2-substituted sulfinyl-5-(3,4,5-trialkoxy phenyl)-1,3,4-oxadiazole derivatives as well as preparation method and uses thereof

A substituent, alkylsulfonyl technology, applied to 2-substituted sulfinyl-5-(3,4,5-trialkoxyphenyl)-1,3,4-oxadiazole derivatives And the field of preparation and application, can solve the problem of unsatisfactory antibacterial activity, achieve the effect of good activity

Inactive Publication Date: 2008-09-03
GUIZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The results showed that the antibacterial activity of the compound was not satisfactory

Method used

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  • 2-substituted sulfinyl-5-(3,4,5-trialkoxy phenyl)-1,3,4-oxadiazole derivatives as well as preparation method and uses thereof
  • 2-substituted sulfinyl-5-(3,4,5-trialkoxy phenyl)-1,3,4-oxadiazole derivatives as well as preparation method and uses thereof
  • 2-substituted sulfinyl-5-(3,4,5-trialkoxy phenyl)-1,3,4-oxadiazole derivatives as well as preparation method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Example 1, 2-(benzylsulfinyl)-5-(3,4,5-trimethoxy)phenyl-1,3,4-oxadiazole (the compound number is a)

[0052] (1) Synthesis of N-(3,4,5-trimethoxy) potassium benzoylhydrazine dithioformate

[0053] Weigh 6.8g (0.030mol) of 3,4,5-trimethoxybenzoic hydrazide into a 500mL three-neck round bottom flask, add 200mL of absolute ethanol, add 2g (0.036mol) of potassium hydroxide, and stir to dissolve . Control the temperature to room temperature, add 2.28g (0.030mol) carbon disulfide dropwise, and stir rapidly for 5h. Suction filtration and washing with absolute ethanol gave a white solid. Recrystallize from methanol to obtain white crystals, which are potassium N-(3,4,5-trimethoxy)benzoylhydrazinodithioformate. The melting point is 214-216°C, and the yield is 73.7%.

[0054] (2) Synthesis of 2-mercapto-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole

[0055] Under an ice-salt bath, pipette 10 mL of sulfuric acid into a 50 mL three-neck round bottom flask. 2 g (0.0059 mol) of ...

Embodiment 2

[0060] Embodiment two, the synthesis of 2-(3-methoxybenzylsulfinyl)-5-(3,4,5-trimethoxy)phenyl-1,3,4-oxadiazole (the compound number is b)

[0061] (1) Synthesis of potassium N-(3,4,5-trimethoxy)benzoylhydrazinodithioformate was synthesized according to the method and conditions of Example 1 (1).

[0062] (2) Synthesis of 2-mercapto-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole was synthesized according to the method and conditions of Example 1 (2).

[0063] (3) Synthesis of 2-(3-methoxybenzyl)thio-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole

[0064]Weigh 2-mercapto-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole (35mmol) and 3-methoxybenzyl chloride (40mmol) into 100mL three ports In a round bottom flask, add 30 mL of acetone (re-distilled, dried with anhydrous calcium chloride) and 12 mL of pyridine, stir, and add dropwise 4 mL of triethylamine (re-distilled, dried with potassium hydroxide) and 20 mL of acetone in an ice bath The mixed solution was added dropwise in 10 minutes,...

Embodiment 3

[0067] Example 3, 2-(3-fluorobenzylsulfinyl)-5-(3,4,5-trimethoxy)phenyl-1,3,4-oxadiazole (compound number is c)

[0068] (1) Synthesis of potassium N-(3,4,5-trimethoxy)benzoylhydrazinodithioformate was synthesized according to the method and conditions of Example 1 (1).

[0069] (2) Synthesis of 2-mercapto-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole was synthesized according to the method and conditions of Example 1 (2).

[0070] (3) Synthesis of 2-(3-fluorobenzyl)thio-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole

[0071] Weigh 2-mercapto-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole (35mmol) and 3-methoxybenzyl chloride (40mmol) into 100mL three ports In a round bottom flask, add 30 mL of acetone (re-distilled, dried with anhydrous calcium chloride) and 12 mL of pyridine, stir, and add dropwise 4 mL of triethylamine (re-distilled, dried with potassium hydroxide) and 20 mL of acetone in an ice bath The mixed solution was added dropwise in 10 minutes, and the reaction was contin...

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Abstract

The invention disclose 2-substituted sulfinyl-5-(3, 4, 5-trialkoxyphenyl)-1, 3, 4oxdiazole series derivates which are a medicine for restraining pathogenic bacteria of vegetables, fruits and chinese herbal medicines, a preparation method and bioactivity, wherein the compounds are represented by the followed general formula. The compounds can be synthesized by four steps, using 3, 4, 5-trialkoxyl benzoyl hydrazine, carbon disulphide, alkalis, RX as raw materials, using water, alcohols, N, N-dimethylformamide, propanone, dioxygen hexacyclic ring, dimethyl sulfoxide as dissolvants, using triethylamine, pyridine, morpholines, piperidine, 4-(N, N-dimethylin) pyridine and inorganic base as catalysts. Part of compounds of the invention has good inhibition for gibberellic disease, wilt disease and rot disease on vegetables, fruits and chinese herbal medicine. When the administer drug concentration is 50 mug/ml, the inhibition ratio for pepper wilt and apple rot can reach 52. 28+-1. 46and 56. 09+-1. 43respectively.

Description

technical field [0001] The invention relates to 2-substituted sulfinyl-5-(3,4,5-trialkoxyphenyl)-1,3,4-oxadiazole derivatives with antibacterial effect and a preparation method thereof. Background technique [0002] 1,3,4-Oxadiazole derivatives have a variety of biological activities, such as insecticidal, bactericidal, anti-cancer, anti-inflammatory and so on. As early as 1969, the former French company Rhône-Planck developed the world's first pesticide containing 1,3,4-oxadiazole ring - oxadiazon. In 1978, Japan's Sumitomo Corporation launched the insecticide chlorpyramidone. Since then, this type of compound has attracted more and more attention, and has become the research and development target of many scholars. [0003] Gallic acid or pyrogallic acid is a class of fine chemicals produced from the natural products of Tara or gallnut. Using gallic acid or pyrogallic acid as raw materials, some of the isoflavone derivatives synthesized have been used as anticancer, Ant...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D271/113C07D413/12A01N43/824A01P3/00
Inventor 杨松宋宝安罗小琼陈才俊胡佳禹刘芳
Owner GUIZHOU UNIV
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