaviridae Alphavirus genus, and humans and non-human primates are the main hosts of CHIKV. Chikungunya virus can be called Chikungunya fever. Chikungunya fever is an acute febrile infectious disease transmitted by mosquito bites. In the past, the virus disease was mainly distributed in the tropical and subtropical regions of Africa, South Asia, and Southeast Asia. In recent years, with factors such as global warming and modern transportation, the virus epidemic has shown a trend of continuous outbreak and spread. On November 19, 2009, an imported case of Chikungunya fever was detected for the first time at Shenzhen port. After a patient is infected with Chikungunya vi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/192C07D295/185C07D211/32A61P31/14
CPCC07D295/192C07D295/185A61P31/14C07D211/18C07D317/60Y02A50/30
Inventor 金永生赵兰娟彭浩然王瀚萱马颖陈矗然赵平
Owner THE NAVAL MEDICAL UNIV OF PLA