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1, 4-pentadiene-3-one derivative containing thioether triazole, preparation method and application

A technology of pentadiene and its derivatives, applied in the field of antiviral and antibacterial activities, and the preparation of 1,4-pentadien-3-one derivatives, to achieve excellent activity and good activity

Active Publication Date: 2019-05-07
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, there are no related reports on introducing thioether-containing triazoles into the pentadiene structure and testing the antibacterial and antiviral activities

Method used

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  • 1, 4-pentadiene-3-one derivative containing thioether triazole, preparation method and application
  • 1, 4-pentadiene-3-one derivative containing thioether triazole, preparation method and application
  • 1, 4-pentadiene-3-one derivative containing thioether triazole, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] 1-(4-(2-((4-Amino-5-methyl-4H-1,2,4-triazol-3-yl)thio)ethoxy)phenyl)-5-(4- The preparation method of nitrophenyl)-1,4-pentadien-3-one (target compound A1), comprises the following steps:

[0032] (1) Preparation of hydrazinothiohydrazide (intermediate 1):

[0033] Add 20mL of 85% hydrazine hydrate and 60mL of water to a three-neck flask equipped with a thermometer, dropping funnel and condenser (the upper port is connected with a tail gas outlet pipe), and control the temperature at about 50°C. Under electromagnetic stirring, 6 mL of CS2 was added dropwise within 1 h, and then the mixed solution was refluxed at 90° C. for 1 h, cooled and crystallized, filtered with suction, and recrystallized in water to obtain colorless needle-shaped crystals (intermediate 1), yield: 82% .

[0034] (2) Preparation of 4-amino-5-methyl-4H-1,2,4-triazole-3-mercapto (intermediate 2):

[0035] Take 3.18g (0.03mol) of hydrazinothiohydrazide (intermediate 1) in a flask, add 10mL of glacial...

Embodiment 2

[0043] (4-(2-((4-amino-5-methyl-4H-1,2,4-triazol-3-yl)thio)ethoxy)phenyl)-5-(4-chlorobenzene Base)-1,4-pentadien-3-ketone (target compound A2) preparation method, comprises the following steps:

[0044] (1) Preparation of hydrazinothiohydrazide (intermediate 1):

[0045] As in the first (1) step of Example 1.

[0046] (2) Preparation of 4-amino-5-methyl-4H-1,2,4-triazole-3-mercapto (intermediate 2):

[0047] As in embodiment 1 (2) step.

[0048] (3) Preparation of 4-(hydroxyphenyl)-3-buten-2-one (intermediate 3):

[0049] As in embodiment 1 (3) step.

[0050] (4) Preparation of 1-(4-chloro)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one:

[0051] As in step (4) of Example 1, the difference is that R is 4-chlorobenzaldehyde.

[0052] (5) Preparation of 1-(4-(2-bromoethoxy)phenyl)-5-(4-chlorophenyl)-1,4-pentadien-3-one:

[0053] As in step (5) of Example 1, the difference is that R is 4-chlorobenzaldehyde.

[0054] (6) 1-(4-(2-((4-amino-5-methyl-4H-1,2,4-triazol-3-yl)thio)ethox...

Embodiment 3

[0057] 1-(4-(2-((4-Amino-5-methyl-4H-1,2,4-triazol-3-yl)thio)ethoxy)phenyl)-5-(4- Fluorophenyl)-1,4-pentadien-3-one (target compound A3) preparation method, comprises the following steps:

[0058] (1) Preparation of hydrazinothiohydrazide (intermediate 1):

[0059] As in the first (1) step of Example 1.

[0060] (2) Preparation of 4-amino-5-methyl-4H-1,2,4-triazole-3-mercapto (intermediate 2):

[0061] As in embodiment 1 (2) step.

[0062] (3) Preparation of 4-(hydroxyphenyl)-3-buten-2-one (intermediate 3):

[0063] As in embodiment 1 (3) step.

[0064] (4) Preparation of 1-(4-fluoro)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one:

[0065] As in step (4) of Example 1, the difference is that R is 4-fluorobenzaldehyde.

[0066] (5) Preparation of 1-(4-(2-bromoethoxy)phenyl)-5-(4-fluorophenyl)-1,4-pentadien-3-one:

[0067] As in step (5) of Example 1, the difference is that R is 4-fluorobenzaldehyde.

[0068] (6) 1-(4-(2-((4-amino-5-methyl-4H-1,2,4-triazol-3-yl)thio)ethoxy)phen...

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Abstract

The invention discloses a 1, 4-pentadiene-3-one derivative containing thioether triazole, a preparation method and application. The structural general formula is shown as the specification, wherein Xis 2-O or 4-O, R is phenyl, substituted phenyl, heterocyclyl or 4-methylthiazole. The 1, 4-pentadiene-3-one derivative containing thioether triazole provided by the invention has good control effect on tobacco mosaic virus, ralstonia solanacearum and Xanthomonas oryzae pv. oryzae.

Description

technical field [0001] The present invention relates to the field of chemical technology, in particular to a 1,4-pentadien-3-one derivative containing thioethertriazole, and also to the 1,4-pentadiene derivative containing thioethertriazole A preparation method of en-3-one derivatives, and the application of the 1,4-pentadien-3-one derivatives containing thioethertriazole in antiviral and antibacterial activities. Background technique [0002] Natural active molecules and their derivatives have the characteristics of unique structure, novel mode of action, low toxicity to humans and animals, and environmental friendliness, which play a decisive role in the discovery of pesticide lead compounds. Curcumin, a polyphenolic compound derived from turmeric, is widely used as a spice, food preservative, monosodium glutamate, and dye. 1,4-pentadienone compound, as an important curcumin derivative, has broad-spectrum biological activities such as insecticidal, antibacterial, anti-pla...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/12C07D405/12A01N43/653A01P1/00
Inventor 薛伟陈英李普郭涛夏榕娇陈梅蒋仕春贺军苏时军王俊
Owner GUIZHOU UNIV
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