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Piperidone derivatives with antitumor activity and preparation method thereof

A technology of anti-tumor activity and piperidone, applied in the field of N-methyl-3,5-dibenzylidene)-4-piperidone derivatives and their preparation, anti-tumor drugs and their preparation, can Solve the problems of unstable chemical structure, low bioavailability, and limited application, and achieve the effects of avoiding genotoxicity, simple preparation method, and clear targeting

Active Publication Date: 2018-04-10
BINZHOU MEDICAL COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to poor water solubility, unstable chemical structure, and low bioavailability, its further clinical application is limited.

Method used

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  • Piperidone derivatives with antitumor activity and preparation method thereof
  • Piperidone derivatives with antitumor activity and preparation method thereof
  • Piperidone derivatives with antitumor activity and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Synthesis of N-methyl-3,5-bis(3-aminobenzylidene)-4-piperidone

[0021] Mix 0.01mol of N-methyl-4-piperidone and 0.022mol of m-nitrobenzaldehyde in a solution of 20mL of methanol and water, add 20mL of 20% sodium hydroxide solution at room temperature, stir and react at room temperature for 12h, pass Thin layer chromatography (TLC) TLC analysis determined the reaction endpoint. The precipitate was suction filtered to obtain the intermediate as light yellow powder. Add the intermediate and 0.065mol of stannous chloride to 25mL of concentrated hydrochloric acid and stir for 6-8h, and determine the end point of the reaction through thin-layer chromatography (TLC) analysis, precipitate and suction filter, 10% sodium carbonate solution lotion, 15mL ethanol / Water (volume ratio 1:1) was recrystallized to obtain a yellow powder, namely N-methyl-3,5-bis(3-aminobenzylidene)-4-piperidone.

Embodiment 2

[0023] N-methyl-3,5-bis(3-(2,3-dihydroxybenzylideneamino)benzylidene)-4-piperidone (A)

[0024] Dissolve 0.001mol N-methyl-3,5-bis(3-aminobenzylidene)-4-piperidone and 0.003mol 2,3-dihydroxybenzaldehyde in 40mL of methanol, add 3 drops of formic acid , stirred at room temperature for 8 h, and determined the end point of the reaction by thin layer chromatography (TLC) analysis. The precipitate was suction filtered, washed with methanol, and dried under vacuum to obtain red powder N-methyl-3,5-bis(3-(2,3-dihydroxybenzylideneamino)benzylidene)-4-piperidone (A) 0.3133 g, yield 56%.

[0025] IR (cm -1 ):3253(br),1614(s),1573(s),1460(m),1363(m),1273(s),1209(s),1183(m),1028(w),939(w ),850(w),789(m),734(s),684(s),540(w). 1 H NMR(400MHz,DMSO,25℃,TMS,ppm):δ13.03(s,2H),9.26(s,2H),8.97(s,2H),7.69(s,2H),7.62-7.50(m ,4H),7.50-7.40(m,4H),7.13(d,J=8Hz,2H),6.98(d,J=8Hz,2H),6.81(t,J=8Hz,2H),3.82(s, 4H), 2.42(s,3H).13C NMR (100MHz, CDCl 3 ):186.27,164.75,149.25,148.42,145.63,135.85,134.47...

Embodiment 3

[0027] N-methyl-3,5-bis(3-(2,4-dihydroxybenzylideneamino)benzylidene)-4-piperidone (B)

[0028] Dissolve 0.001mol N-methyl-3,5-bis(3-aminobenzylidene)-4-piperidone and 0.0035mol 2,4-dihydroxybenzaldehyde in 45mL methanol, add 6 drops of formic acid , stirred at room temperature for 9 h, and determined the end point of the reaction by thin layer chromatography (TLC) analysis. The precipitate was suction filtered, washed with methanol, and dried in vacuo to obtain yellow powder N-methyl-3,5-bis(3-(2,4-dihydroxybenzylideneamino)benzylidene)-4-piperidone (B) 0.3025 g, yield 54%.

[0029] IR (cm -1 ):3144(br),1672(w),1607(s),1568(s),1509(w),1455(w),1329(w),1281(w),1208(s),1176(m ),1127(m),977(m),850(m),788(s),691(s),651(w),538(w). 1 H NMR(400MHz,DMSO,25℃,TMS,ppm):δ13.38(s,2H),10.50(s,2H),8.84(s,2H),7.66(s,2H),7.53(t,J =8Hz,2H),7.46(d,J=8Hz,4H),7.38(t,J=8Hz,4H),6.43(d,J=8Hz,2H),6.31(s,2H),3.78(s, 4H),2.40(s,3H). 13C NMR (100MHz, CDCl 3 ): δ186.38, 163.44, 162.95, 162.66, 148...

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Abstract

The invention relates to four N-methyl-3,5-bis(3-(2-hydroxybenzylidene amino)benzylidene)-4-piperidone derivatives with antitumor activity and a preparation method thereof, and belongs to the technical field of antitumor drugs and preparation methods thereof.According to the preparation method of the derivatives, N-methyl-3,5-bis(3-aminobenzylidene)-4-piperidone and hydroxybenzaldehyde series compounds are subjected to a Schiff-base condensation reaction to obtain the products A-D.The derivatives are good in antitumor activity, can avoid the genotoxicity of antitumor drugs used at present and are definite in targeting.The preparation method is easy and convenient to implement, reaction conditions are mild, the synthesis yield is high, and thus the preparation method can be widely popularized in the antitumor field easily.

Description

technical field [0001] The invention relates to four kinds of N-methyl-3,5-bis(3-(2-hydroxybenzylideneamino)benzylidene)-4-piperidone derivatives with antitumor activity and their preparation methods The invention belongs to the technical field of antitumor drugs and preparation methods thereof. Background technique [0002] Curcumin has anti-inflammatory, anti-oxidation, anti-tumor, anti-atherosclerosis, anti-aging effects. However, its poor water solubility, unstable chemical structure, and low bioavailability limit its further clinical application. Furthermore, the structural modification of curcumin has become a research hotspot. 3,5-diaryl methylene-4-piperidinone derivatives are one of the currently studied curcumin derivatives. Because it has two α,β-unsaturated units, it can form two consecutive alkylations for sulfhydryl groups (which do not exist in nucleic acids), but have little or no affinity for amino and hydroxyl groups (in nucleic acids), namely It shows ...

Claims

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Application Information

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