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Carbazole oxadiazole conjugates, and preparation method and application thereof

A technology of oxadiazole and carbazole, which is applied in the field of chemical synthesis, can solve the problems of poor solubility and limited application of carbazole compounds, and achieve the effects of solving drug resistance, simple preparation of raw materials, and short synthesis route

Pending Publication Date: 2019-10-15
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the planar rigid structure of carbazole, the solubility of carbazole compounds is poor, which greatly limits their further applications. Therefore, improving the water solubility and lipophilicity of carbazole compounds is the key to enhance their metabolic stability and biological activity.

Method used

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  • Carbazole oxadiazole conjugates, and preparation method and application thereof
  • Carbazole oxadiazole conjugates, and preparation method and application thereof
  • Carbazole oxadiazole conjugates, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1: the preparation of intermediate II-1:

[0043]

[0044]Stir N,N-dimethylformamide (100 mL) containing carbazole (1.000 g, 5.980 mmol) and cesium carbonate (2.530 g, 7.780 mmol) at 85 °C for 30 minutes, cool slightly, then add 2-bromo Ethyl acetate (1.300g, 7.780mmol), continue to stir the reaction at 85°C, track by thin-layer chromatography until the reaction is complete, pour the reaction mixture into ice water to precipitate a solid, suction filter, wash and dry to obtain the intermediate II-1 (1.067g), yield: 70.5%.

Embodiment 2

[0045] Embodiment 2: the preparation of intermediate II-2:

[0046]

[0047] N,N-dimethylformamide (100 mL) containing 2-bromocarbazole (1.000 g, 4.063 mmol) and cesium carbonate (1.721 g, 5.282 mmol) was stirred at 85°C for 30 minutes, cooled slightly, and then added 2-Ethyl bromoacetate (0.882g, 5.282mmol), continue to stir the reaction at 85°C, track by thin layer chromatography until the reaction is complete, pour the reaction mixture into ice water to precipitate a solid, suction filter, wash and dry, Intermediate II-2 (1.017g) was obtained, yield: 75.6%.

Embodiment 3

[0048] Embodiment 3: the preparation of intermediate II-3:

[0049]

[0050] N,N-dimethylformamide (100 mL) containing 2-chlorocarbazole (1.000 g, 4.974 mmol) and cesium carbonate (2.1071 g, 6.467 mmol) was stirred at 85°C for 30 minutes, cooled slightly, and then added 2-Ethyl bromoacetate (1.080g, 6.467mmol), continue to stir the reaction at 85°C, track by thin-layer chromatography until the reaction is complete, pour the reaction mixture into ice water to precipitate a solid, suction filter, wash and dry, Intermediate II-3 (1.104 g) was obtained with a yield of 77.3%.

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Abstract

The invention relates to carbazole oxadiazole conjugates, and a preparation method and an application thereof, and belongs to the technical field of chemical synthesis. The carbazole oxadiazole conjugates are represented by general formula I. The above compounds have a certain inhibitory activity to one or more of Gram-positive bacteria, Gram-negative bacteria and fungi, and can be used to prepareantibacterial and / or antifungal drugs in order to provide efficient and safe drug candidate drugs for clinical ant-microbial treatment and contribute to solve clinical treatment problems such as increasing drug resistance, stubborn pathogenic microorganisms and emerging harmful microorganisms. The carbazole oxadiazole conjugates have the advantages of simple, cheap and easily available preparation raw materials, short synthesis route, and great meaning in the anti-infection field.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a carbazole-type oxadiazole conjugate and a preparation method and application thereof. Background technique [0002] The rapid spread of drug-resistant strains has seriously affected the antibacterial efficiency of many clinical antibacterial drugs. In the past few decades, the significant increase in the number of fungal infections in immunocompromised populations has forced researchers to accelerate the pace of research and development of new antibacterial drugs. The emergence of antimicrobial drugs, especially azoles, has opened up a new era of microbial drug treatment. Since the first azole antibacterial drug clotrimazole was used in clinical practice, azoles have attracted widespread attention. At the same time, with the increasing application of azole drugs, the problem of microbial resistance is becoming more and more serious. Among them, the mechan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/06A61P31/04A61P31/10
CPCC07D413/06A61P31/04A61P31/10Y02A50/30
Inventor 周成合谢云鹏
Owner SOUTHWEST UNIVERSITY
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