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Heterocyclic 1,4-pentadiene-3-ketoxime compound as well as preparation method and application thereof

A compound and pentadiene technology, applied in the field of 1-aryl-5-heterocyclyl-1,4-pentadien-3-one oxime ether compounds, can solve problems such as uninvolved

Inactive Publication Date: 2014-07-16
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In previous studies, Song Baoan et al. (Song Baoan, Wu Jian, Xue Wei, Chen Pengli, Yang Song, Zeng Song, Hu Deyu, Wang Zhenchao, Xu Weiming. 1,5-disubstituted aryl-1,4-pentadiene- 3-ketoxime ether compound and its preparation method and application of insecticidal activity [P]. CN: ZL201010272708.4, 2012-06-27:) A series of 1,5-disubstituted aryl groups containing oxime ether structure synthesized -1,4-pentadien-3-one compounds have certain insecticidal activity, but not related to the activity of 1-phenyl-5-heterocyclyl-1,4-pentadien-3-ketoxime ether antiviral activity

Method used

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  • Heterocyclic 1,4-pentadiene-3-ketoxime compound as well as preparation method and application thereof
  • Heterocyclic 1,4-pentadiene-3-ketoxime compound as well as preparation method and application thereof
  • Heterocyclic 1,4-pentadiene-3-ketoxime compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Example 1, 2-chloro-benzyl-1-[2-(3-fluorobenzyloxy)phenyl]-5-(2-thiophene)-1,4-pentadiene-3-ketoxime ether ( Compound A):

[0071] (1) Synthesis of 4-(2-hydroxyphenyl)-3-buten-2-one

[0072] Add 7.33 g (60 mmol) of o-hydroxybenzaldehyde (60 mmol) and 60 mL of acetone to a 500 mL three-necked flask, and stir until dissolved; slowly add about 5% sodium hydroxide solution 100 mL (132 mmol sodium hydroxide); stirring at room temperature, TLC tracking reaction, volume ratio, petroleum ether: ethyl acetate=2:1, after 10 h of reaction, dilute hydrochloric acid was added dropwise until the color of the solution did not change (pH was about 5), and there was yellow The solid precipitated out, stood overnight, filtered with suction, and dried naturally to obtain a yellow solid. Yield: 89%; Melting point: 139-141 °C.

[0073] (2) Preparation of 1-(2-hydroxyphenyl)-5-(2-thiophene)-1,4-pentadien-3-one

[0074] Add 3.57 g of 4-o-hydroxyphenyl-3-buten-2-one (22 mmol), 2.24 g of 2-...

Embodiment 2

[0081] Example two, 4-nitro-benzyl-1-[2-(benzyloxy)phenyl]-5-(2-thiophene)-1,4-pentadiene-3-ketoxime ether (compound D ):

[0082] (1) Synthesis of 4-(2-hydroxyphenyl)-3-buten-2-one

[0083] Synthesize as in Example 1 (1) method and conditions.

[0084] (2) Preparation of 1-(2-hydroxyphenyl)-5-(2-thiophene)-1,4-pentadien-3-one

[0085] Synthesize as in Example 1 (2) method and conditions.

[0086] (3) Preparation of 1-[2-(benzyloxy)phenyl]-5-(2-thiophene)-1,4-pentadien-3-one

[0087] Add 1.28 g 1-o-hydroxyphenyl-5-(2-thiophene)-1,4-pentadien-3-one (5 mmol), 1.04 g K 2 CO 3 (7.5 mmol), 0.25 g KI (1.50 mmol), 20 mL of acetone, stirred; dropwise added 5 mL of acetone containing 0.76 g benzyl chloride (6.00 mmol), heated to reflux; TLC tracking reaction, volume ratio, petroleum ether:ethyl acetate Ester = 3:1, 5 h after the reaction, cooled to room temperature; filtered, the filtrate was rotary evaporated to remove acetone, and recrystallized from ethanol to obtain yellow ne...

Embodiment 3

[0092] Example three, 4-nitro-benzyl-1-[4-(benzyloxy)phenyl]-5-(2-furan)-1,4-pentadiene-3-ketoxime ether (compound I ):

[0093] (1) Synthesis of 4-(4-hydroxyphenyl)-3-buten-2-one

[0094] Add 7.33 g (60 mmol) of 4-hydroxybenzaldehyde and 60 mL of acetone to a 500 mL three-necked flask, and stir until dissolved; slowly add about 5% sodium hydroxide solution 110 mL (150 mmol sodium hydroxide, 110 mL water); stirring at room temperature, TLC tracking reaction, volume ratio, petroleum ether: ethyl acetate = 2:1, after 16 h of reaction, dilute hydrochloric acid was added dropwise until the color of the solution did not change (pH approx. 5), a yellow solid was precipitated, left to stand overnight, filtered with suction, and dried naturally to obtain a yellow powder. Yield: 80%; Melting point: 96-98 °C.

[0095] (2) Preparation of 1-(4-hydroxyphenyl)-5-(2-furan)-1,4-pentadien-3-one

[0096] Take 3.57 g 4-(4-hydroxyphenyl)-3-buten-2-one (22 mmol), 1.92 g 2-furaldehyde (20 mmol)...

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Abstract

The invention discloses a heterocyclic 1,4-pentadiene-3-ketoxime compound 1 as well as a preparation method and application thereof. X in a structural formula 1 is heteroatom O or S, R[1]O can be at the ortho-position and the para-position, and R1 and R2 are one-substituted or multi-substituted aryl and substituted heterocyclic group respectively and can be substituted with one or more groups. A series of heterocyclic 1,4-pentadiene-3-ketoxime compounds are prepared by introducing furan, thiophene and oxime ether active groups on the basis of curcumin derivatives, namely 1,4-pentadiene-3-ketone. A bioactivity test shows that the compounds have the effect of controlling crop pests and especially have a certain control effect on plutella xylostella and aphids; meanwhile, the compounds have a relatively good inhibition effect on tobacco mosaic viruses (TMV).

Description

technical field [0001] The invention relates to 1-aryl-5-heterocyclyl-1,4-pentadien-3-ketoxime ether compounds with insecticidal and antiviral activities and a preparation method thereof. Background technique [0002] Curcumin has various biological activities such as insecticidal, antibacterial, antiviral, anti-inflammatory, anti-oxidant, anti-cancer, etc. Its derivatives 1,4-pentadien-3-one compounds have a wide range of biological activities like curcumin. But it has better stability and less toxic side effects. Therefore, it is expected to obtain more active 1,4-pentadien-3-one compounds by modifying the structure of curcumin as the lead compound, which provides theoretical support for the design and synthesis of green biomimetic pesticides. [0003] The following mainly describes the research progress of curcumin derivatives and their analogues 1,4-pentadien-3-ones in terms of insecticidal, antiviral, antibacterial and other biological activities. [0004] In terms of...

Claims

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Application Information

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IPC IPC(8): C07D333/22C07D307/52C07D405/12C07D409/12A01N43/10A01N43/08A01N43/40A01P1/00A01P7/04
CPCC07D333/22A01N43/08A01N43/10A01N43/40C07D307/52C07D405/12C07D409/12
Inventor 薛伟陈玉张贤王忠波朱雪松柳敏夏丽娟龚华玉赵洪菊
Owner GUIZHOU UNIV
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