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Myricetin derivative containing quinoxaline and preparation method and application thereof

A kind of derivative, the technology of quinoxaline, applied in the field of myricetin derivatives, to achieve the effect of good anti-plant virus

Active Publication Date: 2019-01-18
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no report on the introduction of quinoxaline active groups into myricetin to synthesize quinoxaline-containing myricetin derivatives and to test their agricultural activity.

Method used

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  • Myricetin derivative containing quinoxaline and preparation method and application thereof
  • Myricetin derivative containing quinoxaline and preparation method and application thereof
  • Myricetin derivative containing quinoxaline and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 5,7-Dimethoxy-3-(3-(quinoxalin-2-yloxy)propoxy)-2-(3,4,5-trimethoxyphenyl)-4H-chromene -4-ketone (target compound A 1 ) preparation method, comprising the following steps:

[0026] (1) Preparation of 3-hydroxy-3',4',5',5,7-pentamethoxymyricetin

[0027] In a 250mL round bottom flask, add 4.64g myricetin (10mmol), 22.09g K 2 CO 3 (16mmol) and 120mL DMF, stirred at room temperature for 0.5~1h, slowly added 7.50mL iodomethane (120mmol) dropwise, stirred at room temperature for 48h, TLC followed the reaction (methanol:ethyl acetate=1:4, V / V). After stopping the reaction, filter the precipitate, wash the filter residue with dichloromethane, combine the filtrates, dilute with 100mL water, or extract three times with dichloromethane, combine the organic layers, concentrate under reduced pressure, and then dissolve the concentrate in 30mL absolute ethanol , heated to reflux, after the solution was clarified, 16mL of concentrated hydrochloric acid was added under reflux, and...

Embodiment 2

[0033] 3-(3-(3-Hydroxyquinoxalin-2-yl)oxy)propoxy-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H -Chromene-4-one (target compound A 2 ) preparation method, comprising the following steps:

[0034] (1) Preparation of 3-hydroxy-3',4',5',5,7-pentamethoxymyricetin

[0035] As in the first (1) step of Example 1.

[0036] (2) Preparation of 3(3-bromopropoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one

[0037] As in embodiment 1 (2) step.

[0038] (3) 3-(3-(3-hydroxyquinoxalin-2-yl)oxy)propoxy-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl )-4H-chromen-4-one preparation

[0039] As in step (3) of Example 1, the difference is that 2,3-dihydroxyquinoxaline is used as a raw material. Yield: 52%.

Embodiment 3

[0041] 5,7-Dimethoxy-3-(3-((3-methylquinoxalin-2-yl)oxy)propoxy)-2-(3,4,5-trimethoxyphenyl )-4H-chromen-4-one (target compound A 3 ) preparation method, comprising the following steps:

[0042] (1) Preparation of 3-hydroxy-3',4',5',5,7-pentamethoxymyricetin

[0043] As in the first (1) step of Example 1.

[0044] (2) Preparation of 3(3-bromopropoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one

[0045] As in embodiment 1 (2) step.

[0046] (3) 5,7-dimethoxy-3-(3-((3-methylquinoxalin-2-yl)oxy)propoxy)-2-(3,4,5-trimethoxy Preparation of phenyl)-4H-chromen-4-one

[0047] As in step (3) of Example 1, the difference is that 2-hydroxyl-3-methylquinoxaline is used as a raw material. Yield: 63%.

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PUM

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Abstract

The invention discloses a myricetin derivative containing quinoxaline and a preparation method and application thereof. The myricetin derivative has a structural formula (A), wherein R is positioned at the 3rd, 5th, 6th, 7th or 8th site of the quinoxaline structure and contains more than one hydrogen atom, hydroxyl, C1-6 alkyl, C1-6 alkoxy and halogen atom; n is the number of carbons in the carbonchain, such as 3, 4, 5 and 6. The myricetin derivative has good preventing and controlling effects on tobacco mosaic viruses, xanthomonas citri and xanthomonas oryzae. The structural formula (A) is shown in the attached figure.

Description

technical field [0001] The invention relates to the technical field of chemical engineering, in particular to a quinoxaline-containing myricetin derivative. At the same time, it also relates to the preparation method of the quinoxaline-containing myricetin derivative and the application of the quinoxaline-containing myricetin derivative in anti-plant virus and anti-plant pathogenic bacteria. Background technique [0002] Myricetin (3', 4', 5', 3, 5, 7-hexahydroxyflavonol, Myricetin (Myr)), belongs to polyhydric flavonol compounds, synonymous myricetin, myricetin, myricetin, It is an important natural product that widely exists in a variety of plants, such as: daily edible fruits, vegetables and beverages, and has rich sources. According to modern pharmacological activity studies, myricetin has various pharmacological activities such as antibacterial, antiviral, antiallergic, anti-inflammatory, antioxidative, hypoglycemic, and neuroprotective. [0003] In 2008, Qi et al. (Q...

Claims

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Application Information

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IPC IPC(8): C07D405/12A01N43/60A01P1/00A01P3/00
CPCA01N43/60C07D405/12
Inventor 薛伟李普夏榕娇陈英郭涛汤旭蒋仕春张敏李向阳贺鸣
Owner GUIZHOU UNIV
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