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Ionic metal coordination compounds taking 9-aldehyde-10-pyrimidine anthracene hydrazone as ligand, synthesis method and applications thereof

A synthesis method and compound technology, applied in the field of medicine, can solve problems such as difficulty in effectively reducing liver and kidney toxicity, and achieve the effects of significant proliferation inhibitory activity, high activity, good biological affinity and compatibility

Active Publication Date: 2020-04-03
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the toxicity and side effects of platinum drugs are also significant, and it is difficult to effectively reduce liver and kidney toxicity

Method used

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  • Ionic metal coordination compounds taking 9-aldehyde-10-pyrimidine anthracene hydrazone as ligand, synthesis method and applications thereof
  • Ionic metal coordination compounds taking 9-aldehyde-10-pyrimidine anthracene hydrazone as ligand, synthesis method and applications thereof
  • Ionic metal coordination compounds taking 9-aldehyde-10-pyrimidine anthracene hydrazone as ligand, synthesis method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: Preparation of the compound shown in formula (II) (i.e. 9-formyl-10-(4',6'-dimethylpyrimidine) anthrahydrazone, hereinafter also referred to as ligand)

[0025] 1) Dissolve 5.0mmol of 9,10-anthracenedicarbaldehyde and 6.5mmol of 2-hydrazino-4,6-dimethylpyrimidine in 100mL of methanol, reflux at 65°C, and track and detect the reaction with TLC Complete (about 8h), stop the reaction, filter the reaction solution while it is hot, and dry the obtained solid in vacuum for 10h to obtain a mixed product with a yield of 85%;

[0026] 2) The resulting mixed product is eluted by silica gel column chromatography with a mixed eluent composed of petroleum ether and dichloromethane (volume ratio of petroleum ether and dichloromethane is 1:3), while tracking with thin layer chromatography Monitor, collect the eluate containing the target product, concentrate and dry it to obtain a yellow solid product with a yield of 65%.

[0027] Infrared spectrum, elemental analysis, ...

Embodiment 2

[0035]Embodiment 2: the preparation of compound shown in formula (II)

[0036] Example 1 was repeated, except that in step 2), a mixed eluent composed of petroleum ether and dichloromethane in a volume ratio of 1:1 was used for elution.

[0037] As a result, a yellow solid product was obtained with a yield of 30%.

[0038] Infrared spectrum, electrospray mass spectrometry, elemental analysis, 1 H NMR spectrum and 13 C nuclear magnetic resonance spectrum identification, determined to be the compound shown in formula (II).

Embodiment 3

[0039] Embodiment 3: the preparation of compound shown in formula (II)

[0040] Repeat Example 1, the difference is:

[0041] In step 1), ethanol is replaced with methanol, and the reaction is carried out at 80° C.;

[0042] In step 2), a mixed eluent composed of petroleum ether and dichloromethane at a volume ratio of 1:5 was used for elution.

[0043] As a result, a yellow solid product was obtained with a yield of 45%.

[0044] Infrared spectrum, electrospray mass spectrometry, elemental analysis, 1 H NMR spectrum and 13 C nuclear magnetic resonance spectrum identification, determined to be the compound shown in formula (II).

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PUM

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Abstract

The invention discloses two ionic metal coordination compounds taking 9-aldehyde-10-pyrimidine anthracene hydrazone as a ligand, a synthesis method and applications thereof. The synthesis method comprises the following steps: carrying out a reaction on 9-aldehyde 10-(4',6'-dimethylpyrimidine) anthracene hydrazone and rhodium trichloride hydrate or iridium trichloride hydrate in a polar solvent under a heating condition to obtaining the ionic metal coordination compounds. The ionic metal coordination compounds disclosed by the invention have ionic type structures, and have low toxicity to humannormal hepatocytes and high inhibition activity to tumor cell strains, wherein especially the rhodium coordination compound has significant proliferation inhibition activity to human bladder cancer cells T-24 and human lung cancer cells NCI-H460, and has significantly high activity compared with cis-platinum, so that the rhodium coordination compound is expected to be developed into antitumor drugs.

Description

technical field [0001] The invention relates to an ionic metal complex with 9-formyl-10-pyrimanthracene hydrazone as a ligand, a synthesis method and application thereof, and belongs to the technical field of medicine. Background technique [0002] Among the commonly used anticancer chemotherapeutic drugs, anthracyclines occupy an important position and have been successfully used for decades with remarkable curative effects. However, anthracyclines also have significant disadvantages and deficiencies, such as severe cardiotoxicity. Therefore, it is necessary to further develop new anthracycline derivative anti-tumor compounds based on the anthracycline structure. Among them, it is of great significance to effectively reduce its cardiotoxicity and other side effects. [0003] Anthracycline anticancer drugs, such as daunorubicin, doxorubicin, etc., all have a characteristic anthraquinone structure; and the anthraquinone structure can generate active oxygen free radicals in ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C07D239/42A61K31/282A61P35/00
CPCA61P35/00C07D239/42C07F15/0033C07F15/0073
Inventor 刘延成梁宏陈振锋刘瑞雪伍颖舒韩红华
Owner GUANGXI NORMAL UNIV