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Preparation method and application for novel chalcone derivative containing quinazoline thioether

A kind of technology of oxazoline sulfide and quinazoline, applied in the field of novel chalcone derivatives containing quinazoline sulfide

Active Publication Date: 2015-05-06
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0020] As can be seen from the background technology, chalcones, quinazolines and thioether compounds all have good biological activities against plant viruses, etc., but no one has synthesized them yet.

Method used

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  • Preparation method and application for novel chalcone derivative containing quinazoline thioether
  • Preparation method and application for novel chalcone derivative containing quinazoline thioether
  • Preparation method and application for novel chalcone derivative containing quinazoline thioether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment one: (E)-3-(2-methoxyphenyl)-1-(4-(2-(quinazolin-4-ylthio)ethoxy)phenyl)prop-2-ene-1- Ketone (compound number is M 1 )Synthesis:

[0054] (1) Synthesis of intermediate 4-chloroquinazoline

[0055]Add 11.5 g (83.83 mmol) of anthranilic acid and 15.1 g (335.41 mmol) of formamide into a 100 mL round bottom flask, mix and heat to 135~145 °C, and react for 5 h. After the reaction, add 100 mL of water and cool to Add a large amount of water at 60°C, stir for 30 min, cool to room temperature, and filter with suction to obtain a light brown solid, which is recrystallized in absolute ethanol to obtain a white flocculent solid, which is quinazolin-4-one; Add quinazolin-4-one (36.32mmol), thionyl chloride (37 mL), 1,2-dichloroethane (17 mL) and DMF (1 mL) into a mL round bottom flask, reflux for 4.5 h, After the reaction is complete, evaporate most of the solvent, cool to room temperature, add 30 mL of chloroform to the residue and pour it into water together, and ...

Embodiment 2

[0064] Embodiment two: (E)-1-(4-(2-(quinazolin-4-ylthio)ethoxy)phenyl)-3-(4-(trifluoromethyl)phenyl)prop-2-ene -1-ketone (the compound number is M 2 )Synthesis:

[0065] (1) Synthesis of intermediate 4-chloroquinazoline: synthetic steps and process conditions are the same as embodiment one (1);

[0066] (2) Synthesis of intermediate 4-mercaptoquinazoline: synthetic steps and process conditions are the same as embodiment one (2);

[0067] (3) Synthesis of intermediate (E)-1-(4-hydroxyphenyl)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one: synthesis steps and process conditions Like embodiment one (3), the difference is that 4-trifluoromethylbenzaldehyde is a raw material;

[0068] (4) Intermediate (E)-1-(4-(2-bromoethoxy)phenyl)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one Synthesis: Synthetic steps and process conditions are as embodiment one (4);

[0069] (5) Target product (E)-1-(4-(2-(quinazolin-4-ylthio)ethoxy)phenyl)-3-(4-(trifluoromethyl)phenyl) Synthesis of prop-2...

Embodiment 3

[0070] Embodiment three: (E)-3-(2-Chloro-6-fluorophenyl)-1-(4-(2-(quinazolin-4-ylthio)ethoxy)phenyl)prop-2-ene- 1-keto (compound number is M 3 )Synthesis:

[0071] (1) Synthesis of intermediate 4-chloroquinazoline: synthetic steps and process conditions are the same as embodiment one (1);

[0072] (2) Synthesis of intermediate 4-mercaptoquinazoline: synthetic steps and process conditions are the same as embodiment one (2);

[0073] (3) Synthesis of intermediate (E)-1-(4-hydroxyphenyl)-3-(2-chloro-6-fluorophenyl)prop-2-en-1-one: the synthesis steps and process conditions are the same As in embodiment one (3), the difference is that 2-chloro-6-fluorobenzaldehyde is a raw material;

[0074] (4) Synthesis of intermediate (E)-1-(4-(2-bromoethoxy)phenyl)-3-(2-chloro-6-fluorophenyl)prop-2-en-1-one : synthetic steps and processing conditions are as embodiment one (4);

[0075] (5) Target product (E)-3-(2-chloro-6-fluorophenyl)-1-(4-(2-(quinazolin-4-ylthio)ethoxy)phenyl)propane ...

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Abstract

The invention discloses a compound with an effect of resisting plant viruses, namely a preparation method and biological activity for a chalcone derivative containing quinazoline thioether. The preparation method is used for synthesizing chalcone derivative containing quinazoline thioether by using vairous aromatic aldehydes, p-hydroxy phenyl ethyl ketone, o-aminobenzoic acid, formamide, thionyl chloride, potassium hydroxide and potassium carbonate as raw materials through six steps. The compounds M2, M6, M9 and M22 have relatively high protection, passivation and treatment effect to a tobacco mosaic virus (TMV), and can be used for preparing a novel pesticide for preventing plant virus diseases. According to a formula shown in the description, R is a benzene ring, a substituted aromatic ring and a substituted heterocyclic ring, o-position, m-position and p-position on the aromatic ring comprise one or more of methoxy groups, nitryl, methyl, trifluoromethyl, 2-chlorine-5-nitryl as well as halogen atoms; the halogen atoms can be fluorine, chlorine, bromine and iodine; the heterocyclic ring is a five-member ring, a substituted five-member ring or a six-member ring.

Description

technical field [0001] The invention relates to a novel chalcone derivative containing quinazoline sulfide with anti-plant virus effect and a preparation method thereof. Background technique [0002] Plant virus diseases are rampant and difficult to prevent and control. They are called plant "cancers". Due to its unclear mechanism of action, the lack of effective prevention and control technology and efficient antiviral agents, the occurrence area of ​​plant viral diseases has been expanding in recent years, seriously reducing crop yield and affecting crop quality. According to statistics, due to the harm of plant virus diseases, the loss of food crops in the world reaches 60 billion US dollars every year. In view of the fact that the area of ​​plant virus diseases is constantly expanding and the economic loss is huge, and there is a lack of green and efficient control agents, it is increasingly important to screen green, high-efficiency and low-residue antiviral compounds....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/93C07D409/12A01P1/00
CPCA01N43/54C07D239/93C07D401/12C07D409/12
Inventor 胡德禹万治华宋宝安薛伟金林红李向阳谢丹丹张伟莹
Owner GUIZHOU UNIV
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