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Aloe-emodin quaternary ammonium salt alkyl iodoacetates with multiple-related anti-cancer mechanism

An aloe-emodin and quaternary ammonium salt technology, which is applied in the preparation of organic compounds, organic chemistry, quinone preparation, etc., can solve problems such as inhibiting the activity of cancer cells, and achieve inhibition of glycolysis, high correlation, and high anticancer activity. Effect

Inactive Publication Date: 2016-09-07
FUZHOU UNIV
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Problems solved by technology

Disruption of cancer cells' mitochondrial energy pathway alone may not be enough to severely suppress cancer cell activity

Method used

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  • Aloe-emodin quaternary ammonium salt alkyl iodoacetates with multiple-related anti-cancer mechanism
  • Aloe-emodin quaternary ammonium salt alkyl iodoacetates with multiple-related anti-cancer mechanism

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Embodiment 1

[0023] The preparation method of the aloe-emodin quaternary ammonium salt iodoacetate with multiple association anti-cancer mechanism, the specific steps are:

[0024] 1) Synthesis of brominated aloe-emodin

[0025] Dissolve 5.1 mmol aloe-emodin in 150 mL CCl 4 , add 5 mL PBr at room temperature 3 (excessive), warming up to 65°C, stirring and reacting for 48 h under reflux; after the solvent was removed by rotary evaporation, the residue was purified by silica gel column chromatography (eluent V (CH 2 Cl 2 ): V (petroleum ether)=2:1) ​​to obtain orange solid brominated aloe-emodin; product characterization data are as follows:

[0026] Yield: 72.1%; Melting point: 72-73°C; 1 H NMR (400 MHz, CDCl3) δ: 12.09 (s, 1H, ArOH), 12.06 (s, 1H, ArOH), 7.89 (d, J =5.2H z , 1H, ArH), 7.88 (s, 1H, ArH), 7.73 (t, J =7.6H z , 1H, ArH), 7.36 (s, 1H, ArH), 7.35 (d, J =6.4H z , 1H, ArH), 4.51 (s,2H, ArCH 2 Br); ESI-MS m / z 331.1 (M-H) - ; HRMS m / z 330.9619, theoretical (M-H) - ...

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Abstract

The invention discloses aloe-emodin quaternary ammonium salt alkyl iodoacetates with the multiple-related anti-cancer mechanism and a preparation method thereof. The preparation method comprises the steps that firstly, aloe-emodin reacts with phosphorus tribromide to obtain brominated aloe-emodin; secondly, brominated aloe-emodin reacts with N-methyldi-n-octylamine to generate aloe-emodin quaternary ammonium salt; lastly, the aloe-emodin quaternary ammonium salt reacts with chloroacetyl chloride to generate iodine acetylation in the presence of sodium iodide to obtain aloe-emodin quaternary ammonium salt alkyl iodoacetates shown as a structural formula (please see the structural formula in the description). In-vitro cancer cell inhibition tests of aloe-emodin quaternary ammonium salt alkyl iodoacetates show that aloe-emodin quaternary ammonium salt alkyl iodoacetates has the good inhibitory activity on hematopoietic cells, is expected to be developed into anti-leukemia drugs and has the great application prospect.

Description

technical field [0001] The invention belongs to the field of preparation of anticancer drugs, in particular to an aloe-emodin quaternary ammonium iodoacetate with multiple associated anticancer mechanisms. Background technique [0002] There are many characteristics that distinguish cancer cells from normal cells. Anticancer drugs designed only for a single characteristic of cancer cells generally have insufficient anticancer activity. For example, lipophilic cations such as rhodamine are a class of anticancer drugs designed for the mitochondrial membrane potential of cancer cells to be higher than that of normal cells. Although they have high targeting, they basically do not have the anticancer activity of a single drug. However, it is difficult to achieve a good anti-cancer effect simply by using multiple characteristics of cancer cells that are not related to each other as drug design targets, because it is difficult for one drug molecule to act on multiple targets. Ther...

Claims

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Application Information

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IPC IPC(8): C07C225/24C07C221/00A61P35/00A61P35/02
CPCC07C46/00C07C221/00C07C225/24C07C50/34
Inventor 王文峰孔露瑶胡秀芳苗军卫朱莉耿慧娟苏培荣
Owner FUZHOU UNIV
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