Pyrazolyloxadiazole thioether compounds, and preparation method and application thereof

A technology of pyrazole-bioxadiazole sulfide and azole-bioxadiazole sulfide, which is applied in the field of medicinal chemistry, can solve the problem of aggravating the accumulation of poisonous sources and spreading in a large area, and cannot effectively prevent and control plant virus diseases, harm, etc. problems, to achieve good therapeutic activity

Active Publication Date: 2017-03-15
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The replication, infection and transmission mechanism of viruses are extremely complex, and the existing anti-plant virus agents (Ningnanmycin, ribavirin, morpholinidine hydrochloride, etc.) cannot effectively prevent and treat plant vir

Method used

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  • Pyrazolyloxadiazole thioether compounds, and preparation method and application thereof
  • Pyrazolyloxadiazole thioether compounds, and preparation method and application thereof
  • Pyrazolyloxadiazole thioether compounds, and preparation method and application thereof

Examples

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Effect test

Embodiment 1

[0014] Example 1 of the present invention: target compound 1-(3-chloropyridin-2-yl)-N-methyl-4-(5-(methylthio)-1,3,4-oxadiazole-2 Preparation of -yl)-1H-pyrazol-5-amine

[0015] Add the intermediate 5-amino-1-(3-chloro-2-pyridyl)-4-(5-methylthio-1,3,4-oxadiazol-2-yl)- Pyrazole (1.1mmol), sodium hydride (2.27mmol) and 10mL of anhydrous tetrahydrofuran, methyl iodide (1.3mmol) were slowly added to the reactor, reacted at room temperature for 5h, TCL detected the end of the reaction, and the solvent was removed by distillation under reduced pressure. The target compound was separated and purified by column chromatography [eluent (v / v): petroleum ether / ethyl acetate=40 / 1] as a brown solid with a yield of 40.5% and a melting point of 97-98°C.

[0016] The synthesis of the target compound substituted with alkanes and alkenes refers to Example 1.

Embodiment 2

[0017] Example 2 of the present invention: target compound 1-(3-chloropyridin-2-yl)-N-benzyl-4-(5-(methylthio)-1,3,4-oxadiazole-2 Preparation of -yl)-1H-pyrazol-5-amine

[0018] Add the intermediate 5-amino-1-(3-chloro-2-pyridyl)-4-(5-methylthio-1,3,4-oxadiazol-2-yl)- Pyrazole (1.1mmol), sodium hydride (2.27mmol) and 10mL of anhydrous tetrahydrofuran, methyl iodide (1.3mmol) were slowly added to the reactor, reacted at room temperature for 5h, TCL detected the end of the reaction, and the solvent was removed by distillation under reduced pressure. The target compound was separated and purified by column chromatography [eluent (v / v): petroleum ether / ethyl acetate=40 / 1] as a white solid with a yield of 51.6% and a melting point of 154-155°C.

[0019] Refer to Example 2 for the synthesis of target compounds substituted by benzyl, substituted benzyl and heterocycles.

[0020] The structures, H-NMR, C-NMR and mass spectrometry data of some of the synthesized pyrazole-oxadiazole s...

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PUM

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Abstract

The invention discloses a preparation method for pyrazolyloxadiazole thioether compounds and application of the pyrazolyloxadiazole thioether compounds to resisting of the activity of a tobacco mosaic virus (TMV). The compounds have a structure as shown in a general formula (I) which is described in the specification. According to the invention, on the basis of a 5-amino-1-(3-chloro-2-pyridyl)-4-(5-methylmercapto-1,3,4-oxadiazol-2-yl)pyrazol structure, a series of the pyrazolyloxadiazole thioether compounds with a novel structure are synthesized through substitution of an amino group at position 5. Results of testing of the protection and treatment activity of the compounds to the TMV show that the compounds have good treatment activity to viral diseases caused by the TMV and lay an important scientific foundation for research, development and creation of novel pesticides.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a preparation method of a pyrazole-linked oxadiazole sulfide compound and an application of its anti-tobacco mosaic virus activity. Background technique [0002] Plant virus disease is one of the serious diseases that endanger agricultural production, and the loss of crops due to plant virus disease is about 20 billion US dollars every year in the world. Due to the absolute parasitic nature of viruses in the host body, the prevention and treatment of plant virus diseases is more difficult. Among them, Tobacoo mosaic virus (TMV) is a typical Tobamovirus (tobamovirus) virus, which can infect a series of Solanaceae represented by tobacco. The replication, infection and transmission mechanism of viruses are extremely complex, and the existing anti-plant virus agents (Ningnanmycin, ribavirin, morpholinidine hydrochloride, etc.) cannot effectively prevent and treat plant v...

Claims

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Application Information

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IPC IPC(8): C07D413/14A01N43/824A01P1/00
CPCA01N43/82C07D413/14
Inventor 吴志兵杨松杨文清周翔王培义
Owner GUIZHOU UNIV
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