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Quinazoline-containing 1,4-pentadiene-3-ketone oxime ether derivative as well as preparation method and application thereof

A technology of pentadiene and quinazoline, which is applied in the preparation of pentadiene ketone oxime ether derivatives and the application field of anti-plant virus, which can solve the problems that have not been seen before

Inactive Publication Date: 2018-01-09
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] In summary, 1,4-pentadien-3-one compounds and quinazolinone compounds have certain research value in anti-plant virus, but there are no compounds with anti-viral activity created at present. It surpasses Ningnanmycin in two aspects of protection and therapeutic activity, and there is no information about the synthesis of quinazoline-containing 1,4-pentadiene-3-ketoxime ether compounds, anti-plant virus activity and inhibitory effect. Reports on bacterial activity

Method used

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  • Quinazoline-containing 1,4-pentadiene-3-ketone oxime ether derivative as well as preparation method and application thereof
  • Quinazoline-containing 1,4-pentadiene-3-ketone oxime ether derivative as well as preparation method and application thereof
  • Quinazoline-containing 1,4-pentadiene-3-ketone oxime ether derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] (4-quinazolinyl)-1-(4-(3-methylbenzyloxy)phenyl)-5-(2-pyridyl)-1,4-pentadiene-3-ketoxime ether Synthesis (compound number is I 1 ), including the following steps:

[0048] (1) Synthesis of 4-(hydroxyphenyl)-3-buten-2-one:

[0049]Add 4-hydroxybenzaldehyde (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 remove the In an ice bath, 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 a yellow solid with a yield of 68%.

[0050] (2) Synthesis of 1-(2-pyridyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one:

[0051] Add 4-(hydroxyphenyl)-3-buten...

Embodiment 2

[0061] Synthesis of (4-chloroquinazolinyl)-1-(4-(2-chlorobenzyloxy)phenyl)-5-(2-pyridyl)-1,4-pentadiene-3-ketoxime ether (the compound number is I 2 ), including the following steps:

[0062] (1) Synthesis of 4-(hydroxyphenyl)-3-buten-2-one:

[0063] As in the first (1) step of Example 1.

[0064] (2) Synthesis of 1-(2-pyridyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one:

[0065] As in embodiment 1 (2) step.

[0066] (3) Synthesis of 1-(4-(2-chlorobenzyloxy)phenyl)-5-(2-pyridyl)-1,4-pentadien-3-one:

[0067] As in step (3) of Example 1, the difference is that 1-(2-pyridyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one and o-chlorobenzyl chloride are used as raw materials .

[0068] (4) Synthesis of 1-(4-(2-chlorobenzyloxy)phenyl)-5-(2-pyridyl)-1,4-pentadien-3-one oxime:

[0069] As in step (4) of Example 1, the difference is that 1-(4-(2-chlorobenzyloxy)phenyl)-5-(2-pyridyl)-1,4-pentadien-3-one For the raw material.

[0070] (5) Synthesis of 4-chloroquinazoline:

[0071] As i...

Embodiment 3

[0075] Synthesis of (4-chloroquinazolinyl)-1-(4-(4-chlorobenzyloxy)phenyl)-5-(2-pyridyl)-1,4-pentadiene-3-ketoxime ether (the compound number is I 3 ), including the following steps:

[0076] (1) Synthesis of 4-(hydroxyphenyl)-3-buten-2-one:

[0077] As in the first (1) step of Example 1.

[0078] (2) Synthesis of 1-(2-pyridyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one:

[0079] As in embodiment 1 (2) step.

[0080] (3) Synthesis of 1-(4-(4-chlorobenzyloxy)phenyl)-5-(2-pyridyl)-1,4-pentadien-3-one:

[0081] As in step (3) of Example 1, the difference is that 1-(2-pyridyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one and p-chlorobenzyl chloride are used as raw materials .

[0082] (4) Synthesis of 1-(4-(4-chlorobenzyloxy)phenyl)-5-(2-pyridyl)-1,4-pentadien-3-one oxime:

[0083] As in step (4) of Example 1, the difference is that 1-(4-(4-chlorobenzyloxy)phenyl)-5-(2-pyridyl)-1,4-pentadien-3-one For the raw material.

[0084] (5) Synthesis of 4-chloroquinazoline:

[0085] As i...

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Abstract

The invention discloses a quinazoline-containing 1,4-pentadiene-3-ketone oxime ether derivative. The quinazoline-containing 1,4-pentadiene-3-ketone oxime ether derivative is characterized in that thegeneral formula is shown in the description, wherein R1 is phenyl, substituted phenyl or substituted heteroaromatic ring radical; R2 is phenyl, substituted phenyl or substituted heteroaromatic ring radical; R3 is one or more of hydrogen atoms, methoxyl groups, nitryl groups, methyl groups, trifluoromethyl groups or halogen atoms at 5-, 6-, 7- or 8-position of quinazoline. The compound provided bythe invention has good treatment and protection effects on cucumber mosaic virus (CMV) and tobacco mosaic virus (TMV), has higher plant virus activity resistance, and can be applied to preparation ofpesticides for resisting plant viruses.

Description

technical field [0001] The invention relates to the technical field of chemical industry, in particular to a preparation method of quinazoline-containing pentadienone oxime ether derivatives 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 friendly p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07D239/88C07D401/12A01N43/54A01P1/00A01P3/00
CPCA01N43/54C07D239/88C07D401/12
Inventor 薛伟李琴王一会张橙李普张菊平阮祥辉吴小琼王俊
Owner GUIZHOU UNIV
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