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Glucoside-1,4-pentadiene-3-ketone compounds containing acetoxyl groups as well as preparation method and use of glucoside-1,4-pentadiene-3-ketone compounds

A kind of technology of acetoxyglucose and ketone compounds, applied in the field of chemistry

Active Publication Date: 2015-04-08
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

No glycoside-containing pentadienone compounds with anti-plant virus activity have been reported so far

Method used

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  • Glucoside-1,4-pentadiene-3-ketone compounds containing acetoxyl groups as well as preparation method and use of glucoside-1,4-pentadiene-3-ketone compounds
  • Glucoside-1,4-pentadiene-3-ketone compounds containing acetoxyl groups as well as preparation method and use of glucoside-1,4-pentadiene-3-ketone compounds
  • Glucoside-1,4-pentadiene-3-ketone compounds containing acetoxyl groups as well as preparation method and use of glucoside-1,4-pentadiene-3-ketone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] Embodiment one: compound (1 E ,4 E )-1-(4-(2,3,4,6-four- O -Acetyl- β- Synthesis of D-glucopyranoside)oxyphenyl)-5-phenyl-1,4-pentadien-3-one:

[0088] (1) Intermediate ( E )-4-(4-hydroxyphenyl)-3-buten-2-one: Add 16.4 mmol p-hydroxybenzaldehyde and 164 mmol acetone to a 50 mL three-necked flask, slowly add 18 mL of 1 mol / L sodium hydroxide solution, stirred at room temperature for 14 hours, then stopped the reaction, poured the reaction solution into 20mL of ice water, adjusted the pH to 5~6 with dilute hydrochloric acid, a large amount of yellow solids precipitated, and then stirred for 0.5 hours , suction filtered, washed with water, dried, and then recrystallized with ethyl acetate;

[0089] (2) Intermediate (1 E ,4 E )-1-phenyl-5-(4-hydroxyphenyl)-1,4-pentadien-3-one synthesis: add 5 mmol ( E )-4-(4-hydroxyphenyl)-3-buten-2-one), 5.5 mmol benzaldehyde, 15 mL absolute ethanol, slowly drop 0.5 g sodium hydroxide solution in 2 mL at room temperature, and stir ...

Embodiment 2

[0091] Embodiment two: (1 E ,4 E )-1-(2-(2,3,4,6-four- O -Acetyl- β- Synthesis of D-glucopyranoside)oxyphenyl)-5-phenyl-1,4-pentadien-3-one:

[0092] (1) Intermediate ( E )-4-(2-hydroxyphenyl)-3-buten-2-one synthesis: the synthesis steps and process conditions are the same as in Example 1 (1), the difference is that o-hydroxybenzaldehyde is a raw material;

[0093] (2) Intermediate (1 E ,4 E )-1-phenyl-5-(2-hydroxyphenyl)-1,4-pentadien-3-one synthesis: the synthesis steps and process conditions are the same as in Example 1 (2);

[0094] (3) Target product (1 E ,4 E )-1-(2-(2,3,4,6-four- O -Acetyl- β- Synthesis of D-glucopyranoside)phenyl)-5-phenyl-1,4-pentadien-3-one: the synthesis steps and process conditions are the same as in Example 1 (3).

Embodiment 3

[0095] Embodiment three: compound (1 E ,4 E )-1-(4-(2,3,4,6-four- O -Acetyl- β- Synthesis of D-glucopyranoside)phenyl)-5-(4-fluorophenyl)-1,4-pentadien-3-one:

[0096] (1) Intermediate ( E )-4-(4-hydroxyphenyl)-3-buten-2-one synthesis: the synthesis steps and process conditions are the same as Example 1 (1);

[0097] (2) Intermediate (1 E ,4 E )-1-(4-fluorophenyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one synthesis: the synthesis steps and process conditions are the same as in Example 1 (2); The difference is that p-fluorobenzaldehyde is used as raw material;

[0098] (3) Target product (1 E ,4 E )-1-(4-(2,3,4,6-four- O -Acetyl- β- Synthesis of D-glucopyranoside)phenyl)-5-(4-fluorophenyl)-1,4-pentadien-3-one: the synthesis steps and process conditions are the same as in Example 1 (3).

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Abstract

The invention discloses a preparation method of compounds for preventing and controlling plant virus disease: glucoside-1,4-pentadiene-3-ketone compounds containing acetoxyl groups and bioactivity, namely the compounds shown in the general formula (b) and a preparation method thereof. According to the preparation method, the glucoside-1, 4-pentadiene-3-ketone compounds containing the acetoxyl groups are synthesized by taking acetone, 2 or 4-substituted hydroxybenzaldehyde, substituted arylamine and acetyl bromoglucose as raw materials, ethanol and dichloromethane as solvents, dichloromethane as a catalyst and tetrabutylammonium bromide as a phase transfer catalyst. The compounds (f6), (f8), (f10), (f26) and (f28) have relatively good inhibitory effects on tobacco mosaic virus, cucumber mosaic virus and the like. The formula is shown in the description.

Description

technical field [0001] The invention relates to the field of chemical technology, in particular to a compound containing acetoxyglucoside-1,4-pentadien-3-one, a synthesis method of the compound and a method for treating tobacco mosaic virus disease and cucumber mosaic virus. disease, southern rice black-streaked dwarf virus and rice stripe blight virus. Background technique [0002] Plant virus disease is the second largest disease after fungus. Because of its serious harm and difficult control, it is often called "plant cancer". At present, inhibitors such as Ningnanmycin, morpholinidine hydrochloride, ribavirin and amino oligosaccharides are widely used to prevent and control plant virus diseases, but these agents have problems such as poor control effect and high use cost. Therefore, there is an urgent need to create new high-efficiency, low-toxic anti-plant virus agents to meet the needs of agricultural production. [0003] Natural products have the characteristics of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/203C07H15/26C07H1/00A01P1/00
CPCA01N43/16A01N43/40C07H1/00C07H15/203C07H15/26
Inventor 宋宝安陈美航胡德禹薛伟李向阳张国平李天先张伟莹
Owner GUIZHOU UNIV
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