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Pyridine salt compound containing 1,3,4-oxadiazolyl (thiadiazolyl) and preparation method and application thereof

A technology for salt compounds and pyridine, which is applied in the field of pyridine salt compounds and their preparation, and can solve the problems of reducing the bacteriostatic activity of the compounds and the like

Inactive Publication Date: 2016-05-04
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Preliminary structure-activity relationship shows that the antibacterial activity of the compound gradually decreases with the increase of the carbon chain of the R group

Method used

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  • Pyridine salt compound containing 1,3,4-oxadiazolyl (thiadiazolyl) and preparation method and application thereof
  • Pyridine salt compound containing 1,3,4-oxadiazolyl (thiadiazolyl) and preparation method and application thereof
  • Pyridine salt compound containing 1,3,4-oxadiazolyl (thiadiazolyl) and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Example 1 of the present invention: target compound 10-[5-(2,4-dichlorophenyl)-2-mercapto-1,3,4-oxadiazole]decyl ether-1-pyridinium bromide preparation

[0023] Dissolve 0.53g (1.1mmol) 2-(10-bromodecyl)mercapto-5-(2,4-dichlorophenyl)-1,3,4-oxadiazole in 5mL pyridine solvent and react at 50°C Stop the reaction after 6h, remove the solvent, and wash with ether to obtain 0.54 g of white solid, yield 87.1%, melting point: 96-98°C.

[0024] The synthesis of oxygen ether and thioether target compounds refers to Example 1.

Embodiment 2

[0025] Example 2 of the present invention: target compound 10-[2-sulfoxide-5-(2,4-dichlorophenyl)-1,3,4-oxadiazole]decyl-1-pyridinium bromide preparation of

[0026] Dissolve 0.45g of 2-(10-bromodecyl)sulfoxide-5-(2,4-dichlorophenyl)-1,3,4-oxadiazole in 5mL of pyridine, react at 50°C for 6h, and remove the solvent. Purified by column chromatography to obtain 0.42 g of light yellow solid with a yield of 80.2% and a melting point of 84-86°C.

[0027] The synthesis of sulfoxide and sulfone target compounds refers to Example 2.

[0028] The structure, H NMR spectrum and carbon spectrum data of some synthesized pyridinium salt compounds containing 1,3,4-oxa(thia)diazolyl are shown in Table 1, and their physical and chemical properties are shown in Table 2.

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[0043] Pharmacological Example 1: EC 50 (median effectiv...

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Abstract

The invention disclose a pyridine salt compound containing 1,3,4-oxadiazolyl (thiadiazolyl) and a preparation method and application thereof. The compound is of the structure shown in the general formula (I). Based on the 1,3,4- oxadiazole (thiadiazole) thioether (sulfoxide or sulfone) compound, a pyridine base capable of improving the biological activity of the target compound is introduced into the system, and a series of 1,3,4- oxadiazole (thiadiazole) oxygen ether, thioether, sulfoxide or sulfone amphipathic molecules containing pyridine salt are synthesized. It is found that the compound has the good restraining effect on pathogenic bacteria and fungi such as Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum, Xanthomonas axonopodis pv. citri, Gibberella zeae, Phytophythora infestans, Rhizoctonia solani, Borrytis cinerea, Fusarium oxysporum and Phytophythora infestans, and provides an important scientific foundation for new pesticide research, development and creation.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a 1,3,4-ox(thia)diazolyl-containing pyridinium salt compound, a preparation method and application thereof. Background technique [0002] In recent years, plant pathogenic bacteria and fungi have seriously threatened the production of food and crops in my country. In order to control bacterial and fungal diseases, it is urgent to prepare active small molecules that are highly effective against pathogenic bacteria and fungi. However, the activity of the currently used commercial antibacterial drugs is not efficient enough. Screening and searching for highly effective bactericidal active compounds is an important part of the current research and development of new pesticides. [0003] Compounds based on pyridinium salts have become one of the hotspots of researchers because of their wide range of biological activities (such as anti-gram-positive (or negative) bacteria, ...

Claims

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Application Information

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IPC IPC(8): C07D413/12C07D417/12A01P1/00A01P3/00
CPCA01N43/82C07D413/12C07D417/12
Inventor 杨松王培义周磊吴志兵胡德禹薛伟
Owner GUIZHOU UNIV
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