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4-acetylamino benzene sulfonyl substituted 3,5-bis(arylidene)-4-piperidinone compounds and preparation method thereof

An acetamidobenzenesulfonyl and diarylmethylene technology is applied in the field of anti-tumor and anti-inflammatory drugs and their preparation, and can solve the problem of less anti-inflammatory activity, less compound reports, structure-activity relationship, and anti-tumor and anti-inflammatory activities Lack of systemicity and other problems, to achieve the effects of mild reaction conditions, high synthesis yield, and easy operation

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

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Problems solved by technology

[0007] Nevertheless, the reported 3,5-bis(arymethylene)-4-piperidone derivatives are all symmetrical compounds. Pyridone compounds are rarely reported
In addition, there are few reports on the anti-inflammatory activity of such compounds
If different substituents are introduced on both sides of 3,5-diaryl methylene-4-piperidone, especially substituents with different electron-withdrawing and electron-donating abilities, such as electron-withdrawing groups fluorine, nitro, The cyano group, etc., the electron-withdrawing group methoxy group, etc., may affect the polarity, solubility, anti-tumor activity, anti-inflammatory activity, and bioavailability of the molecule, and the asymmetric 3,5- Lack of systematic analysis of structure-activity relationships and antitumor and anti-inflammatory activities of diarylmethylene-4-piperidinones

Method used

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  • 4-acetylamino benzene sulfonyl substituted 3,5-bis(arylidene)-4-piperidinone compounds and preparation method thereof
  • 4-acetylamino benzene sulfonyl substituted 3,5-bis(arylidene)-4-piperidinone compounds and preparation method thereof
  • 4-acetylamino benzene sulfonyl substituted 3,5-bis(arylidene)-4-piperidinone compounds and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0030] 3-(3,4,5-trimethoxybenzylidene)-5-(2-fluorobenzylidene)-N-(4-acetylaminobenzenesulfonyl)-4-piperidone (BAP- 1) Synthesis of

[0031] Mix 0.01mol of 4-piperidone hydrochloride with 0.01mol of 2-fluorobenzaldehyde and 0.01mol of 3,4,5-trimethoxybenzaldehyde in 10mL of acetic acid, and continuously feed dry hydrogen chloride gas for 45min , stirred at room temperature for 15 hours, and determined the end point of the reaction by thin layer chromatography (TLC). After the reaction, the precipitate was suction filtered, the precipitate was dissolved in water and the pH value was adjusted to neutrality with sodium hydroxide solution, and the resulting precipitate was chromatographed on a 200-300 mesh silica gel column (eluent: petroleum ether / ethyl acetate / methanol=10: 10:1) to obtain a yellow solid, namely the intermediate BAP-H (1), then, the intermediate BAP-H (1) and 4-acetylaminobenzenesulfonyl chloride were dissolved in 10mL of dichloromethane, and 3-5 drops of Pyridi...

Embodiment 2

[0034] 3-(3,5-dimethoxybenzylidene)-5-(2-fluorobenzylidene)-N-(4-acetylaminobenzenesulfonyl)-4-piperidone (BAP-2 ),Synthesis

[0035] Mix 0.01mol of 4-piperidone hydrochloride with 0.01mol of 2-fluorobenzaldehyde and 0.01mol of 3,5-dimethoxybenzaldehyde in 10mL of acetic acid, and continuously feed dry hydrogen chloride gas for 45min. The reaction was stirred at room temperature for 15 hours, and the end point of the reaction was determined by thin layer chromatography (TLC). 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 obtained precipitate was chromatographed on a 200-300 mesh silica gel column (eluent: petroleum ether / ethyl acetate = 2:1) Obtain a yellow solid, namely the intermediate BAP-H (2), then, dissolve the intermediate BAP-H (2) and 4-acetylaminobenzenesulfonyl chloride in 10 mL of dichloromethane, add 3-5 drops of pyridine, and stir a...

Embodiment 3

[0038] Synthesis of 3-(3-nitrobenzylidene)-5-(2-fluorobenzylidene)-N-(4-acetylaminobenzenesulfonyl)-4-piperidinone (BAP-3)

[0039] Mix 0.01mol of 4-piperidone hydrochloride with 0.01mol of 2-fluorobenzaldehyde and 0.01mol of 3-nitrobenzaldehyde in a solution of 15mL of methanol and water, add dropwise 2-3mL of 20% sodium hydroxide The solution was stirred and reacted at 40° C. for 6 hours, and 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 chromatographed on a 200-300 mesh silica gel column (eluent: petroleum ether / ethyl acetate = 1:1) to obtain a yellow solid, which is the intermediate BAP-H (3). Then, Dissolve the intermediate BAP-H(3) and 4-acetylaminobenzenesulfonyl chloride in 10 mL of dichloromethane, add 3-5 drops of pyridine, stir overnight at room temperature, and determine the end point of the reaction by thin layer chromatography (TLC). The...

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Abstract

The invention relates to seven 4-acetylamino benzene sulfonyl substituted 3,5-bis(arylidene)-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 4-acetylamino benzene sulfonyl substituted 3,5-bis(arylidene)-4-piperidinone compounds comprises the following steps: firstly, respectively performing claisen-schmidt condensation reaction on 4-piperidinone hydrochloride and two aromatic aldehyde and performing column chromatography to obtain a 3,5-bis(arylidene)-N-H-4-piperidinone hydrochloride intermediate product (BAP-H) having different substituents; then performing benzene sulfonylation on the 3,5-bis(arylidene)-N-H-4-piperidinone hydrochloride intermediate product and 4-acetylsulphanilyl chloride to obtain the 4-acetylamino benzene sulfonyl substituted 3,5-bis(arylidene)-4-piperidinone compounds (BAP). The compounds have good anti-tumor and anti-inflammatory activities, can avoid the genetic toxicity of currently-used anti-tumor medicines, has little toxicity to normal cells, and also has 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 4-acetylaminobenzenesulfonyl-substituted 3,5-diaryl methylene-4-piperidone compounds with anti-tumor and anti-inflammatory activities, which belong to anti-tumor and anti-inflammatory drugs and their preparation methods technology field. 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 mi...

Claims

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Application Information

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IPC IPC(8): C07D211/96A61P35/00A61P29/00
CPCC07D211/96Y02P20/584
Inventor 侯桂革王春华李宁姚彬荣
Owner BINZHOU MEDICAL COLLEGE
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