Aloe-emodin biquaternary ammonium salt with water solubility and anticancer activity and preparation thereof

A technology of aloe-emodin and diquaternary ammonium salt, which is applied in the field of preparation of quaternary ammonium salt anticancer drugs, can solve the problems of cancer cell apoptosis, and achieve the effect of simple synthesis steps, easy transport, and good inhibitory effect

Inactive Publication Date: 2016-03-16
FUZHOU UNIV
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  • Abstract
  • Description
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Problems solved by technology

Mitochondria are the main organelles that execute the apoptosis program, but the inner membrane of mitochondria is highly fat-soluble, and dr

Method used

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  • Aloe-emodin biquaternary ammonium salt with water solubility and anticancer activity and preparation thereof
  • Aloe-emodin biquaternary ammonium salt with water solubility and anticancer activity and preparation thereof
  • Aloe-emodin biquaternary ammonium salt with water solubility and anticancer activity and preparation thereof

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Embodiment 1

[0022] A preparation method of aloe-emodin diquaternary ammonium salt with water solubility and anticancer activity, the specific steps are:

[0023] (1) Synthesis of brominated aloe-emodin

[0024] 1.38g aloe-emodin (5.11mmol) with 150mLCCl 4 Dissolve in a 250mL three-neck flask, add 5mLPBr 3 (excessive) and then reflux and stir for 48 hours; after cooling, the solvent was removed by rotary evaporation, and the solid residue was eluted by silica gel column chromatography to obtain 1.23g of orange solid, namely brominated aloe-emodin, the eluent was dichloromethane / petroleum ether=2 : 1 (v / v); product characterization data are as follows: yield is 72.1%; m.p.72-73 ℃; 1 HNMR (400MH z , CDCl 3 )δ:12.09(s,1H,Ar-OH),12.06(s,1H,Ar-OH),7.89(d, J =5.2H z ,1H,Ar-H),7.88(s,1H,Ar-H),7.73(t, J =7.6H z ,J=8.4H z ,1H,Ar-H),7.36(s,1H,Ar-H),7.35(d, J =6.4H z ,1H,Ar-H),4.51(s,2H,ArCH 2 Br); ESI-MSm / z331.1(M-H) - ;HRMS(ESI - ):calcdforC 15 h 8 BrNO 4 [M-H] - =330.9611;Found,3...

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Abstract

The present invention belongs to the field of preparation of the quaternary ammonium salt anticancer drugs, and in particular to aloe-emodin biquaternary ammonium salt with water solubility and anticancer activity and a preparation method thereof. Aloe-emodin quaternary ammonium salt is first obtained, then aloe-emodin quaternary ammonium salt dibenzyl bromide is prepared, and finally aloe-emodin biquaternary ammonium salt is prepared. The preparation method has the advantages of simpleness, little side reaction and high product purity. The obtained biquaternary ammonium salt has better ability to inhibit leukemic cells while maintaining water solubility. The compound with water solubility and anti-cancer activity is expected to be developed into anti-cancer drugs, and has good application prospects.

Description

technical field [0001] The invention belongs to the field of preparation of quaternary ammonium salt anticancer drugs, in particular to an aloe-emodin diquaternary ammonium salt with water solubility and anticancer activity and a preparation method thereof. Background technique [0002] Quaternary ammonium salt anticancer drugs have the function of targeting the mitochondria of cancer cells, because the mitochondrial membrane potential of cancer cells is generally higher than that of normal cells, so positively charged quaternary ammonium salt anticancer drugs are easily enriched in the mitochondrial matrix of cancer cells . Mitochondria are the main organelles that execute the apoptosis program, but the inner membrane of mitochondria is highly fat-soluble, and drugs with strong water solubility are usually difficult to pass through the inner membrane of mitochondria to induce apoptosis in cancer cells. There are many examples of drug molecules losing anticancer activity du...

Claims

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Application Information

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IPC IPC(8): C07C225/24C07C221/00A61P35/00
CPCC07C46/00C07C221/00C07C225/24C07C50/34
Inventor 王文峰胡秀芳苗军卫谢世波
Owner FUZHOU UNIV
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