Substituted phenyl furan-2-mercaptothiazoline ketone compound as well as preparation method thereof and application

A technology of mercaptothiazoline ketone and mercaptothiazoline, which is applied in the field of synthesis of heterocyclic compounds, and achieves the effects of simple preparation method, novel structure, and prevention of drug resistance

Active Publication Date: 2019-01-25
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] Although there are a variety of thiazole heterocyclic compounds, these compounds still have unlimited research and development space, and further research can be carried out to develop more application values ​​and prospects

Method used

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  • Substituted phenyl furan-2-mercaptothiazoline ketone compound as well as preparation method thereof and application
  • Substituted phenyl furan-2-mercaptothiazoline ketone compound as well as preparation method thereof and application
  • Substituted phenyl furan-2-mercaptothiazoline ketone compound as well as preparation method thereof and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Embodiment 1: the synthesis of compound III-1

[0067] Add 15mmol 2-mercaptothiazoline and 10mL methylene chloride in a 50mL three-necked flask equipped with a thermometer, add 10% (wt.) sodium hydroxide aqueous solution containing 15mmol sodium hydroxide at room temperature, control the rate of addition, and keep the temperature at room temperature. After this was completed, a dichloromethane solution containing 7.5 mmol of 5-(2-chlorophenyl)-2-furoyl chloride was added dropwise. Control the rate of addition so that both are added at the same time. After the dropwise addition, slowly raise the temperature to 50°C, and react at 50°C for 3-10 hours. After the reaction was completed, filter to remove the precipitate, and rotate the filtrate to remove the solvent to obtain a light yellow solid. Compound III-1 was obtained by separation on a silica gel column (eluent: petroleum ether / ethyl acetate volume ratio: 3 / 1), yield: 58% (III-1); 1 H NMR (400MHz, CDCl 3 )δ3.50(2...

Embodiment 2

[0069] Embodiment 2: the synthesis of compound III-2

[0070] The method was the same as in Example 1, except that 5-(3-fluorophenyl)-2-furoyl chloride was used instead of 5-(2-chlorophenyl)-2-furoyl chloride to obtain yellow solid III-2.

[0071] 1 H NMR (400MHz, CDCl 3 )δ3.51(2H,t,J=8.0Hz),4.51(2H,t,J=8.0Hz),6.85(1H,d,J=4.0Hz),7.21-7.92(5H,m).

[0072]

Embodiment 3

[0073] Embodiment 3: the synthesis of compound III-3

[0074] The method is the same as in Example 1, except that 5-(4-chlorophenyl)-2-furoyl chloride is used instead of 5-(2-chlorophenyl)-2-furoyl chloride to obtain yellow solid III-3.

[0075] 1 H NMR (400MHz, CDCl 3 )δ3.51(2H,t,J=6.0Hz),4.51(2H,t,J=6.0Hz),6.77(1H,s),7.35(1H,s),7.39(2H,d,J=8.0 Hz),7.67(2H,d,J=8.0Hz).

[0076]

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PUM

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Abstract

The invention discloses a substituted phenyl furan-2-mercaptothiazoline ketone compound as well as a preparation method and application thereof. The structure of the compound is as shown in a structural formula (III). The invention also discloses a preparation method and application of the compound. The substituted phenyl furan-2-mercaptothiazoline ketone compound provided by the invention is novel in structure, simple in preparation method and high in yield; the compound has an obvious inhibiting effect on an xanthomonas oryzae pv III type secretory system (T3SS), and can be taken as a xanthomonas oryzae pv T3SS activity inhibitor, especially a compound III-7, which does not affect growth of xanthomonas oryzae pv while pathogenicity of the xanthomonas oryzae pv is reduced, so that pathogenic bacteria can be prevented from generating drug resistance, and the effects of preventing and/or controlling the xanthomonas oryzae pv also can be achieved. (The formula is as shown in specification.).

Description

technical field [0001] The present invention belongs to the field of synthesis of heterocyclic compounds, in particular to compounds containing phenylfuran ring mercaptothiazolinones, more specifically, to a class of substituted phenylfuran-2-mercaptothiazolinones and their preparation methods and applications . Background technique [0002] In recent years, with more and more reports of heterocyclic compounds with biological activity and novel structures, the design and synthesis of various heterocyclic compounds has become a research hotspot, among which the research on thiazole heterocyclic compounds has become increasingly active. A series of application results and commercial products have been obtained. Since different functional groups can be introduced into the 2, 3, 4, and 5 positions of the thiazole ring, there are many kinds of thiazole heterocyclic compounds, many of which have good biological activity. [0003] (1) Agricultural fungicides [0004] Thifluzamid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/06A01N43/78A01P1/00
CPCA01N43/78C07D417/06
Inventor 崔紫宁陶辉田浩姜珊向绪稳
Owner SOUTH CHINA AGRI UNIV
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