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Purine-ring-containing benzene sulfonamide chalcone derivative and preparation and application methods thereof

A technology of chalcones and benzenesulfonamides, which is applied to the chalcone derivatives of benzenesulfonamide chalcones containing purine rings, their preparation and application, and achieves the effects of low production cost, simple production process, and good inhibitory activity

Inactive Publication Date: 2018-11-27
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there has been no report on the anti-plant virus activity

Method used

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  • Purine-ring-containing benzene sulfonamide chalcone derivative and preparation and application methods thereof
  • Purine-ring-containing benzene sulfonamide chalcone derivative and preparation and application methods thereof
  • Purine-ring-containing benzene sulfonamide chalcone derivative and preparation and application methods thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Example 1: (E)-1-(4-((4-methylphenyl)sulfonamido)phenyl)-3-(4-((9-methyl-9H-purin-6-yl) Synthesis of oxy)phenyl)-2-propenyl ketone (compound number A 1 )

[0065] (1) Preparation of N-(4-acetylphenyl)-4-methylbenzenesulfonamide

[0066] Add p-aminoacetophenone (2.00g, 14.80mmol) into a 50mL single-necked flask and add 10mL of dichloromethane, then add pyridine (1.17g, 14.80mmol) to the system, stir at room temperature for 1 hour, the reaction system is orange To the yellow liquid, p-toluenesulfonyl chloride (3.10g, 16.28mmol) was slowly added dropwise, the color of the system deepened, and finally turned into a red clear liquid. The reaction was tracked by thin-layer chromatography, and the reaction was basically complete after 10 hours of reaction. After the reaction, the reaction system was poured into a beaker, washed with water, poured off the water layer, washed repeatedly 5 times, and finally transferred the organic layer containing a small amount of water into ...

Embodiment 2

[0073] Example 2: (E)-1-(4-((4-methylphenyl)sulfonamido)phenyl)-3-(4-((9-ethyl-9H-purin-6-yl) Synthesis of oxy)phenyl)-2-propenyl ketone (compound number A 2 )

[0074] Steps (1)-(2) are the same as in Example 1;

[0075] (3) Preparation of 6-chloro-9-ethyl-9H-purine

[0076] 6-chloropurine (2.00g, 12.94mmol) was added to a 25mL single-necked flask, and 8mL of DMF was added, stirred at room temperature, the system was a yellow liquid, potassium carbonate (3.58g, 25.88mmol) was added to the system, and Stir for half an hour, then slowly add bromoethane (4.23g, 38.82mmol) dropwise to the system, and the reaction is basically complete after 24 hours. After the reaction ends, the reaction system is poured into a beaker, washed with saturated ammonium chloride solution, Then extract with dichloromethane, wash repeatedly 3 times, take the organic layer, dry with anhydrous magnesium sulfate for half an hour, filter, remove the magnesium sulfate solid, rotary steam, remove DMF, obt...

Embodiment 3

[0079] Example 3: (E)-1-(4-((4-methylphenyl)sulfonamido)phenyl)-3-(4-((9-benzyl-9H-purin-6-yl) Synthesis of oxy)phenyl)-2-propenyl ketone (compound number A 3 )

[0080] Steps (1)-(2) are the same as in Example 1;

[0081] (3) Preparation of 6-chloro-9-benzyl-9H-purine

[0082] 6-chloropurine (2.00g, 12.94mmol) was added to a 25mL single-necked flask, and 8mL of DMF was added, stirred at room temperature, the system was a yellow liquid, potassium carbonate (3.58g, 25.88mmol) was added to the system, and Stir for half an hour, and slowly add benzyl chloride (3.28g, 25.88mmol) dropwise to the system. After 24 hours, the reaction is basically complete. After the reaction, the reaction system is poured into a beaker, washed with saturated ammonium chloride solution, and then Extract with dichloromethane, wash repeatedly 3 times, take the organic layer, dry with anhydrous magnesium sulfate for half an hour, filter, remove the magnesium sulfate solid, rotary steam, remove DMF, ob...

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Abstract

The invention discloses a purine-ring-containing benzene sulfonamide chalcone derivative and preparation and application methods thereof. The purine-ring-containing benzene sulfonamide chalcone derivative has a formula (I) shown as below, in which R1 is 4-oxymethyl, 4-tert-butyl, 4-methyl, 4-flouride, 4-bromide, 2-methyl, 2-fluoride, 2-chloride, 2-bromide and hydrogen atom and R2 is methyl, ethyland benzyl. The purine-ring-containing benzene sulfonamide chalcone derivative can inhibit tobacco mosaic virus, cucumber mosaic virus, potato Y virus and southern rice black-streaked dwarf virus.

Description

technical field [0001] The present invention relates to the technical field of chemical engineering, in particular to purine-containing cyclic benzenesulfonamide chalcone derivatives, and to a preparation method of the purine-containing cyclic benzenesulfonamide chalcone derivatives, and to the purine-containing cyclic benzenesulfonamide chalcone derivatives. Application of benzenesulfonamide chalcone derivatives of purine ring in resistance to tobacco mosaic virus disease, cucumber mosaic virus disease, potato Y virus and southern rice black-streaked dwarf virus disease. Background technique [0002] Plant virus disease is a kind of major disease in agricultural production, known as "plant cancer". Its harm to crops is second only to fungal diseases, such as tobacco mosaic virus (TMV), cucumber mosaic virus (CMV), potato virus Y (PVY) and southern rice black-streaked dwarf virus (SRBSDV) are all important worldwide. disease. Because viruses are absolutely parasitic in p...

Claims

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Application Information

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IPC IPC(8): C07D473/30A01N43/90A01P1/00
CPCA01N43/90C07D473/30
Inventor 胡德禹周大贵宋宝安何方成易崇粉王邵波陈吉祥杨玉媛
Owner GUIZHOU UNIV
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