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Novel 3, 5-bis(aryl-methyne)-1-methylpiperidine-4-ketone compound as well as synthetic method and application thereof in preparation of anti-cancer medicines

A kind of ketone compound, base methine technology, applied in novel 3,5-bis(aryl methine)-1-methylpiperidin-4-one compound, its synthesis and its use as anticancer drug It can solve the problems of unstable curative effect, large toxic and side effects, mental torture of patients, etc., and achieve good anti-cancer activity, no toxic and side effects, and the effect of natural materials.

Active Publication Date: 2014-07-23
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, most of the anticancer drugs in clinical application have relatively large toxic and side effects, coupled with the unstable curative effect, which brings mental torture to the patients, and brings great pain to cancer patients during the treatment process.

Method used

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  • Novel 3, 5-bis(aryl-methyne)-1-methylpiperidine-4-ketone compound as well as synthetic method and application thereof in preparation of anti-cancer medicines
  • Novel 3, 5-bis(aryl-methyne)-1-methylpiperidine-4-ketone compound as well as synthetic method and application thereof in preparation of anti-cancer medicines
  • Novel 3, 5-bis(aryl-methyne)-1-methylpiperidine-4-ketone compound as well as synthetic method and application thereof in preparation of anti-cancer medicines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1: (A1)

[0039] 3,5-bis-(4-fluorophenylmethine)-1-n-propylpiperidin-4-one

[0040] 1 HNMR(300MHz,DMSO):0.77(t,J=7.5Hz,3H,CH 3 ),1.31-1.41(m,2H,CH 2 ),2.46-2.50(m,2H,CH 2 ),3.81(s,4H),7.61(d,J=8.4Hz,4H),7.63(s,2H,benzylidene),8.00(d,J=8.1Hz,4H).ESI-Ms,m / e354. 1[M+H] +

Embodiment 2

[0041] Example 2: (A2)

[0042] 3,5-bis-(2,4-difluorophenylmethine)-1-n-propylpiperidin-4-one

[0043] 1 HNMR(500MHz,DMSO):0.76(t,J=7.5Hz,3H),1.35(q,J=7.5Hz,2H),2.43(t,J=7.5Hz,2H),3.70(s,4H), 7.19-7.23(m,2H),7.38-7.43(m,2H),7.53-7.58(m,2H),7.63(s,2H). 13 CNMR(125MHz, DMSO):12.0,20.1,54.2,58.4,105.0,112.4,119.4,126.7,132.8,135.6,160.3,162.3,186.6. 19 FNMR(470MHz,DMSO):-107.0,-108.8

Embodiment 3

[0044] Example 3: (A3)

[0045] 3,5-bis-(3,4-difluorophenylmethine)-1-n-propylpiperidin-4-one

[0046] 1 HNMR(300MHz,DMSO):0.79(s,3H,CH 3 ),1.40(s,2H,CH 2 ),2.51(s,2H,CH 2 ),3.78(s,4H,2CH 2 ),7.39(s,3H),7.56-7.64(m,6H)

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Abstract

The invention provides a novel 3,5-bis(aryl-methyne)-1-substituted-4-piperidone compound as well as a synthetic method and application thereof in the preparation of anti-cancer medicines. The structural formula of the novel 3,5-bis(aryl-methyne)-1-substituted-4-piperidone compound is as shown in a formula (I), wherein R1 is selected from hydrogen, propyl, benzyl, 2-phenethyl, acetyl and ethyoxyl carbonyl, R2, R3 and R4 are respectively and independently selected from fluorine, chlorine, bromine, C1-C12 alkenyl, C1-C12 alkyl, C1-C12 alkoxy, C1-C12 carboxylic acids, C1-C12 carboxylic esters and amide to which the C1-C12 carboxylic acids are corresponding, and n is 0 or 1. The compound has good anticancer activity and no toxic or side effects, is simple in synthetic method and suitable for preparation of the anti-cancer medicines.

Description

technical field [0001] The present invention relates to a class of compounds with anticancer activity and their application and synthesis method, in particular to a class of novel 3,5-bis(arylmethine)-1-substituted-4-piperidone compounds, which are synthesized Methods and their use as anticancer agents. Background technique [0002] At present, the main treatment methods for cancer include surgery, radiotherapy and chemotherapy. Generally, the appropriate treatment method is selected according to the patient's condition. Surgery and radiotherapy are relatively harmful to the patient. However, most of the anticancer drugs currently used in clinical practice have relatively high toxicity and side effects, and the instability of curative effect brings mental torture to patients, and brings great pain to cancer patients during the treatment process. The development of high-efficiency, low-toxicity anticancer drugs is not only an indispensable work to conquer cancer, but also a...

Claims

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Application Information

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IPC IPC(8): C07D213/68A61P35/00
CPCC07D213/68
Inventor 宋森川陈江韩潘文龙宋化灿万一千
Owner SUN YAT SEN UNIV
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