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Amide-containing ferulic acid derivative as well as preparation method and application thereof

A technology of ferulic acid and derivatives, applied in the field of amide-containing ferulic acid derivatives and their preparation, can solve the problems of low antiviral activity, single structure, low anti-CMV activity of ferulic acid derivatives, etc. Antiviral activity, simple preparation process and stable physical and chemical properties

Pending Publication Date: 2022-03-18
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, ferulic acid derivatives have less anti-CMV activity, single structure, low antiviral activity, and insufficient ability to prevent and control plant virus diseases.

Method used

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  • Amide-containing ferulic acid derivative as well as preparation method and application thereof
  • Amide-containing ferulic acid derivative as well as preparation method and application thereof
  • Amide-containing ferulic acid derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] (E)-2-(3-(allyloxy)-3-methoxyphenyl)acryloyl)-N-(4-(trifluoromethyl)phenyl)hydrazine-1-carbon thioamide (compound number is I1) preparation method, comprises the following steps:

[0081]

[0082] (1) Preparation of trans methyl ferulate

[0083] In a 250mL three-necked flask, add trans-ferulic acid (20.00g, 102.99mmoL) and 100mL of anhydrous methanol solution, after stirring at room temperature for 5min, slowly add concentrated H 2 SO 4 (10.10g, 102.99mmoL), the temperature was raised to 50°C. After the reaction was completed, the methanol solution was removed under reduced pressure, and then 40 mL of water was added to the system, which was adjusted with saturated sodium bicarbonate solution until no bubbles were generated. Finally, it was extracted three times with dichloromethane, and the organic phases were combined and concentrated under reduced pressure to obtain 19.08 g of a viscous liquid with a yield of 88.9%.

[0084] (2) Preparation of (E)-3-(4-(allyl...

Embodiment 2

[0093] (E)-2-(3-(4-ethoxy-3-methoxyphenyl)acryloyl)-N-(3-(methylthio)propyl)hydrazine-1-carbon thioamide ( Compound number is the preparation method of II 2), comprising the following steps:

[0094] Step (1)~(4) is the same as embodiment 1

[0095] (5) Add (E)-3-(4-ethoxy-3-methoxyphenyl)acrylohydrazide (0.50g, 2.12mmoL), 1-isothiocyanato - 4-toluene (0.31g, 2.12mmoL) and dry ethanol solution, stirred at room temperature. After the reaction, add saturated sodium bicarbonate solution to the system, use dichloromethane to extract three times 30mL each time, combine the organic phases, and use anhydrous sodium sulfate to dry, concentrate under reduced pressure and go through silica gel column chromatography, with petroleum ether / Ethyl acetate=3:1 (V / V) was used as the eluent for purification to obtain 0.19 g of white solid with a yield of 49.5%.

Embodiment 3

[0097] (E)-2-(3-(allyloxy)-3-methoxyphenyl)acryloyl)-N-(4-(trifluoromethyl)phenyl)hydrazine-1-carbon thioamide (the compound number is II1) preparation method, comprises the following steps:

[0098]

[0099] (1) Preparation of trans methyl ferulate

[0100] In a 250mL three-necked flask, add trans-ferulic acid (20.00g, 102.99mmoL) and 100mL of anhydrous methanol solution, after stirring at room temperature for 5min, slowly add concentrated H 2 SO 4 (10.10g, 102.99mmoL), the temperature was raised to 50°C. After the reaction was completed, the methanol solution was removed under reduced pressure, and then 40 mL of water was added to the system, which was adjusted with saturated sodium bicarbonate solution until no bubbles were generated. Finally, it was extracted three times with dichloromethane, and the organic phases were combined and concentrated under reduced pressure to obtain 19.08 g of a viscous liquid with a yield of 88.9%.

[0101] (2) Preparation of (E)-3-(4-i...

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Abstract

The invention belongs to the technical field of drug synthesis and agricultural disease control, and particularly relates to an amide-containing ferulic acid derivative as well as a preparation method and application thereof. The synthesized amide-containing ferulic acid derivative compound can be applied to preparation of plant virus resisting agents and can effectively inhibit diseases such as tomato spotted wilf virus and cucumber mosaic virus disease. The compounds Y1, Y2, Y8, Z1 and Z2 in the amide-containing ferulic acid derivative disclosed by the invention show relatively good inhibitory activity on tomato spotted wilf virus and cucumber mosaic virus. Wherein the compound Y2 shows relatively good passivation activity on tomato spotted wilf virus and cucumber mosaic virus, and is superior to positive control medicaments such as ferulic acid, ningnanmycin and virazole. The compound can be used as a medicine or medicament for preventing and treating diseases such as tomato spotted wilf virus and cucumber mosaic virus. The structure of the material is derived from natural products, and the material is environment-friendly, easy to metabolize and degrade, simple in preparation process, relatively stable in physicochemical property and wide in application prospect.

Description

technical field [0001] The invention belongs to the technical fields of drug synthesis and agricultural disease prevention and control, and in particular relates to an amide-containing ferulic acid derivative and its preparation method and application. Background technique [0002] In recent years, with the prevalence and outbreak of plant virus diseases, plant virus diseases pose a serious threat to crop yield and quality in my country. The more common plant viruses in agricultural production include tomato spotted wilt virus (Tomato spotted wilt virus, TSWV), cucumber mosaic virus (Cucumber mosaic virus, CMV), etc., and the economic losses caused by plant virus diseases are as high as 20 billion US dollars every year. Because viruses are absolutely parasitic in plants, it is difficult to prevent and control plant virus diseases. At present, the main control agents are Ningnanmycin and ribavirin, but the field control effect of Ningnanmycin and ribavirin is not ideal. The...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C337/06C07C335/26C07C235/34C07C241/04C07C243/32C07C51/09C07C67/08C07C67/31C07C69/734C07C51/60C07C59/64C07C331/32C07C231/02C07C231/12A01N47/34A01N37/46A01P1/00
CPCC07C337/06C07C335/26C07C235/34C07C241/04C07C51/09C07C67/08C07C67/31C07C51/60C07C331/32C07C231/02C07C231/12A01N47/34A01N37/46A01P1/00C07C69/734C07C59/64C07C243/32Y02P20/55
Inventor 甘秀海袁婷韦兴品陈超兰世超
Owner GUIZHOU UNIV
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