Binuclear metal complex with 9-formyl-10-imidanthracene as ligand, its synthesis method and application

A synthesis method and compound technology, applied in the field of medicine, can solve problems such as the synthesis method and application of binuclear metal complexes that have not yet been seen

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

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Problems solved by technology

However, there are no related reports on binuclear metal complexes with 9-formyl-10-imidanthrylhydrazone as a ligand and their synthesis methods and applications.

Method used

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  • Binuclear metal complex with 9-formyl-10-imidanthracene as ligand, its synthesis method and application
  • Binuclear metal complex with 9-formyl-10-imidanthracene as ligand, its synthesis method and application
  • Binuclear metal complex with 9-formyl-10-imidanthracene as ligand, its synthesis method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Example 1: Synthesis of 9-formyl-10-imanthrenehydrazone-binuclear copper (II) complex (hereinafter also referred to as copper complex)

[0032] 0.15mmol of 9-formyl-10-imidanthracene and 0.20mmol Cu(Ac) 2 ·H 2 O was dissolved in a polar solvent composed of 10.0mL methanol and 8.0mL chloroform, and reacted at 50°C (reflux for condensation) for 4 hours. After the reaction, the solution was cooled to obtain a brown suspension, and a large amount of complex solids were formed; filtered and collected filter cake to obtain a brown powdery solid product. The product was recrystallized from methanol to obtain a brown square block single crystal with a yield of 50%.

[0033] The brown powdery solid product obtained above was characterized by infrared spectroscopy, elemental analysis and electrospray mass spectrometry, and the specific spectral characteristic data are as follows:

[0034] Infrared spectrum: (KBr,cm -1 ) 3332, 2925, 1661, 1618, 1432, 1390, 1286, 1050, 753, 601...

Embodiment 2

[0045] Embodiment 2: the synthesis of copper complex

[0046] 0.25mmol of 9-formyl-10-imidanthrene hydrazone and 0.25mmol Cu(Ac) 2 ·H 2 O was dissolved in a polar solvent composed of 5mL ethanol and 20mL dichloromethane, and reacted at 60°C (reflux for condensation) for 6 hours. After the reaction, the solution was cooled to obtain a brown suspension, filtered, and the filter cake was collected to obtain a brown solid powder. , yield 45%.

[0047] The product obtained in this example was analyzed by infrared spectroscopy, elemental analysis and electrospray mass spectrometry, and it was determined that the obtained brown solid powder was the copper complex of the target compound.

Embodiment 3

[0048] Embodiment 3: the synthesis of copper complex

[0049] 0.20mmol of 9-formyl-10-imidanthracene and 0.25mmol Cu(Ac) 2 ·H 2 O was dissolved in a polar solvent consisting of 10.0mL methanol and 10.0mL chloroform, and reacted at 60°C (reflux for condensation) for 6 hours. After the reaction, the solution was cooled to obtain a brown suspension, filtered, and the filter cake was collected to obtain a brown solid powder. , yield 40%.

[0050] The product obtained in this example was analyzed by infrared spectroscopy, elemental analysis and electrospray mass spectrometry, and it was determined that the obtained brown solid powder was the copper complex of the target compound.

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Abstract

The invention discloses three cases of binuclear metal complexes with 9-formyl-10-imanthrene hydrazone as ligands, their synthesis methods and applications. The synthetic method of the dinuclear metal complex with 9-formyl-10-imanthrone hydrazone as ligand is: get the acetate of 9-formyl-10-imanthrene hydrazone and copper, zinc or manganese in polar Reaction in a solvent to obtain the corresponding target compound. The applicant's test results show that these three metal complexes have significant anti-proliferation effects on various tumor cell lines, especially the manganese complexes, whose activity is significantly improved compared with the ligands, and the activity is also significantly higher than that of the cis Platinum is expected to be developed into an antitumor drug.

Description

technical field [0001] The invention relates to a binuclear metal complex with 9-formyl-10-imanthrene hydrazone as a ligand, a synthesis method and application thereof, and belongs to the technical field of medicine. Background technique [0002] Anthracycline anticancer drugs usually refer to a series of natural antitumor antibiotics and their derivatives based on anthraquinone, such as Daunorubicin, Doxorubicin, Mitoxantrone Wait. This kind of anti-tumor antibiotics has been successfully used in clinical anti-tumor therapy, and has a remarkable effect. At the same time, it also plays an important role in combined chemotherapy regimens such as CEF, AC, and CAF, especially for leukemia, breast cancer, ovarian cancer, and lung cancer. significantly. In recent years, new non-anthraquinone anthracycline anticancer drugs have been synthesized and successfully developed, such as Bisantrene (Bisantrene) is a typical example. The anthrazone side chain group of bisantrene is a sp...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F1/08C07F3/06C07F13/00A61P35/00
CPCA61P35/00C07B2200/13C07F1/005C07F3/003C07F13/005
Inventor 梁宏刘延成陈振锋刘瑞雪伍颖舒杨丽东
Owner GUANGXI NORMAL UNIV
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