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A kind of α-chalcone malonate derivative containing pyridine heterocycle and its preparation method and application

A technology of chalcone malonic acid and pyridine heterocycle, which is applied in the field of chemistry and can solve the problems of few research reports on plant virus resistance and the like

Active Publication Date: 2017-01-25
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But for pyridine-containing heterocycles α - Chalcone malonate derivatives have not yet been synthesized, and there are relatively few domestic and foreign research reports on the anti-plant virus of this type of compound

Method used

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  • A kind of α-chalcone malonate derivative containing pyridine heterocycle and its preparation method and application
  • A kind of α-chalcone malonate derivative containing pyridine heterocycle and its preparation method and application
  • A kind of α-chalcone malonate derivative containing pyridine heterocycle and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Example 1, Diethyl 2-(1-(4-((6-chloropyridin-3-yl)methoxy)phenyl)-3-oxo-3-phenyl)propyl)malonate Synthesis (compound number is a):

[0055] (1) Synthesis of 4-hydroxychalcone:

[0056] Add acetophenone (2.40g, 20 mmol) and p-hydroxybenzaldehyde (2.44g, 20 mmol) into a 100 mL single-necked bottle, add 10 mL of absolute ethanol to dissolve the solid, start stirring, and the reaction system is light yellow and transparent liquid, 20% sodium hydroxide (2.00g, 50mmol) solution was added dropwise, and the reaction system was a reddish-brown liquid. Stir at room temperature, follow the reaction process by TLC, stop the reaction after the disappearance of the raw material point, pour the reaction system into ice water and adjust the pH=4~5 with dilute hydrochloric acid, a yellow solid is precipitated, and the crude product is obtained by suction filtration and drying. Recrystallization from water and ethanol gave the target compound as a yellow solid, with a mass of 3.01 g (t...

Embodiment 2

[0063] Example 2, Dimethyl 2-(1-(4-((6-chloropyridin-3-yl)methoxy)phenyl)-3-oxo-3-phenyl)propyl)malonate Synthesis (compound number is b):

[0064] (1) Synthesis of 4-hydroxychalcone:

[0065] Synthesize as in Example 1 (1) method and conditions.

[0066] (2) Synthesis of 4-(6-chloropyridin-3-yl)methoxychalcone Synthesis:

[0067] Synthesize as in Example 1 (2) method and conditions.

[0068] (3) Dimethyl 2-(1-(4-((6-chloropyridin-3-yl)methoxy)phenyl)-3-oxo-3-phenyl-propyl)malonate synthesis:

[0069] Synthesize as in Example 1 (3) method and conditions, the difference is that dimethyl malonate (0.20g, 1.5mmol) is added, and anhydrous methanol is used as a solvent to obtain 2-(1-(4-((6-chloro Pyridin-3-yl)methoxy)phenyl)-3-oxo-3-phenyl)propyl)malonate dimethyl ester mass 0.19g (theoretical mass 0.24g), yield 77.2%.

Embodiment 3

[0070] Example 3, 2-(1-(4-((6-chloropyridin-3-yl)methoxy)phenyl)-3-oxo-3-(4-methoxyphenyl)propyl) Synthesis of diethyl malonate (compound number is c):

[0071] (1) Synthesis of 4-hydroxyl-4'-methoxychalcone:

[0072]Synthesize as in Example 1 (1) method and conditions, the difference is that 4-methoxyacetophenone (3.00g, 20mmol) is added to obtain 2.90g of 4-hydroxyl-4'-methoxychalcone (theoretical mass 5.09g), yield 57.0%.

[0073] (2) Synthesis of 4-(6-chloropyridin-3-yl)methoxy-4'-methoxychalcone:

[0074] Synthesized as in Example 1 (2) method and conditions, the difference is that 4-hydroxy-4'-methoxychalcone (0.64g, 2.5mmol) was added to obtain 4-(6-chloropyridin-3-yl)methanol Oxygen-4'-methoxychalcone mass 0.70g (theoretical mass 0.95g), yield 72.5%.

[0075] (3) 2-(1-(4-((6-chloropyridin-3-yl)methoxy)phenyl)-3-oxo-3-(4-methoxyphenyl)propyl)propyl Synthesis of diethyl diacid:

[0076] Synthesized according to the method and conditions of Example 1 (3), the differ...

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Abstract

The invention discloses a compound capable of preventing and controlling plant virus disease, namely a pyridine-heterocycle-containing alpha-chalcone malonate derivative, as well as a preparation method and biological activity thereof. The pyridine-heterocycle-containing alpha-chalcone malonate derivative can be shown in a general formula (I) (described in the specification). According to the preparation method of the pyridine-heterocycle-containing alpha-chalcone malonate derivative, substituted phenylethanone, p-hydroxy benzaldehyde, absolute ethyl alcohol, sodium hydroxide, hydrochloric acid, 2-chloro-5-chloromethyl pyridine, acetone, potassium carbonate, potassium hydroxide and diethyl (dimethyl) malonate are taken as raw materials, and a target compound is synthesized by carrying out three-step reaction. The compounds a, d, o, e and w have good inhibiting effect on cucumber mosaic viruses and tobacco mosaic viruses. The general formula (I) is described in the specification.

Description

technical field [0001] The present invention relates to the field of chemical technology, in particular to a pyridine heterocyclic compound α- Chalcone malonate derivatives, the preparation method of the compound and the application of inhibiting cucumber mosaic virus disease, tobacco mosaic virus disease, southern rice black-streaked dwarf virus disease and rice stripe leaf blight virus. Background technique [0002] Chalcones are a class of natural organic substances present in medicinal plants such as licorice and safflower. They have the characteristics of low toxicity and low residue, and because of their greater flexibility in molecular structure, they can interact with different receptors. Combined, it exhibits a wide range of biological activities, such as: antibacterial, antiviral, nematicidal, antiallergic and other biological activities. Therefore, chalcones have potential research value in the field of new pesticide synthesis. Secondly, pyridine is a very old a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/61A01P1/00
CPCC07D213/61
Inventor 宋宝安陈志伟胡德禹薛伟金林红董良瑞张伟莹潘建科罗亮指
Owner GUIZHOU UNIV