Copper(ii) complexes using 9-aldehyde-10-pyrimanthracene hydrazone as ligands and their synthesis and application

A synthetic method and compound technology, applied in the field of medicine, can solve problems such as insignificant activity

Active Publication Date: 2021-05-14
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no significant biological activity obtained by using 9-formyl-10-(4',6'-dimethylpyrimidine) anthracene hydrazone as a ligand to coordinate with transition metal ion-copper(II) Related Reports on Binuclear Copper(II) Complexes

Method used

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  • Copper(ii) complexes using 9-aldehyde-10-pyrimanthracene hydrazone as ligands and their synthesis and application
  • Copper(ii) complexes using 9-aldehyde-10-pyrimanthracene hydrazone as ligands and their synthesis and application
  • Copper(ii) complexes using 9-aldehyde-10-pyrimanthracene hydrazone as ligands and their synthesis and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021]Example 1: Preparation of the compound (i.e., 9-aldehyde-10- (4 ', 6'-dimethylpyrimidine) 腙, hereinafter referred to as the ligand)

[0022]1) Take 5.0 mmol of 9,10-anthrafaldehyde and 6.5 mmol of 2-hydrazine-4,6-dimethylpyrimidine dissolved in 100 mL of methanol, and refluxed under 65 ° C and followed by TLC tracking. Complete (approximately 8 h), stopped the reaction, and the reaction liquid was filtered, the resulting solid was dried in vacuo to dry 10 h, resulting in a mixed product, yield 85%;

[0023]2) Elution of the resulting mixed product by silica gel column, mixed cleansing released by petroleum ether and dichloromethane eluting eluting eluting eluting, at the same time Monitoring, the eluent containing the target product was collected, concentrated, dried to give a yellow solid product, and the yield was 65%.

[0024]Infrared spectroscopy, elemental analysis, electrospray mass spectrometry, respectively, the yellow solid product obtained in this example,1H Nuclear magnetic ...

Embodiment 2

[0032]Example 2: Preparation of the compound of formula (II)

[0033]1) Take 5.0 mmol of 9,10-anthrafaldehyde and 5.0 mmol of 2-hydrazine-4,6-dimethylpyrimidine dissolved in 100 mL of methanol, and reflow under 65 ° C, followed by TLC tracking detection to the reaction Complete (approximately 6 h), the reaction was stopped, and the reaction liquid was filtered, the resulting solid was dried in vacuo to dry 10 h, resulting in a mixed product, yield 75%;

[0034]2) Elution of the resulting mixed product by silica gel column, mixed washing removal (petroleum ether, and dichloromethane) eluted, and trace at the same time Monitoring, the eluent containing the target product was collected, concentrated, dried to give a yellow solid product, and the yield was 45%.

[0035]Infrared spectroscopy, elemental analysis, electrospray mass spectrometry, respectively, the yellow solid product obtained in this example,1H Nuclear magnetic resonance spectrum and13C N-N-magnetic resonance spectrum identificatio...

Embodiment 3

[0036]Example 3: Preparation of the compound of formula (II)

[0037]1) Take 5.0 mmol of 9,10-anthraflicaldehyde and 7.0 mmol of 2-hydrazine-4,6-dimethylpyrimidine in 100 ml of ethanol, and reflow under conditions of 78 ° C, and track the reaction with TLC Complete (approximately 7 hours), the reaction was stopped, and the reaction liquid was filtered, the resulting solid was dried in vacuo to dry the mixed product, and the yield was 65%;

[0038]2) Elution of the resulting mixed product by silica gel column, mixed washing removal (petroleum ether, and dichloromethane) eluted by petroleum ether and dichloromethane, while taking a thin layer chromatography Monitoring, eluent containing the target product was collected, concentrated, dried to give a yellow solid product, 50% yield.

[0039]Infrared spectroscopy, elemental analysis, electrospray mass spectrometry, respectively, the yellow solid product obtained in this example,1H Nuclear magnetic resonance spectrum and13C N-N-magnetic resonance...

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Abstract

The invention discloses a copper (II) complex with 9-formyl-10-pyrimanthracene as a ligand, a synthesis method and an application thereof. The synthesis method of the copper complex is as follows: react 9-formyl-10-(4',6'-dimethylpyrimidine) anthracene and copper chloride under heating conditions in a polar solvent to obtain . The applicant's test results show that the complex has a significant anti-proliferation effect on various tumor cell lines, its activity is significantly improved compared with the ligand, and its activity is also significantly higher than that of cisplatin, and it is expected to be developed into an anti-tumor drug. Wherein, the structure of the copper (II) complex and 9-formyl-10-(4',6'-dimethylpyrimidine) anthracene hydrazone as ligand Respectively as shown in following formula (I) and formula (II):

Description

Technical field[0001]The present invention relates to copper (II) complexes and synthesis methods and synthesis methods and applications thereof in 9-aldehyde-10-congenic hunter, belong to the field of medical technology.Background technique[0002]Anthracecyclo anticancer drugs generally refer to a series of natural antitumor antibiotics based on anthraquinone, such as flexorubicin, doxorubicin, Mitoxantrone Wait. Such anti-tumor antibiotics have been successfully applied to clinical anti-tumor treatment, significant effects, and also occupy an important status in co-chemotherapy, such as CEF, AC and CAF, especially for leukemia, breast cancer, ovarian cancer, lung cancer and other efficacy. Significant.[0003]When constructing a complex, researchers are recognized by the use of biologically active ligands to construct an effective method of achieving synthetic multi-function compounds, such that the target product can be constructed to coordinate between metal centers and ligands. ef...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F1/08A61K31/30A61P35/00
CPCA61P35/00C07F1/08
Inventor 梁宏刘延成陈振锋刘瑞雪伍颖舒杜小倩
Owner GUANGXI NORMAL UNIV
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