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Triazole Schiff base Myricetin derivative containing thioether, preparation method and application thereof

A technology of triazole schiff base and derivatives is applied in the field of preparation of triazole schiff alkaloid myricetin derivatives, can solve problems such as lack of unwinding activity, and achieve the effects of good resistance to plant viruses and excellent inhibition of plant pathogens

Active Publication Date: 2019-03-08
GUIZHOU UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] 2012, Yu et al. (Yu, M.S.; Lee, J.; Lee, J.M.; Kim, Y.; Chin, Y.W.; Jee, J.G.; Keum, Y.S.; Jeong, Y.J. Communications in Bioorganic and Medicinal Chemistry, 2012, 22(12):4049-4054.) studied the inhibitory effect of myricetin on the SARS virus in vitro by performing a double-stranded DNA unwinding assay using fluorescence resonance energy transfer (FRET) or using a colorimetric-based hydrolysis assay. It was found that myricetin potentially inhibited the SARS virus helicase protein, affected the activity of ATPase, but had no unwinding activity, and myricetin did not show cytotoxicity to normal breast epithelial MCF10A cells
However, there is no report on introducing the active group of triazole Schiff base containing thioether into myricetin to synthesize myricetin derivatives containing triazole Schiff base containing thioether and to test its agricultural activity.

Method used

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  • Triazole Schiff base Myricetin derivative containing thioether, preparation method and application thereof
  • Triazole Schiff base Myricetin derivative containing thioether, preparation method and application thereof
  • Triazole Schiff base Myricetin derivative containing thioether, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 3-(3-((5-Methyl-4-((benzylidene)amino)-4H-1,2,4-triazol-3-yl)thio)propoxy)-5,7- Dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-benzopyran-4-one (target compound A 1 ) preparation method, comprising the following steps:

[0033] (1) Preparation of hydrazinothiohydrazide (intermediate 1):

[0034]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 CS was added dropwise within 1 h 2 , and then the mixed solution was refluxed at 90° C. for 1 h, cooled to crystallize, suction filtered, and recrystallized in water to obtain colorless needle-like crystals (intermediate 1), yield: 82%.

[0035] (2) Preparation of 4-amino-5-methyl-4H-1,2-4-triazole-3-mercapto (intermediate 2):

[0036] Take 3.18g (0.03mol) of hydrazinothiohydrazide (intermediate 1) in a flask, ad...

Embodiment 2

[0046] 3-(3-((5-methyl-4-((4-methylbenzylidene)amino)-4H-1,2,4-triazol-3-yl)thio)propoxy)- 5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one (target compound A 2 ) preparation method, comprising the following steps:

[0047] (1) Preparation of hydrazinothiohydrazide (intermediate 1):

[0048] As in the first (1) step of Example 1.

[0049] (2) Preparation of 4-amino-5-methyl-4H-1,2,4-triazole-3-mercapto (intermediate 2):

[0050] As in embodiment 1 (2) step.

[0051] (3) Preparation of 5-methyl-4-((4-methylbenzylidene)amino)-4H-1,2,4-triazole-3-thiol:

[0052] As in the (3) step of embodiment 1, the difference is that p-tolualdehyde is used as raw material.

[0053] (4) Preparation of 3-hydroxy-3',4',5',5,7-pentamethoxymyricetin:

[0054] As embodiment 1 (4) step.

[0055] (5) 3-(3-bromopropoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one (intermediate 5) Preparation:

[0056] As in step (5) of Example 1.

[0057] (6) 3-(3-((5-methyl-4-((4-methy...

Embodiment 3

[0060] 3-(3-((5-methyl-4-((3-methylbenzylidene)amino)-4H-1,2,4-triazol-3-yl)thio)propoxy)- 5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one (target compound A 3 ) preparation method, comprising the following steps:

[0061] (1) Preparation of hydrazinothiohydrazide (intermediate 1):

[0062] As in the first (1) step of Example 1.

[0063] (2) Preparation of 4-amino-5-methyl-4H-1,2,4-triazole-3-mercapto (intermediate 2):

[0064] As in embodiment 1 (2) step.

[0065] (3) Preparation of 5-methyl-4-((3-methylbenzylidene)amino)-4H-1,2,4-triazole-3-thiol

[0066] As in the (3) step of embodiment 1, the difference is that taking m-tolualdehyde as raw material.

[0067] (4) Preparation of 3-hydroxy-3',4',5',5,7-pentamethoxymyricetin

[0068] As embodiment 1 (4) step.

[0069] (5) 3-(3-bromopropoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one (intermediate 5) Preparation:

[0070] As in step (5) of Example 1.

[0071] (6) 3-(3-((5-methyl-4-((3-methylbe...

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Abstract

The invention discloses a triazole Schiff base Myricetin derivative containing thioether, a preparation method and application thereof. The structural general formula of the derivative is shown as [A], wherein R is phenyl, substituted phenyl or aromatic heterocyclic base; and n is the number of carbon in a carbon chain, which is 3, 4 and 5 respectively. The triazole Schiff base Myricetin derivative has preferable control effect for tobacco mosaic virus, citrus canker bacteria and rice bacterial blight bacteria.

Description

technical field [0001] The present invention relates to the technical field of chemical engineering, in particular to a thioether-containing triazole Schiff base myricetin derivative, and also to a preparation method of the thioether-containing triazole Schiff base myricetin derivative, and the Application of thioether-containing triazole Schiff base myricetin derivatives in inhibiting plant pathogens. Background technique [0002] Myricetin (3',4',5',3,5,7-hexahydroxyflavonol, Myricetin (Myr)), synonymous myricetin, myricetin, is a polyhydroxy Flavonoids, chemical formula C 15 h 10 o 8 , relative molecular weight 318.24, yellow needle-like or granular crystal, melting point 324-326 ° C, soluble in methanol, ethanol, acetone, insoluble in chloroform, petroleum ether. It exists in plants such as Fagaceae, leguminosae, primulaceae, vitaceae, and compositae. According to modern pharmacological activity studies, myricetin has various pharmacological activities such as antib...

Claims

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Application Information

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IPC IPC(8): C07D405/12C07D409/14A01N43/653A01P1/00
CPCA01N43/653C07D405/12C07D409/14
Inventor 薛伟李普陈英张敏金梅梅唐显富王岚贺鸣
Owner GUIZHOU UNIV
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