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N1,N8-disubstituent-triethyl tetramine copper (II) complex and its prepn process

A technology of triethylenetetramine and di-substitution, which is applied in the direction of copper organic compounds, medical preparations containing active ingredients, and pharmaceutical formulas. It can solve problems such as research difficulties, low content, and complex structures, and achieve a simple and easy synthesis method. line, easy purification, and high-yield results

Inactive Publication Date: 2007-06-06
长治学院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the characteristics of large molecular weight, low content, complex structure and easy denaturation of protein, it is very difficult to study. Therefore, it is of great significance to find new simple and effective methods to specifically recognize DNA sequences and achieve purposeful gene regulation.

Method used

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  • N1,N8-disubstituent-triethyl tetramine copper (II) complex and its prepn process
  • N1,N8-disubstituent-triethyl tetramine copper (II) complex and its prepn process
  • N1,N8-disubstituent-triethyl tetramine copper (II) complex and its prepn process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] N 1 , N 8 -Synthesis of bis(1-methyl-4-nitropyrrole-2-yl)triethyltetramine copper(II) complex

[0088] Under stirring, dissolve 10.02g (36.9mmol) N-methyl-2-trichloroacetyl-4-nitropyrrole in 60mL of DMF, and cool at 0°C for 20min; under stirring, dissolve 2.70g (18.5mmol) 20mL of triethylenetetramine in DMF was added dropwise to the above solution within 30min; after the dropwise addition, the reaction mixture was stirred at 0°C for 2h, then raised to room temperature and continued to stir for 2h. Stop the reaction, add 200mL of water to the mixture, precipitate a yellow precipitate, filter, wash the precipitate with THF 3 times, 10mL each time, recrystallize the resulting solid with hot THF, and dry in vacuo to obtain 5.84gN 1 , N 8 -Bis(1-methyl-4-nitropyrrole-2-yl)triethyltetramine yellow solid (structural formula is as follows), the yield is 77%.

[0089]

[0090] The obtained yellow solid was analyzed and characterized:

[0091] 1. The measured melting poin...

Embodiment 2

[0105] N 1 , N 8 -Synthesis of bis(1-ethyl-4-nitropyrrole-2-yl)triethyltetramine copper(II) complex

[0106] Under stirring, dissolve 10.86g (38.0mmol) N-ethyl-2-trichloroacetyl-4-nitropyrrole in 60mL of DMF, and cool at 0°C for 20min; under stirring, dissolve 2.77g (19.0 mmol) 20 mL of triethylenetetramine in DMF was added dropwise to the above solution within 30 min; after the dropwise addition, the reaction mixture was stirred at 0°C for 2 h, then raised to room temperature and continued to stir for 2 h. Stop the reaction, add 200mL of water to the mixture, precipitate a yellow precipitate, filter, wash the precipitate with THF 3 times, 10mL each time, recrystallize the resulting solid with hot THF, and dry in vacuo to obtain N 1 , N 8 - bis(1-ethyl-4-nitropyrrole-2-yl)triethyltetramine yellow solid.

[0107] 0.405g (0.846mmol) N 1 , N 8 -bis(1-ethyl-4-nitropyrrole-2-yl)triethylenetetramine was dissolved in 100mL of DMF to form a ligand solution; 0.1443g (0.846mmol) C...

Embodiment 3

[0109] N 1 , N 8 -Synthesis of bis(1-propyl-4-nitropyrrole-2-yl)triethyltetramine copper(II) complex

[0110] Under stirring, dissolve 11.56g (38.6mmol) N-propyl-2-trichloroacetyl-4-nitropyrrole in 60mL of DMF, and cool at 0°C for 20min; under stirring, dissolve 2.82g (19.3 mmol) 20 mL of triethylenetetramine in DMF was added dropwise to the above solution within 30 min; after the dropwise addition, the reaction mixture was stirred at 0°C for 2 h, then raised to room temperature and continued to stir for 2 h. Stop the reaction, add 200mL of water to the mixture, precipitate a yellow precipitate, filter, wash the precipitate with THF 3 times, 10mL each time, recrystallize the resulting solid with hot THF, and dry in vacuo to obtain N 1 , N 8 - bis(1-propyl-4-nitropyrrole-2-yl)triethyltetramine yellow solid.

[0111] 0.394g (0.778mmol) N 1 , N 8 -bis(1-propyl-4-nitropyrrole-2-yl)triethyltetramine was dissolved in 100mL of DMF to form a ligand solution; 0.1327g (0.778mmol) ...

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Abstract

The present invention relates to N1, N8-disubstitutent-triethyl tetramine copper (II) complex as one kind of small molecular polyamine metal complex. Research shows that N1, N8-disubstitutent-triethyl tetramine copper (II) complex may be combined with DNA at the major groove in the insertion mode, the DFT process confirms the action mode between the complex and DNA, gel electrophoresis process shows that the complex can incise DNA, and MTT process proves the cancer cell inhibiting effect of the complex, so that the complex may be used in developing effective chemical nuclease and high efficiency and low toxicity anticancer medicine.

Description

technical field [0001] The present invention relates to a copper (II) complex of symmetrical polyamines, in particular to a N 1 , N 8 - Disubstituted triethyltetraamine copper (II) complexes, the invention also relates to a process for the preparation of the complexes. Background technique [0002] Cancer is one of the major diseases that threaten human life. In today's diseases, the fatality rate of cancer accounts for about 25%, which shows its great harm. With the understanding of tumor molecular biology, remarkable achievements have been made in cancer chemotherapy, and many drugs have been used in clinical treatment. However, it has been found that the anticancer agents used generally have the disadvantage of low selectivity to tumor cells, and almost all anticancer drugs also kill normal cells while killing cancer cells. Therefore, improving the selectivity of anticancer drugs and developing anticancer drugs with high efficiency and low toxicity have become the focu...

Claims

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Application Information

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IPC IPC(8): C07F1/08A61K31/555A61K31/30A61P35/00
Inventor 周成勇张宝秀杨频
Owner 长治学院
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