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A 1,3-[2h,4h]-isoquinolinedione derivative and its preparation method and application

A technology of isoquinoline diones and derivatives, applied in the field of biomedicine, can solve problems such as unclear structure, complex components of traditional Chinese medicine extracts, guidance, etc., to reduce drug resistance, better inhibit biofilm performance, and better The effect of medicine

Active Publication Date: 2021-06-29
GUIZHOU MEDICAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage is that the extracts of traditional Chinese medicine have complex components and unclear structures, and cannot provide guidance on active ingredients and structure-activity relationships for the development of more effective biofilm inhibitors

Method used

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  • A 1,3-[2h,4h]-isoquinolinedione derivative and its preparation method and application
  • A 1,3-[2h,4h]-isoquinolinedione derivative and its preparation method and application
  • A 1,3-[2h,4h]-isoquinolinedione derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1 prepares 3a compound

[0048] A kind of preparation method of 1,3-[2H, 4H]-isoquinoline dione derivative, reaction equation is as follows:

[0049]

[0050] Equation (1)

[0051]

[0052] Equation (2)

[0053] Concretely comprise following reaction steps:

[0054] A, as shown in equation (1), 1mol compound b and 2mol compound c are mixed in the methanol solution of 100mol, then at room temperature and full of N 2 React in the environment of 48 hours, obtain catalyst cat;

[0055] In equation (1), R 3 The group is H or -CH 3 One of them, MeOH is a methanol solution, and rt stands for room temperature;

[0056] B, as shown in equation (2), 0.033mol of compound f di-tert-butyl azodicarboxylate and the catalyst cat obtained in 0.1mol step A reacted at 25°C for 30min, then added 0.03mol of compound e after In the environment of dichloromethane solution, react for 48 hours to obtain a solution, the solution is evaporated to a solid by an evaporator, ...

Embodiment 2

[0064] Unlike Example 1, R 2 The base is benzyl, and the R base is -CH 3 , R 1 The group is H, compound g gives compound 3b. The properties, optical rotation, mass spectrum and high performance liquid chromatography of the product of compound 3b are all tested as follows:

[0065] (S)-di-tert-butyl 1-(2-benzyl-7-methoxy-1,3-dioxo-4-phenyl-1,2,3,4-tetrahydroisoquinoline-4 -yl)hydrazine-1,2-dicarboxylate (compound 3b):

[0066] White solid, 17.4g, 99% yield.mp: 149.0-149.4℃;

[0067] Optical rotation: [α]17.1D=-32.94(c 0.7, CHCl 3 );

[0068] HRMS(ESI-TOF)m / z:[M+Na] + calculated for C 33 h 37 N 3 o 7 Na 610.2529, found 610.2529;

[0069] The enantiomeric excess was determined to be 88.55% by HPLC. [OD-Hcolumn, 230nm, n-hexane:IPA=97:3, 0.5mL / min]: 18.9min(major), 38.7min(minor);

Embodiment 3

[0071] Unlike Example 1, R 2 The base is benzyl, the R base is acetyl, and the R 1 The group is H, compound g gives compound 3c. The properties, optical rotation, mass spectrum and high performance liquid chromatography of the product of compound 3c are all tested as follows:

[0072] White solid, 17.0g, 99% yield.mp:175.8–177.5℃;

[0073] Optical rotation: [α]17.4D=+10.13(c 0.4, CHCl 3 );

[0074] HRMS(ESI-TOF)m / z:[M+Na] + calculated for C 33 h 37 N 3 o 6 Na 594.2580, found 594.2571;

[0075] The enantiomeric excess was determined to be 97.29% by HPLC. [OD-Hcolumn, 230nm, n-hexane:IPA=99:1, 1.0mL / min]: 12.6min(major), 19.5min(minor);

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Abstract

The invention belongs to the field of biomedicine, and specifically relates to a 1,3-[2H,4H]-isoquinolinedione derivative and a preparation method and application thereof. The general structural formula of the 1,3-[2H,4H]-isoquinolinedione derivatives is shown in the general formula (1), wherein the R groups are H, F, Cl, Br, -CH 3 ,-OCH 3 One or both of , methylthio, ethyl, amino and acetyl; R 1 The group is H, F, Cl, Br, -CH 3 ,-OCH 3 One or both of , methylthio, ethyl, amino and acetyl; R 2 The base is -CH 3 , ethyl, acetyl, benzyl, propenyl and phenyl in one. The 1,3-[2H,4H]-isoquinolinedione derivative of the present invention has a better inhibitory effect on the quorum sensing system of Acinetobacter baumannii, greatly reduces the harm of Acinetobacter baumannii, and is prepared The method is simple, and the prepared product can be used as a biofilm inhibitor to prepare anti-infection chiral drugs.

Description

technical field [0001] The invention belongs to the field of biomedicine, and in particular relates to a 1,3-[2H,4H]-isoquinolinedione derivative and a preparation method and application thereof. Background technique [0002] Acinetobacter baumannii (Acinetobacter baumannii) is a non-fermenting Gram-negative bacillus, and its strong ability to acquire drug resistance and clone transmission has attracted widespread attention around the world. Extensively drug-resistant and comprehensively drug-resistant Acinetobacter baumannii It has also been repeatedly reported that 58% of the strains showed multi-drug resistance. Acinetobacter baumannii is also one of the main pathogenic bacteria of nosocomial infection, especially in the intensive care unit (ICU), where the mortality rate is as high as 43%. The continuous spread and repeated attacks of the bacteria in hospitals have become a serious problem that plagues major hospitals and needs to be solved urgently. In recent years, c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D217/24C07D401/04C07D405/04C07D409/04C07B53/00A61P31/04
CPCA61P31/04C07B53/00C07B2200/07C07D217/24C07D401/04C07D405/04C07D409/04
Inventor 杨元勇汤磊杨果程铖李应贤
Owner GUIZHOU MEDICAL UNIV
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