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Fluorophenyl-substituted asymmetric piperidone compounds with antitumor activity and preparation method thereof

A technology of anti-tumor activity and piperidone, applied in anti-tumor drugs, active ingredients of heterocyclic compounds, organic chemistry, etc., can solve the problem of asymmetric molecular polarity, unclear influence of solubility and activity, and lack of system of structure-activity relationship Sexuality and other issues, to achieve the effect of avoiding genotoxicity, low toxicity, and mild reaction conditions

Inactive Publication Date: 2016-06-15
BINZHOU MEDICAL COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nevertheless, the 3,5-bis(arylene)-4-piperidone derivatives reported in the literature and synthesized by our research group in the previous period are all symmetrical derivatives. There are few reports on methyl)-4-piperidone derivatives, and the analysis of structure-activity relationship is not systematic. The influence of polarity, solubility and different substituents on the activity of asymmetric molecules is still unclear

Method used

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  • Fluorophenyl-substituted asymmetric piperidone compounds with antitumor activity and preparation method thereof
  • Fluorophenyl-substituted asymmetric piperidone compounds with antitumor activity and preparation method thereof
  • Fluorophenyl-substituted asymmetric piperidone compounds with antitumor activity and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Synthesis of 3-(2-fluorobenzylidene)-5-(2-methoxybenzylidene)-4-piperidone (A)

[0024] Mix 0.01 mol of N-methyl-4-piperidone with 0.01 mol of 2-fluorobenzaldehyde and 0.01 mol of 2-methoxybenzaldehyde in a solution of 25 mL of ethanol and water, add 10 mL of 20% hydroxide dropwise at room temperature Sodium solution, stirred at room temperature for 4 h, and the end point of the reaction was determined by thin-layer chromatography (TLC) analysis. After the reaction was completed, the precipitate was suction filtered, and the obtained precipitate was chromatographed on a 200-300 mesh silica gel column (eluent: petroleum ether / ethyl acetate = 3:1) to obtain a yellow powder, which is the inventive product 3-(2-fluorobenzylidene yl)-5-(2-methoxybenzylidene)-4-piperidone (A), 1.81 g, yield 54%.

[0025] Mp: 89~91℃. IR(cm-1): ν2943, 2773, 1742, 1675, 1617, 1459, 1243, 1174, 1108, 1028, 922, 751. 1 HNMR (300MHz, CDCl 3 )δ8.11(s,1H),7.90(s,1H),7.40-6.92(m,8H),3.88(s,3H),3.70...

Embodiment 2

[0027] Synthesis of 3-(2-fluorobenzylidene)-5-(4-methoxybenzylidene)-4-piperidone (B)

[0028] Mix 0.01mol of N-methyl-4-piperidone with 0.011mol of 2-fluorobenzaldehyde and 0.009mol of 4-methoxybenzaldehyde in a solution of 18mL of methanol and water, add dropwise 15mL of 10% hydroxide at room temperature Potassium solution was stirred at room temperature for 3 h, and the end point of the reaction was determined by thin-layer chromatography (TLC) thin-layer analysis. After the reaction, the precipitate was filtered with suction, and the obtained precipitate was chromatographed on a 200-300 mesh silica gel column (eluent: petroleum ether / ethyl acetate = 5:1) to obtain a bright yellow powder, which is the inventive product 3-(2-fluorophenylene oxide) Methyl)-5-(4-methoxybenzylidene)-4-piperidone (B), 1.92 g, yield 57%.

[0029] Mp: 127~129℃.IR(cm-1):ν2940,2779,1669,1603,1573,1507,1454,1302,1259,1165,1023,922,826,759.Elementalanalysis(%)calcd.forC 21 h 20 FNO 2 (337.38):C74....

Embodiment 3

[0031] Synthesis of 3-(2-fluorobenzylidene)-5-(3,4-dimethoxybenzylidene)-4-piperidone (C)

[0032]Mix 0.01mol of N-methyl-4-piperidone with 0.009mol of 2-fluorobenzaldehyde and 0.011mol of 3,4-dimethoxybenzaldehyde in a solution of 20mL of ethanol and water, add dropwise 15mL of 20 % sodium hydroxide solution, stirred and reacted at 45°C for 3.5h, and the end point of the reaction was determined by thin-layer chromatography (TLC) thin-layer analysis. After the reaction was completed, the precipitate was suction-filtered, and the resulting precipitate was chromatographed on a 300-400 mesh silica gel column (eluent: petroleum ether / ethyl acetate = 4:1) to obtain a yellow powder, which was the inventive product 3-(2-fluorobenzylidene Dimethoxy)-5-(3,4-dimethoxybenzylidene)-4-piperidone (C), 1.90 g, yield 52%.

[0033] Mp: 116~118℃.IR(cm-1):ν2934,2782,1668,1608,1508,1446,1255,1146,1021,922,810,764.Elementalanalysis(%)calcd.forC 22 h 22 FNO 3 (367.41):C71.92,H6.04,N3.81; Found:...

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Abstract

The invention relates to six o-fluorophenyl-substituted asymmetric piperidone compounds with antitumor activity and a preparation method thereof, and belongs to the technical field of antitumor drugs and preparation methods thereof. The preparation method is that N-methyl-4-piperidone, 2-fluorobenzaldehyde and another aromatic aldehyde are subjected to Claisen-Schmidt condensation reaction to obtain the inventive products A to F. The compound has good antitumor activity, can avoid genotoxicity of antitumor drugs currently used, and has little toxicity to normal cells. The preparation method is easy to operate, the reaction conditions are mild, and the synthesis yield is high, which is beneficial to its wide promotion in the field of antitumor.

Description

technical field [0001] The invention relates to a series of o-fluorophenyl substituted asymmetric piperidone compounds with antitumor activity and a preparation method thereof, and belongs to the technical field of antitumor drugs and preparation methods thereof. Background technique [0002] The 3,5-diarylmethylene-4-piperidone derivative is optimized from the structure of curcumin and belongs to curcumin analogues. The structure contains two α,β-unsaturated ketone structural units, which can be The non-existing sulfhydryl group shows a better affinity, but has a weak affinity for active groups such as amino groups and hydroxyl groups in nucleic acids, showing significant affinity selectivity and better anti-tumor activity, and has been favored by scholars. extensive attention [1] . As a cytotoxic anti-tumor compound, it has two advantages compared with clinical anti-tumor drugs: first, it can avoid the genotoxicity of current clinical chemotherapy drugs, and the mechanis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/68A61K31/45A61P35/00A61P35/02
CPCC07D213/68
Inventor 侯桂革孙居锋王春华陈琴李宁刘梅
Owner BINZHOU MEDICAL COLLEGE
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