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3,5-Dibenzylidene-4-Piperidinone Derivative for Antitumor and Preparation Method thereof

A technology of benzylidene and trifluoromethylbenzylidene is applied in the field of antitumor drugs and preparation thereof, and achieves the effects of novel structure, great application prospect and avoiding genotoxicity

Active Publication Date: 2016-04-20
BINZHOU MEDICAL COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, studies have also found that such compounds can avoid multidrug resistance by reversing P-glycoprotein, so it is possible to find effective MDR reversal agents from them

Method used

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  • 3,5-Dibenzylidene-4-Piperidinone Derivative for Antitumor and Preparation Method thereof
  • 3,5-Dibenzylidene-4-Piperidinone Derivative for Antitumor and Preparation Method thereof
  • 3,5-Dibenzylidene-4-Piperidinone Derivative for Antitumor and Preparation Method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis of 3,5-bis(4-trifluoromethylbenzylidene)-4-piperidinone a

[0030] Mix 0.005mol of 4-piperidone hydrochloride and 0.01mol of 4-trifluoromethylbenzaldehyde in 12.5mL of glacial acetic acid, pass through dry HCl gas at room temperature for 60min, stir for 8h, and pass thin-layer chromatography Thin layer analysis (TLC) was used to determine the end point of the reaction. After completion of the reaction, suction filtration, the resulting precipitate was added to a mixture of 12.5 mL of potassium carbonate solution with a mass fraction of 25% and 12.5 mL of acetone solution, stirred at room temperature for 0.5 h, suction filtration, and recrystallized with a mixed solvent of methanol and chloroform to obtain 3, 5-bis(4-trifluoromethylbenzylidene)-4-piperidone 1.21g, yield 59%.

[0031]

Embodiment 2

[0033] Synthesis of N-(4-nitrobenzoyl)-3,5-bis(4-trifluoromethylbenzylidene)-4-piperidone b

[0034] Mix 2 mL of 25% NaOH solution with 1 mmol of 3,5-bis(4-trifluoromethylbenzylidene)-4-piperidone in 5 mL of tetrahydrofuran solution, add 0.02 g of 5 % tetrabutylammonium bromide, stirred at 0-5°C for 15 minutes, added dropwise 1.5mmol of 4-nitrobenzoyl chloride solution, continued to stir for 2 hours, and determined the reaction end point by thin layer chromatography (TLC) analysis. Suction filtration, add 10 mL of potassium carbonate solution with a mass fraction of 10% to the residue, stir at room temperature for 2 h, collect the precipitate, and recrystallize with methanol-chloroform mixed solvent to obtain N-(4-nitrobenzoyl)-3,5- Bis(4-trifluoromethylbenzylidene)-4-piperidone 0.44g, yield 78%.

[0035]

Embodiment 3

[0037] Synthesis of N-(4-methylbenzenesulfonyl)-3,5-bis(4-trifluoromethylbenzylidene)-4-piperidone c

[0038] Mix 2 mL of 25% NaOH solution with 1 mmol of 3,5-bis(4-trifluoromethylbenzylidene)-4-piperidone in 5 mL of 1,2-dichloroethane solution, add 0.01g of tetrabutylammonium chloride with a mass fraction of 5%, stirred at 0-5°C for 15min, added dropwise 1.5mmol of 4-methylbenzenesulfonyl chloride solution, continued to stir for 5h, and passed thin layer chromatography (TLC). Layer analysis to determine the reaction end point, with 2mol L -1 hydrochloric acid to adjust the pH to 1-4, collect the precipitate, and recrystallize with chloroform solvent to obtain N-(4-methylbenzenesulfonyl)-3,5-bis(4-trifluoromethylbenzylidene)-4 - piperidone 0.45g, yield is 79%.

[0039]

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Abstract

The invention relates to an antitumor 3,5-diphenylmethylene-4-piperidone derivative and a preparation method thereof, and belongs to the technical fields of antitumor drugs and preparation methods thereof. The preparation method comprises the following steps: performing a Claisen-Schmidt condensation reaction on a 4-piperidone derivative having antitumor activity and 4-trifluoromethyl through 4-piperidone hydrochloride to obtain an intermediate a; and reacting the intermediate a with an acylation or sulfonylation reagent to obtain N-R-3,5-di(4-trifluoromethyl benzylidene)-4-piperidone b-5. The 3,5-diphenylmethylene-4-piperidone derivative is novel in structure, has the advantage of combination of a plurality of molecular targets, and has multidrug resistance activity; and the genotoxicity of currently-used antitumor drugs can be avoided. Compared with normal cells, the derivative has higher antitumor activity to tumor cells, so that the derivative has a great application prospect in the field of antitumor drugs.

Description

technical field [0001] The invention relates to a 3,5-dibenzylidene-4-piperidone derivative used for antitumor and a preparation method thereof, and belongs to the technical field of antitumor drugs and the preparation method thereof. Background technique [0002] 3,5-Dibenzylidene-4-piperidinone derivatives are a class of cyclic α,β unsaturated ketones combined with β aminoketones. There are many α,β unsaturated ketone compounds, which are very important intermediates in organic synthesis, and are widely used in the fields of medicine, chemical industry and spices. Studies by Dimmock et al. have shown that many α and β unsaturated ketones show cytotoxicity and anti-tumor activity. The mode of action of these compounds is quite unique. They have significant affinity for sulfhydryl groups that do not exist in nucleic acids, but for amino groups that exist in nucleic acids. It has little or no affinity with hydroxyl, so it can avoid the genotoxicity of many anticancer drugs c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/68C07D213/89A61P35/00
CPCC07D213/68C07D213/89
Inventor 孙居锋王春华侯桂革李洪娟赵峰刘文帅
Owner BINZHOU MEDICAL COLLEGE
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