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3-(2-aminothiazole)-7-substituted piperazine quinolone compound and its preparation method and application

A technology of aminothiazoles and compounds, applied in the field of chemical synthesis, can solve problems such as drug resistance, and achieve the effect of solving drug resistance

Active Publication Date: 2021-03-23
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to long-term widespread use and even abuse of such drugs, serious drug resistance problems have been caused, making anti-infection treatment face severe challenges

Method used

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  • 3-(2-aminothiazole)-7-substituted piperazine quinolone compound and its preparation method and application
  • 3-(2-aminothiazole)-7-substituted piperazine quinolone compound and its preparation method and application
  • 3-(2-aminothiazole)-7-substituted piperazine quinolone compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Embodiment 1, the preparation of intermediate IX

[0055]

[0056] Using triethyl orthoformate as the starting material, after nucleophilic substitution and cyclization, the latter undergoes N-alkylation, bromination, and ring closure with thiourea to obtain the 3-(2-aminothiazole)quinolone intermediate, Reference "Cui, S.F.; Addla, D.; Zhou, C.H. Novel 3-Aminothiazolquinolones: Design, Synthesis, Bioactive Evaluation, SARs, and Preliminary Antibacterial Mechanism. J. Med. Chem. 2016, 59, 4488–4510." method for preparation. 5.262 g of intermediate IX are obtained, yield 84.3%; yellow powder.

Embodiment 2

[0057] Embodiment 2, the preparation of intermediate X

[0058]

[0059] Anhydrous piperazine (3.874g, 45.0mmol) was added in a 150mL round bottom flask, and after stirring for 1 hour at 100°C with 30mL N-methylpyrrolidone as a solvent, quinolone intermediate IX (4.857g, 15.0mmol) was added, and then Adjust the temperature to 130° C. and stir the reaction, trace with thin-layer chromatography until the end of the reaction, and cool to room temperature. The mixture was poured into ice water, followed by post-processing such as filtration, column chromatography, recrystallization, and drying to obtain compound X (1.193g), yield 21.3%; yellow solid; melting point: >250°C.

Embodiment 3

[0060] Embodiment 3, the preparation of intermediate VIII

[0061] The intermediates VIII-1, VIII-2, VIII-3 and VIII-4 can be obtained by N-amidation of different types of aliphatic amine compounds and chloroacetyl chloride.

[0062]

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Abstract

The invention relates to a 3-(2-aminothiazole)-7-substituted piperazine carbostyril compound and a preparation method and the application of the 3-(2-aminothiazole)-7-substituted piperazine carbostyril compound, the 3-(2-aminothiazole)-7-substituted piperazine carbostyril compound is as shown in the general formula I-VII, and the compound has certain inhibitory activity on gram positive bacteria,gram-negative bacteria and fungus, can be used to prepare antibacterial and / or antifungal medicines, and also can be used as a DNA intercalator. The preparation raw materials are simple and cheap andare easy to obtain, and the compound is of great significance in the anti-infection application.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and relates to a 3-(2-aminothiazole)-7-substituted piperazine quinolone compound, and also relates to a preparation method and application of the compound. Background technique [0002] Bacterial infection is the main cause of most hospital-acquired infections, causing high morbidity and mortality every year, and has become an increasingly serious threat to human health. Quinolones, as the most important first-line broad-spectrum antibacterial drugs synthetically, have strong antibacterial power, less toxic and side effects, unique mechanism of action, good pharmacokinetics, convenient administration, and no cross-resistance with other commonly used antibacterial drugs. It has been widely used to treat infections caused by various pathogenic microorganisms, including urinary system infections, respiratory tract infections, prostatitis, pneumonia and acute bronchitis and other infectious diseases...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/04C07D417/14A61K31/496A61P31/04A61P31/10
CPCA61P31/04A61P31/10C07D417/04C07D417/14Y02A50/30
Inventor 周成合王亮亮巴绨倪·纳塞亚
Owner SOUTHWEST UNIV