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Antitumor 3,5-diphenylmethylene-4-piperidone derivative and preparation method thereof

A technology of dibenzylidene and trifluoromethylbenzylidene, which is applied in the field of antineoplastic drugs and their preparation, achieves great application prospects, avoids genotoxicity, and has the effect of novel structure

Active Publication Date: 2015-01-07
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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  • Antitumor 3,5-diphenylmethylene-4-piperidone derivative and preparation method thereof
  • Antitumor 3,5-diphenylmethylene-4-piperidone derivative and preparation method thereof
  • Antitumor 3,5-diphenylmethylene-4-piperidone derivative and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0033] Synthesis of 3,5-bis(4-trifluoromethylbenzylidene)-4-piperidinone a

[0034] Mix 0.005 mol of 4-piperidone hydrochloride and 0.01 mol of 4-trifluoromethylbenzaldehyde in 12.5 mL of glacial acetic acid, pass through dry HCl gas at room temperature for 60 min, stir for 8 h, pass through a thin The end point of the reaction was determined by thin-layer chromatography (TLC) analysis. 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%.

[0035]

Embodiment 2

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

[0038]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 Tetrabutylammonium bromide with a fraction of 5% was stirred at 0-5°C for 15 min, 1.5 mmol 4-nitrobenzoyl chloride solution was added dropwise, and stirring was continued for 2 h. The end point of the reaction was determined by layer analysis, suction filtration, the residue was added to 10 mL of potassium carbonate solution with a mass fraction of 10%, stirred at room temperature for 2 h, the precipitate was collected, and recrystallized with methanol-chloroform mixed solvent to obtain N-(4-nitrobenzene Formyl)-3,5-bis(4-trifluoromethylbenzylidene)-4-piperidone 0.44g, yield 78%.

[0039]

Embodiment 3

[0041] Synthesis of N-(4-methylbenzenesulfonyl)-3,5-bis(4-trifluoromethylbenzylidene)-4-piperidone c

[0042] 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 Mix in medium, add 0.01 g of tetrabutylammonium chloride with a mass fraction of 5%, stir for 15 min at 0-5°C, add 1.5 mmol of 4-methylbenzenesulfonyl chloride solution dropwise, continue stirring for 5 h, pass through a thin Thin-layer chromatography (TLC) was used to determine the end point of the reaction, and 2 mol 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%.

[0043]

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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. [0002] Background technique [0003] 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 antican...

Claims

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Application Information

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Patent Type & Authority Applications(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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