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Triazole-based compound and preparation method thereof

A technology of triazoles and compounds, which is applied in the field of preparation of drugs against wheat sheath blight pathogens, and achieves the effects of simple and easy reaction operation, large profit margin and high reaction yield

Inactive Publication Date: 2018-10-16
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, with the widespread application of broad-spectrum antibiotics, hormones, and immunosuppressants, the spread of AIDS, and the popularization and application of organ transplantation and interventional techniques, the incidence of microbial infections such as fungi and bacteria has shown an upward trend, and infectious strains have also occurred. The reports of drug-resistant strains have gradually increased, and the treatment of fungal and bacterial infections is facing severe challenges

Method used

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  • Triazole-based compound and preparation method thereof
  • Triazole-based compound and preparation method thereof
  • Triazole-based compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Add CuO (0.0398g, 0.5mmol), potassium carbonate (0.691g, 5mmol), 1,2,4-triazole (0.518g , 7.5mmol), 3,4,5-tris(4-bromophenyl)-1H-1,2,4-triazole (0.498g, 1mmol), 20mL DMF. Start stirring and react at 150° C. for 48 hours. After the reaction, the reaction solution was lowered to room temperature at 20-25 degrees Celsius, filtered, and 50 mL of water was added to the filtrate, a large amount of precipitate was precipitated, filtered with suction, the filter cake was collected, and recrystallized with ethanol to obtain 3,4,5-tris(4-(1H -1,2,4-triazol-1-yl)phenyl)-4H-1,2,4-triazole single crystal, yield 68.8%. Nuclear Magnetic Spectrum-Proton Spectrum, High-resolution Mass Spectrum, please refer to figure 1 , figure 2 .

[0031] It can be seen from the hydrogen spectrum 1 H NMR (400MHz, CDCl 3 )δ: 7.35-7.40 (d, 2H, Ar-H), 7.55-7.63 (d, 4H, Ar-H), 7.66-7.78 (d, 4H, Ar-H), 7.88-7.90 (d, 2H, Ar-H),8.05-8.10(s,2H,N=CH-N),8.12-8.15(s,1H,N=CH-N),8.50-8.65(s,2H,N=CH-N), 8....

Embodiment 2

[0036] Add CuO (0.0398g, 0.5mmol), potassium carbonate (0.691g, 2.5mmol), triazole (0.518g, 4.5mmol), 3,4,5-Tris(4-bromophenyl)-1H-1,2,4-triazole (0.498 g, 1 mmol), 20 mL DMF. Start stirring at 120°C and react for 36 hours. After the reaction, the reaction solution was cooled to room temperature, filtered, and 50 mL of water was added to the filtrate, a large amount of precipitate was precipitated, filtered by suction, and the filter cake was collected, with a yield of 70%. Use the same test method to detect, showing the characteristic peaks that are basically the same as those in the nuclear magnetic spectrum and mass spectrum in Example 1, indicating that the products are consistent, and both are 3,4,5-tri(4-(1H-1,2,4-tri Azol-1-yl)phenyl)-4H-1,2,4-triazole.

Embodiment 3

[0038] Antifungal activity of 3,4,5-tris(4-(1H-1,2,4-triazol-1-yl)phenyl)-4H-1,2,4-triazole of the present invention experiment.

[0039] Main Experimental Instruments

[0040]

[0041] main experimental materials

[0042] a. Drug to be tested: 3,4,5-tris(4-(1H-1,2,4-triazol-1-yl)phenyl)-4H-1,2,4-triazol prepared by the present invention azole.

[0043] b. Medium: potato medium (potato, agar, sucrose)

[0044] c. Species to be tested: pathogenic bacteria of wheat sheath blight (the pathogenic bacteria were collected from plant samples where the pathogenic bacteria occurred in Xiqing District, Tianjin, and separated and collected in July 2015).

[0045] d. Solvent: distilled water, DMSO

[0046] The "inhibition zone method" is used for testing, which can also be called the "colony growth diameter method" (Yang Zhihui, Zhu Jiehua, Guo Qiang, Zhang Zhiming. Preliminary study on the biological characteristics of single spore isolates of potato infestans [J]. . Mycosystem,...

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Abstract

The invention discloses a triazole-based compound and a preparation method thereof. The triazole-based compound is prepared by subjecting the materials: 3,4,5-tris(4-bromophenyl)-1H-1,2,4-triazole, 1,2,4-triazole, potassium carbonate and copper oxide to reaction via a one-pot process. The triazole-based compound and the preparation method thereof have the advantages that the preparation method issimple to perform, the production cost is low, environmental pollution is low, the preparation method is suitable for large-scale industrial production, and the triazole-based compound has antifungalproperty.

Description

[0001] The application of the present invention is a divisional application of the parent application "Application of triazole-based compounds in the preparation of drugs against wheat sheath blight pathogen". The application number of the parent application is 2016102788719, and the application date is April 27, 2016 day. technical field [0002] The invention belongs to the technical field of organic synthesis, and more specifically relates to the application of triazole-based compounds in the preparation of medicines against wheat sheath blight pathogens. Background technique [0003] 1,2,4-Triazole is an important nitrogen-containing five-membered heterocyclic compound, which contains three nitrogen atoms and a π-π conjugated system in the molecule, and has a strong ability to complex metal ions and form hydrogen bonds. ability, this unique structural property makes triazole compounds exhibit a wide range of biological activities and some special properties, not only wid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08
CPCA01N43/653C07B2200/13C07D249/08
Inventor 刘巨艳黄海静张鑫
Owner TIANJIN NORMAL UNIVERSITY
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