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1,3-[2H, 4H]-isoquinoline diketone derivative and preparation method and application thereof

A technology of isoquinoline dione and derivatives, which is applied in the field of biomedicine, can solve the problems such as the inability of biofilm inhibitors to provide active ingredients and structure-activity relationship, the complex composition of traditional Chinese medicine extracts, the unclear structure, etc., so as to achieve good biological inhibition. Membrane performance, good inhibitory effect, simple and efficient process

Active Publication Date: 2019-10-01
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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  • 1,3-[2H, 4H]-isoquinoline diketone derivative and preparation method and application thereof
  • 1,3-[2H, 4H]-isoquinoline diketone derivative and preparation method and application thereof
  • 1,3-[2H, 4H]-isoquinoline diketone derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1 Preparation of 3a compound

[0045] A method for preparing 1,3-[2H,4H]-isoquinolinedione derivatives, the reaction equation is as follows:

[0046]

[0047] It specifically includes the following reaction steps:

[0048] A. As shown in equation (1), 1 mol of compound b and 2 mol of compound c are mixed in 100 mol of methanol solution, and then filled with N at room temperature 2 React for 48 hours in an environment to obtain a catalyst cat;

[0049] In equation (1), R 3 Base is H or -CH 3 One of them, MeOH is methanol solution, OEt stands for ethylene terephthalate, rt stands for room temperature;

[0050] B. As shown in equation (2), 0.033 mol of compound f dibutyl azodicarboxylate and 0.1 mol of the catalyst cat obtained in step A are reacted at 25° C. for 30 minutes, and then 0.03 mol of compound e is added in the second Reacted in the environment of methyl chloride solution for 48 hours to obtain a solution. The solution was evaporated to a solid through an evapora...

Embodiment 2

[0058] Different from Example 1, R 2 Group is benzyl, R group is -CH 3 , R 1 The group is H and compound g gives compound 3b. The properties, optical rotation, mass spectrometry and high performance liquid chromatography of the product of compound 3b are all tested as follows:

[0059] (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):

[0060] White solid, 17.4mg, 99% yield.mp: 149.0-149.4°C;

[0061] Optical rotation:[α]17.1D=-32.94(c 0.7,CHCl 3 );

[0062] HRMS(ESI-TOF)m / z:[M+Na] + calculated for C 33 H 37 N 3 O 7 Na 610.2529,found610.2529;

[0063] 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

[0065] Different from Example 1, R 2 Group is benzyl, R group is acetyl, R 1 The group is H and compound g gives compound 3c. The properties, optical rotation, mass spectrometry and high performance liquid chromatography of the product of compound 3c are all tested as follows:

[0066] White solid, 17.0mg, 99% yield.mp: 175.8-177.5℃;

[0067] Optical rotation:[α]17.4D=+10.13(c 0.4,CHCl 3 );

[0068] HRMS(ESI-TOF)m / z:[M+Na] + calculated for C 33 H 37 N 3 O 6 Na 594.2580,found594.2571;

[0069] 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 particularly relates to a 1,3-[2H, 4H]-isoquinoline diketone derivative and a preparation method and application thereof. The structural general formula of the 1,3-[2H, 4H]-isoquinoline diketone derivative is shown in a general formula (1). The R group is one or two of H, F, Cl, Br, -CH3, -OCH3, methylthio, ethyl, amidogen and acetyl; the R1 group is one or two of H, F, Cl, Br, -CH3, -OCH3, methylthio, ethyl, amidogen and acetyl; the R2 group is one of -CH3, ethyl, acetyl, benzyl, allyl and phenyl. The 1,3-[2H, 4H]-isoquinoline diketone derivative has a good inhibition function on an acinetobacter baumannii colony sensing system, the danger of acinetobacter baumannii is greatly reduced, the preparation method is simple, and the preparedproduct can be used as a biofilm inhibitor and applied to preparation of anti-infection chiral drugs.

Description

Technical field [0001] 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. Background technique [0002] Acinetobacter baumannii (Acinetobacter baumannii) is a non-fermented gram-negative bacillus. Its powerful ability to acquire drug resistance and clonal dissemination has attracted worldwide attention. Widely and comprehensively drug-resistant Acinetobacter baumannii It has also been repeatedly reported that 58% of the strains show multi-drug resistance. Acinetobacter baumannii is also one of the main pathogenic bacteria of nosocomial infections, 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 been a serious problem that plagues major hospitals and needs to be solved urgently. In recent years, clinical practice and research results at home an...

Claims

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Application Information

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Patent Type & Authority Applications(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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