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Myricetin derivative containing amide-oxadiazole and preparation method and application of myricetin derivative

A technology of oxadiazole and derivatives, applied in the field of preparation of myricetin derivatives, can solve the problem of less applied research

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

AI Technical Summary

Problems solved by technology

[0009] In summary, myricetin has good antiviral activity and antibacterial activity in medical research, but less research has been done on the application of p

Method used

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  • Myricetin derivative containing amide-oxadiazole and preparation method and application of myricetin derivative
  • Myricetin derivative containing amide-oxadiazole and preparation method and application of myricetin derivative
  • Myricetin derivative containing amide-oxadiazole and preparation method and application of myricetin derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 2-((5,7-dimethoxy-4-one-2-(3,4,5-trimethoxyphenyl)-4H-chromen-3-yl)oxy-N-(5- The preparation method of phenyl-1,3,4-oxadiazol-2-yl)acetamide (target compound 4a), comprises the following steps:

[0029] (1) Preparation of 2-amino-5-phenyl-1,3,4-oxadiazole

[0030] Add semicarbazide hydrochloride (9.42mmol) and sodium acetate (9.42mmol) to a 100mL round-bottomed flask, dissolve them with 20mL of secondary water, then slowly add 20mL of methanol containing benzaldehyde (9.42mmol) dropwise, at room temperature Stir for 20 minutes. Spin the solvent to dryness, add 40mL 1,4-dioxane, potassium carbonate (28.37mmol), iodine element (10.37mmol), heat at 80-85°C for 4-6 hours, track the reaction by TLC until no more Variety. The reactant was poured into 25% aqueous sodium thiosulfate solution, extracted with a mixed solvent of dichloromethane:methanol=10:1, dried with anhydrous sodium sulfate, spin-dried, N,N-dimethylformamide and Recrystallization from dichloromethane gave ...

Embodiment 2

[0038] 2-((5,7-dimethoxy-4-one-2-(3,4,5-trimethoxyphenyl)-4H-chromen-3-yl)oxy-N-((5 -(4-methyl)phenyl)-1,3,4-oxadiazol-2-yl)acetamide (target compound 4b) preparation method, comprising the following steps:

[0039] (1) Preparation of 2-amino-5-((4-methyl)-phenyl)-1,3,4-oxadiazole

[0040] As in the (1) step of embodiment 1, the difference is that p-tolualdehyde is used as a raw material.

[0041] (2) Preparation of 2-chloro-N-((5-(4-methyl)phenyl)-1,3,4-oxadiazole)-acetamide

[0042] As in step (2) of Example 1, the difference is that 2-amino-5-((4-methyl)-phenyl)-1,3,4-oxadiazole is used as the raw material.

[0043] (3) Preparation of 3-hydroxy-3',4',5',5,7-pentamethoxymyricetin

[0044] As in embodiment 1 (3) step.

[0045] (4) 2-((5,7-dimethoxy-4-one-2-(3,4,5-trimethoxyphenyl)-4H-chromen-3-yl)oxy-N- Preparation of ((5-(4-methyl)phenyl)-1,3,4-oxadiazol-2-yl)acetamide.

[0046] As in step (5) of Example 1, the difference is that 2-chloro-N-((5-(4-methyl)phenyl)-1,3,4-...

Embodiment 3

[0048] 2-((5,7-dimethoxy-4-one-2-(3,4,5-trimethoxyphenyl)-4H-chromen-3-yl)oxy-N-((5 -(4-methoxy)phenyl)-1,3,4-oxadiazol-2-yl)acetamide (target compound 4c) preparation method, comprising the following steps:

[0049] (1) Preparation of 2-amino-5-((4-methoxy)-phenyl)-1,3,4-oxadiazole

[0050] As in the first (1) step of embodiment 1, the difference is that p-methoxybenzaldehyde is used as a raw material.

[0051] (2) Preparation of 2-chloro-N-((5-(4-methoxy)phenyl)-1,3,4-oxadiazole)-acetamide

[0052] As in step (2) of Example 1, the difference is that 2-amino-5-((4-methoxy)-phenyl)-1,3,4-oxadiazole is used as the raw material.

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

[0054] As in embodiment 1 (3) step.

[0055] (4) 2-((5,7-dimethoxy-4-one-2-(3,4,5-trimethoxyphenyl)-4H-chromen-3-yl)oxy-N- Preparation of ((5-(4-methoxy)phenyl)-1,3,4-oxadiazol-2-yl)acetamide.

[0056] As in step (4) of Example 1, the difference is that 2-chloro-N-((5-(4-met...

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Abstract

The invention discloses a myricetin derivative containing amide-oxadiazole and a preparation method and application of the myricetin derivative. General formula (A) is as shown in specification, wherein R is alkyl consisting of 1-6 carbon atoms, alkoxy consisting of 1-6 carbon atoms, halogen atoms and nitryl. According to substituted phenyl, one or two alkyls consisting of 1-6 carbon atoms, alkoxyconsisting of 1-6 carbon atoms, halogen and nitryl are arranged at an ortho-position, a meta-position and a para-position of a benzene ring. The myricetin derivative resists tobacco mosaic viruses, xanthomonas citri and xanthomonas oryzae pv. oryzae.

Description

technical field [0001] The present invention relates to the field of chemical technology, in particular to a myricetin derivative containing amide oxadiazole, a method for preparing the amide oxadiazole-containing myricetin derivative, and the amide oxadiazole-containing derivative Application of myricetin derivatives in anti-plant virus and inhibition of plant pathogenic bacteria. Background technique [0002] Myricetin, also known as myricetin, myricetin, myricetin, belongs to flavonol compounds, widely exists in a variety of plants, and its sources are abundant. In 2000, He Guixia et al. (He Guixia, Pei Gang, Yao, et al. Chinese Journal of Ethnic Medicine, 2000, 6, 40-41.) isolated from the stem of vine tea. Pharmacological studies have shown that myricetin has biological activities such as antitumor, antibacterial, antiviral, antioxidative and anti-inflammatory, and has certain research and application value. But most of them are limited to medical research, and there ...

Claims

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Application Information

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IPC IPC(8): C07D413/12A01N43/82A01P1/00A01P3/00
CPCA01N43/82C07D413/12
Inventor 薛伟张橙陈丽娟陈英蒋仕春郭涛夏榕娇汤旭李向阳贺鸣
Owner GUIZHOU UNIV
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