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1-phenyl-5-amino-4-pyrazole bi-oxadiazole thioether compounds and application thereof

A technology of pyrazole-linked oxadiazole sulfide and compound, which is applied in the field of medicinal chemistry, can solve the problems of complex virus replication, infection and transmission mechanism, harm, aggravated accumulation of poison sources and large-scale diffusion, and achieve blunt Significant chemical effect, significant effect, good therapeutic effect

Active Publication Date: 2018-04-06
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 virus diseases, which aggravates the accumulation and Large-scale spread has brought extremely serious and widespread harm to agricultural production, and is a major problem in the prevention and control of agricultural biological disasters

Method used

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  • 1-phenyl-5-amino-4-pyrazole bi-oxadiazole thioether compounds and application thereof
  • 1-phenyl-5-amino-4-pyrazole bi-oxadiazole thioether compounds and application thereof
  • 1-phenyl-5-amino-4-pyrazole bi-oxadiazole thioether compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Example 1: Preparation of 1-phenyl-4-((5-methylthio)-1,3,4-oxadiazolyl)-5-amino-1H-pyrazole (I1)

[0015] 1) Preparation of 1-phenyl-5-amino-1H-4-pyrazole hydrazide

[0016]

[0017] In a 250mL three-necked flask with a condenser and a thermometer, add ethyl ethoxymethylene acetate (62.1mmol), phenylhydrazine (93.2mmol), and ethanol (50mL) in sequence, heat to 80°C, react for 24h, and detect by TLC After the reaction was completed, lower it to normal temperature, distill off the solvent under reduced pressure, and dissolve the remaining solid in absolute ethanol (200mL) without purification, slowly add 80% hydrazine hydrate solution (100mmol) into the reaction solution, heat to reflux for 2 hours, and detect the reaction by TLC After the end, the system was lowered to normal temperature, suction filtered, the solid was washed with ethanol and dried to obtain the product, a white solid, with a yield of 70.5%.

[0018] 2) Preparation of 5-(5-amino-1-phenyl-1H-pyrazol-...

Embodiment 2

[0024] Embodiment 2: Preparation of 1-phenyl-4-((5-isopropyl)-1,3,4-oxadiazolyl)-5-amino-1H-pyrazole (I4):

[0025] Step (1) and (2) are with embodiment 1;

[0026] (3) Preparation of 1-phenyl-4-((5-isopropyl)-1,3,4-oxadiazolyl)-5-amino-1H-pyrazole (I4):

[0027]

[0028] In a 25mL reaction flask, add 5-(5-amino-1-phenyl-1H-pyrazol-4-yl)-1,3,4-oxadiazole-2-thiol (1.6mmol), Isobromopropane (1.6mmol) and 50% potassium hydroxide aqueous solution (20mL), stirred at room temperature, reacted for 24 hours, the reaction was detected by TLC, filtered to obtain a crude product, and column chromatography (dichloromethane / ethyl acetate=20 : 1) purification, target compound I4, white solid, yield 84.2%, melting point 88~89 ℃.

Embodiment 3

[0029] Embodiment 3: Preparation of 1-phenyl-4-((5-benzyl)-1,3,4-oxadiazolyl)-5-amino-1H-pyrazole (I28):

[0030] Step (1) and (2) are with embodiment 1;

[0031] (3) Preparation of 1-phenyl-4-((5-benzyl)-1,3,4-oxadiazolyl)-5-amino-1H-pyrazole (I28):

[0032]

[0033] In a 25mL reaction flask, add 5-(5-amino-1-phenyl-1H-pyrazol-4-yl)-1,3,4-oxadiazole-2-thiol (1.6mmol), Benzyl bromide (1.6mmol) and 50% potassium hydroxide aqueous solution (20mL), stirred at room temperature, reacted for 24 hours, the reaction was detected by TLC, filtered to obtain a crude product, and column chromatography (dichloromethane / ethyl acetate=20: 1) Purification, the target compound I28 is a white solid with a yield of 90.0% and a melting point of 164-165°C.

[0034] Through the similar synthetic method in embodiment 1, 2 and 3, the structure of the synthetic part 1-phenyl-5-amino-4-pyrazole bisoxadiazole sulfide compound and proton nuclear magnetic resonance spectrum, carbon spectrum and mass ...

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Abstract

The invention discloses a preparation method for 1-phenyl-5-amino-4-pyrazole bi-oxadiazole thioether compounds and an application in tobacco mosaic virus resistant activity. The compounds have structures represented by a general formula (I) in the description. The method provided by the invention is based on a 5-amino-1-(3-chloro-2-pyridyl)-4-(5-methylthio-1,3,4-oxadiazole-2-yl)-pyrazole structureand uses ''phenyl'' to replace ''3-chloro-2-pyridyl'' on the 1-position of a pyrazole ring to synthesize a series of the 1-phenyl-5-amino-4-pyrazole bi-oxadiazole thioether compounds, and experimentsof the compounds in vivo show that the compounds have good curative protective and inactivating activity on virus diseases caused by the tobacco mosaic virus (TMV), and the compounds show significanteffects on passivation effects compared with compounds reported in the earlier work of a research group; and the compounds provide an important scientific basis for the research, development, 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 class of 1-phenyl-5-amino-4-pyrazole bisoxadiazole sulfide compounds and an application of 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, Tobacoomosaic virus (TMV) is a typical Tobamovirus (tobamovirus) virus, which can infect a series of Solanaceae plants 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 effectivel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/04A01N43/824A01P1/00
CPCA01N43/82C07D413/04
Inventor 吴志兵杨文清周翔杨松
Owner GUIZHOU UNIV
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