4(3H)-quinazolinone-containing 1,4-pentadiene-3-ketoxime ether derivatives and preparation method thereof

A technology of quinazolinone and pentadiene, which is applied in the application field of anti-plant virus, can solve the problems such as poor control effect of anti-viral active compounds, and achieve the effect of outstanding activity

Active Publication Date: 2017-05-31
GUIZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] The technical problem to be solved in the present invention is: provide a kind of pentadiene ketone oxime ether compound containing 4(3H)-quinazolone in the structure and preparation method thereof, to solve the antiviral active compound in the prior art in the prevention and treatment of Technical Problems of Poor Control Effects on Plant Viruses

Method used

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  • 4(3H)-quinazolinone-containing 1,4-pentadiene-3-ketoxime ether derivatives and preparation method thereof
  • 4(3H)-quinazolinone-containing 1,4-pentadiene-3-ketoxime ether derivatives and preparation method thereof
  • 4(3H)-quinazolinone-containing 1,4-pentadiene-3-ketoxime ether derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] (3-(4(3H)-quinazolinone))methyl-1-(4-(3-chlorobenzyloxy)phenyl)-5-(2-pyridyl)-1,4-pentanedi The synthesis of en-3-ketone oxime ether (compound number is I 1 ), including the following steps:

[0059] (1) Synthesis of 4-(hydroxyphenyl)-3-buten-2-one:

[0060] Add 4-hydroxybenzaldehyde (6.1g, 50mmol) into 60mL of acetone, stir for about 15min, ice-bath the reaction system for about 30min, add about 100mL of 5% NaOH solution to the system, and wait until the dropwise addition is complete Finally, remove the ice bath and stir at room temperature for about 24 hours. After the reaction is over, transfer the system to a 500mL beaker and add an appropriate amount of ice water, and then use 5% dilute hydrochloric acid solution to adjust the pH of the system to about 5-6. After a large amount of yellow solids precipitate, extract the solids, and finally use ethanol to / water system recrystallized to obtain 5.30 g of yellow solid (theoretical mass: 8.10 g), with a yield of 65%....

Embodiment 2

[0074] (3-(4(3H)-quinazolinone))methyl-1-(4-(2-chlorobenzyloxy)phenyl)-5-(3-pyridyl)-1,4-pentanedi The synthesis of en-3-ketone oxime ether (compound number is I 2 ), including the following steps:

[0075] (1) Synthesis of 4-(hydroxyphenyl)-3-buten-2-one:

[0076] As in the first (1) step of Example 1.

[0077] (2) Synthesis of 1-(3-pyridyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one:

[0078] As in step (2) of Example 1, the difference is that pyridine-3-carbaldehyde is used as a raw material.

[0079] (3) Synthesis of 1-(4-(2-chlorobenzyloxy)phenyl)-5-(3-pyridyl)-1,4-pentadien-3-one:

[0080] As in step (3) of Example 1, the difference is that 1-(3-pyridyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one and o-chlorobenzyl chloride are used as raw materials .

[0081] (4) Synthesis of 1-(4-(2-chlorobenzyloxy)phenyl)-5-(3-pyridyl)-1,4-pentadien-3-one oxime:

[0082] As in step (4) of Example 1, the difference is that 1-(4-(2-chlorobenzyloxy)phenyl)-5-(3-pyridyl)-1,4-pentadien-3-...

Embodiment 3

[0090] (3-(4(3H)-quinazolinone))methyl-1-(4-(3-methylbenzyloxy)phenyl)-5-(2-pyridyl)-1,4-pentane The synthesis of diene-3-ketoxime ether (compound number is I 3 ), including the following steps:

[0091] (1) Synthesis of 4-(hydroxyphenyl)-3-buten-2-one:

[0092] As in the first (1) step of Example 1.

[0093] (2) Synthesis of 1-(2-pyridyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one:

[0094] As in embodiment 1 (2) step.

[0095] (3) Synthesis of 1-(4-(3-methylbenzyloxy)phenyl)-5-(2-pyridyl)-1,4-pentadien-3-one:

[0096] As in the (3) step of Example 1, the difference is that m-methylbenzyl chloride is used as a raw material.

[0097] (4) Synthesis of 1-(4-(3-methylbenzyloxy)phenyl)-5-(2-pyridyl)-1,4-pentadien-3-one oxime:

[0098] As in step (4) of Example 1, the difference is that 1-(4-(3-methylbenzyloxy)phenyl)-5-(2-pyridyl)-1,4-pentadiene-3- Ketones as raw materials.

[0099] (5) Synthesis of 3-(hydroxymethyl)quinazolin-4(3H)ketone:

[0100] As in step (5) of Example ...

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Abstract

The invention discloses 4(3H)-quinazolinone-containing 1,4-pentadiene-3-ketoxime ether derivatives. The 4(3H)-quinazolinone-containing 1,4-pentadiene-3-ketoxime ether derivatives are characterized in that the general formula of the derivatives is described in the description, wherein R1 is phenyl, substituted phenyl or substituted aromatic heterocyclic group; R2 is phenyl, substituted phenyl or substituted aromatic heterocyclic group; R3 is one or more hydrogen atoms, methoxy group, nitro group, methyl group, trifluoromethyl group or halogen atoms contained in the 5, 6, 7 or 8 site of 4(3H)-quinazolinone. The compounds provided by the invention have higher treatment and protection functions for cucumber mosaic virus (CMV) and tobacco mosaic virus (TMV), and shows better plant virus resisting activity, thus being used for preparing anti-plant-virus pesticides.

Description

technical field [0001] The invention relates to the technical field of chemical industry, in particular to a preparation method of pentadienone oxime ether derivatives containing 4(3H)-quinazolinone and its application in anti-plant virus. Background technique [0002] Every year, the economic losses caused by crops infected with plant viruses are as high as 600 billion US dollars. Therefore, effective control and treatment of plant virus diseases are of great significance to the development of the entire agriculture. Among many plant viruses, tobacco mosaic disease has the characteristics of high incidence and difficult control, and is listed as one of the most destructive plant viruses. However, all the plant antiviral agents that have been commercialized so far have only 30-50% therapeutic activity against plant viruses at a concentration of 500 μg / mL, and the inhibition results are obviously unsatisfactory. Therefore, how to develop new, efficient and environmentally fr...

Claims

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Application Information

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IPC IPC(8): C07D239/88C07D401/12
CPCC07D239/88C07D401/12
Inventor 薛伟王晓斌李琴陈丽娟谢艳王一会吴小琼张菊平阮祥辉羊春燕何桂芳
Owner GUIZHOU UNIV
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