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Piperazine-containing ferulic acid derivative and preparation method and application thereof

A derivative, the technology of ferulic acid, is applied in the field of drug synthesis and agricultural protection to achieve the effects of improving pharmacokinetic properties, easy metabolism and degradation, and increasing alkalinity and water solubility

Active Publication Date: 2021-10-01
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In summary, small drug molecules containing ferulic acid and piperazine structures have broad-spectrum biological activities. According to the investigation of previous literatures, there is no introduction of piperazine active groups into the structure of ferulic acid and anti-inflammatory effects. Research Report on the Activity of Plant Viruses

Method used

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  • Piperazine-containing ferulic acid derivative and preparation method and application thereof
  • Piperazine-containing ferulic acid derivative and preparation method and application thereof
  • Piperazine-containing ferulic acid derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Example 1: (E)-1-(4-benzylpiperazin-1-yl)-3-(4-((2-fluorobenzyl)oxy)-3-methoxyphenyl)propane- The preparation method of 2-en-1-one (compound number is C1), comprises the following steps:

[0063] (1) Preparation of trans methyl ferulate

[0064] 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, the organic phases were combined, and concentrated under reduced pressure to obtain 19.08 g of a viscous liquid with a yield of 88.97%.

[0065] (2) Preparation of (E)-3-(4-((2-fluorobe...

Embodiment 2

[0075]Example 2: (E)-3-(4-((2-fluorobenzyl)oxy)-3-methoxyphenyl)-1-(4-(2-oxo-2-phenylethyl) Base) piperazin-1-yl) prop-2-en-1-one (compound number is the preparation method of C2), comprises the following steps:

[0076] Step (1)~(5) is the same as embodiment 1

[0077] (6) Add (E)-3-(4-((2-fluorobenzyl)oxy)-3-methoxyphenyl)-1-(piperazin-1-yl) to a 50mL round bottom flask ) prop-2-en-1-one (0.30g, 0.81mmoL) and methylene chloride solution, stirred at room temperature, and then slowly added α-bromoacetophenone (0.16g, 0.81mmoL) into the system. After the reaction was completed, concentrated under reduced pressure to obtain a viscous product, which was purified by silica gel column chromatography with petroleum ether / ethyl acetate = 1:3 (V / V) as the eluent to obtain 0.24 g of an oily compound with a yield of 49.84 %.

Embodiment 3

[0078] Example 3: (E)-3-(4-isopropoxy-3-methoxyphenyl)-1-(4-(2-methoxybenzyl)piperazin-1-yl)propane- The preparation method of 2-en-1-one (compound number is C3), comprises the following steps:

[0079] Step (1)~(5) is the same as embodiment 1

[0080] (6) Add (E)-3-(4-isopropoxy-3-methoxyphenyl)-1-(piperazin-1-yl)prop-2-ene- A solution of 1-ketone (0.30 g, 0.99 mmoL) and methylene chloride was stirred at room temperature, and then o-methylbenzyl chloride (0.14 g, 0.99 mmoL) was slowly added to the system. After the reaction, concentrated under reduced pressure to obtain a viscous product, which was purified by silica gel column chromatography with petroleum ether / ethyl acetate = 1:3 (V / V) as the eluent to obtain 0.23 g of an oily compound with a yield of 57.12 %.

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Abstract

The invention discloses a piperazine-containing ferulic acid derivative and a preparation method and application thereof, and belongs to the technical field of drug synthesis and agricultural disease control, the structural general formula of the piperazine-containing ferulic acid derivative is shown in the specification, in the formula, R1 is ethyl, allyl, isopropyl, propynyl, benzyl, o-methylbenzyl, m-methylbenzyl and o-fluorobenzyl; R2 is ethyl sulfonyl, 4-methyl benzenesulfonyl, 4-nitrobenzenesulfonyl, 4-trifluoromethyl benzenesulfonyl, 4-fluorobenzenesulfonyl, 2, 5-dichlorobenzenesulfonyl, 4-bromobenzenesulfonyl, 4-bromine-3-trifluoromethyl benzenesulfonyl, 3-trifluoromethyl benzoyl, 4-fluorobenzoyl, 2-fluorobenzoyl, 4-methoxybenzoyl, 5-chlorovaleryl, 4-chlorobutyryl, 4-fluorobenzyl, 2-methoxybenzyl, 3, 4, 4-trifluorobutyl-3-alkene 1-yl, 2-methoxy-2-oxoethyl, 2-oxo-2-phenylethyl. The drug molecule is high in activity, the inhibitory activity on TMV and CMV is remarkable, the structure of the drug is derived from natural products, and the drug is environmentally friendly, easy to metabolize and degrade, simple and safe in preparation process and relatively stable in physicochemical property.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis and agricultural protection, and specifically relates to a piperazine-containing ferulic acid derivative, and also relates to a preparation method of the piperazine-containing ferulic acid derivative, and its use in anti-plant virus Applications. Background technique [0002] Plant virus disease is the second largest type of plant disease after fungi in agricultural production. In recent years, the prevalence and outbreak of plant virus diseases pose a serious threat to crop yield and quality. Common plant viruses in agricultural production include tobacco mosaic virus (TMV), cucumber mosaic virus (CMV) and pepper mild mottle virus (PMMoV). The economic losses caused by plant virus diseases are as high as 20 billion US dollars. Because viruses are absolutely parasitic in plants, it is difficult to prevent and control plant virus diseases. At present, the main way to prevent and treat pl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/182C07D295/192C07D295/26A01N43/60A01P1/00
CPCC07D295/182C07D295/192C07D295/26A01N43/60Y02A50/30
Inventor 甘秀海袁婷刘丹宋宝安胡德禹
Owner GUIZHOU UNIV
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