3,5-bis(arylidene)-N-benzenesulfonyl-4-piperidinone compounds and preparation method thereof

A technology of diaryl methylene and acetamidobenzenesulfonyl, which is applied in the field of anti-tumor and anti-inflammatory drugs and their preparation, can solve the problems of less research on benzenesulfonylation modification, and achieve favorable promotion and mild reaction conditions , the effect of high synthesis yield

Active Publication Date: 2018-06-22
BINZHOU MEDICAL COLLEGE
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In comparison, there are many researches and products on aliphatic acylation, aromatic acylation and phosphorylation of 3,5-diarylmethylene-4-piperidinone, while 3,5-diarylmethylene There are relatively few studies on the benzenesulfonylation of methyl-4-piperidone

Method used

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  • 3,5-bis(arylidene)-N-benzenesulfonyl-4-piperidinone compounds and preparation method thereof
  • 3,5-bis(arylidene)-N-benzenesulfonyl-4-piperidinone compounds and preparation method thereof
  • 3,5-bis(arylidene)-N-benzenesulfonyl-4-piperidinone compounds and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Synthesis of 3,5-bis(2-fluorobenzylidene)-N-(4-fluorobenzenesulfonyl)-4-piperidone (BAP-1)

[0033] Mix 0.01mol of 4-piperidone hydrochloride and 0.02mol of 2-fluorobenzaldehyde in a solution of 15mL of methanol and water, add 2-3mL of 20% sodium hydroxide solution dropwise at room temperature, and stir at 50°C for 6 hours , The end point of the reaction was determined by thin layer chromatography (TLC). After the reaction, the precipitate was suction filtered, and the resulting precipitate was washed with 70% aqueous methanol to obtain a yellow solid, namely the intermediate BAP-H (1). Then, the intermediate BAP-H (1) and 4-fluorobenzenesulfonyl chloride were dissolved in 10 mL Add 3-5 drops of pyridine to dichloromethane, stir overnight at room temperature, and determine the reaction end point by thin layer chromatography (TLC). The reaction solution was washed twice with 2mol / L=10:10:1) hydrochloric acid solution, and the reaction solution was concentrated under red...

Embodiment 2

[0036] Synthesis of 3,5-bis(3-nitrobenzylidene)-N-(4-fluorobenzenesulfonyl)-4-piperidone (BAP-2)

[0037] Mix 0.01mol of 4-piperidone hydrochloride and 0.02mol of 3-nitrobenzaldehyde in a solution of 15mL of methanol and water, add 2-3mL of 20% sodium hydroxide solution dropwise at room temperature, and stir at 40°C The reaction was carried out for 6 hours, and the end point of the reaction was determined by thin layer chromatography (TLC). After the reaction was completed, the precipitate was suction-filtered, and the resulting precipitate was washed with 70% aqueous methanol to obtain a yellow solid, the intermediate BAP-H (2). Then, the intermediate BAP-H (2) and 4-fluorobenzenesulfonyl chloride were dissolved in 10 mL Add 3-5 drops of pyridine to dichloromethane, stir overnight at room temperature, and determine the reaction end point by thin layer chromatography (TLC). The reaction solution was washed twice with 2mol / L hydrochloric acid solution, concentrated under reduc...

Embodiment 3

[0040] Synthesis of 3,5-bis(4-cyanobenzylidene)-N-(4-fluorobenzenesulfonyl)-4-piperidinone (BAP-3)

[0041] 0.01mol of 4-piperidone hydrochloride and 0.02mol of 4-cyanobenzaldehyde were mixed in 10mL of acetic acid, and dry hydrogen chloride gas was continuously introduced for 45min, stirred and reacted at 25°C for 8 hours, and passed thin layer chromatography ( TLC) to determine the end point of the reaction. After the reaction, the precipitate was suction filtered, the precipitate was dissolved in water and the pH value was adjusted to neutral with sodium hydroxide solution, and the resulting precipitate was washed with 70% methanol aqueous solution to obtain a yellow solid, which was the intermediate BAP-H (3). Then, the intermediate BAP-H(3) and 4-fluorobenzenesulfonyl chloride were dissolved in 10 mL of dichloromethane, 3-5 drops of pyridine were added, stirred at room temperature overnight, and the end point of the reaction was determined by thin layer chromatography (TL...

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Abstract

The invention relates to ten 3,5-bis(arylidene)-N-benzenesulfonyl-4-piperidinone compounds having anti-tumor and anti-inflammatory activities, and belongs to the technical field of anti-tumor and anti-inflammatory medicines. A preparation method of the 3,5-bis(arylidene)-N-benzenesulfonyl-4-piperidinone compounds comprises the following steps: firstly, performing claisen-schmidt condensition reaction on 4-piperidinone hydrochloride and aromatic aldehyde to obtain a 3,5-bis(arylidene)-N-H-4-piperidinone hydrochloride intermediate product so as to further perform benzene sulfonylation on the 3,5-bis(arylidene)-N-H-4-piperidinone hydrochloride intermediate product and a sulfonylation reagent to obtain the 3,5-bis(arylidene)-N-benzenesulfonyl-4-piperidinone compounds. The compounds have good anti-tumor and anti-inflammatory activities, can avoid the genetic toxicity of currently-used anti-tumor medicines, have little toxicity to normal cells, and also have good anti-inflammatory activity.The preparation method is simple and convenient to operate, is mild in reaction conditions, is high in synthetic yield, and is beneficial for being widely popularized in anti-tumor and anti-inflammatory fields.

Description

technical field [0001] The invention relates to a series of 3,5-diarylmethylene-N-benzenesulfonyl-4-piperidone compounds with anti-tumor and anti-inflammatory activities, and belongs to the technical field of anti-tumor and anti-inflammatory drugs and their preparation methods. Background technique [0002] Curcumin is a yellow phenolic pigment obtained from the rhizomes of ginger plants (such as turmeric, zedoary, etc.), because it has anti-inflammatory, antibacterial, anti-tumor, anti-oxidation, anti-protozoal, anti-rheumatism, anti-senile dementia, and anti-aging effects. The functions of liver, gallbladder, pain relief, diuresis, hypoglycemia and stomach invigoration are highly valued by the medical circles at home and abroad. However, due to its poor water solubility, unstable structure, and low bioavailability, its clinical application is seriously affected. Therefore, its structure is optimized and transformed, and the diketone structure in the middle of curcumin is ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/89A61P29/00A61P35/00
CPCC07D213/89Y02P20/55
Inventor 侯桂革王春华李宁姚彬荣丛蔚
Owner BINZHOU MEDICAL COLLEGE
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