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Quinoline thiosemicarbazone-copper pyridine complex and preparation method and application thereof

A technology of quinoline thiosemicarbazide and copper complexes, which can be applied to copper organic compounds, chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, etc. Synthesis methods and applications of organic ligands and their copper complexes to achieve the effect of enhancing selectivity and diversity, and high anti-tumor cell proliferation activity

Active Publication Date: 2018-08-14
HENAN UNIV OF URBAN CONSTR
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the current research, there is no relevant report on the synthesis method and application of quinoline thiosemicarbazone-pyridine organic ligand and its copper complex

Method used

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  • Quinoline thiosemicarbazone-copper pyridine complex and preparation method and application thereof
  • Quinoline thiosemicarbazone-copper pyridine complex and preparation method and application thereof
  • Quinoline thiosemicarbazone-copper pyridine complex and preparation method and application thereof

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Experimental program
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Embodiment 1

[0028] The structural formula of quinoline thiosemicarbazone-pyridine ligand copper complex is as follows:

[0029] .

[0030] The preparation steps of quinoline thiosemicarbazone-pyridine ligand copper complex are as follows:

[0031] (1) Weigh 2-aminopyridine (7.6 g, 0.08 mol) into a single-necked flask, add carbon disulfide (9.6 mL, 0.16 mol), triethylamine (24 mL, 0.16 mol), heat and stir the mixture in a water bath until clear , stirred at room temperature for 24 h. Treatment: Take the mixture in the flask and filter, and after obtaining the filter residue, use a small amount of methanol to completely dissolve it to reach a hot saturated solution. Then, slowly add a small amount of saturated methanol solution containing a large amount of product into a large amount of ether solution, and the yellow product quickly reappears in the ether solution. Intermediate product A crystallized out. Yield: 53%.

[0032] (2) Weigh the obtained yellow product A (12 g) into a round...

Embodiment 2

[0038] The structural formula of quinoline thiosemicarbazone-pyridine ligand copper complex is as follows:

[0039] .

[0040] The preparation steps of quinoline thiosemicarbazone-pyridine ligand copper complex are as follows:

[0041] The preparation steps of quinoline thiosemicarbazone-pyridine organic ligand are as follows:

[0042] (1) Weigh 2-aminopyridine (7.6 g, 0.08 mol) into a single-necked flask, add carbon disulfide (4.8 mL, 0.08 mol), triethylamine (12 mL, 0.08 mol), heat and stir the mixture in a water bath until clear , stirred at room temperature for 12 h. Treatment: Take the mixture in the flask and filter, and after obtaining the filter residue, use a small amount of methanol to completely dissolve it to reach a hot saturated solution. Then, slowly add a small amount of saturated methanol solution containing a large amount of product into a large amount of ether solution, and the yellow product quickly reappears in the ether solution. Intermediate product...

Embodiment 3

[0048] The structural formula of quinoline thiosemicarbazone-pyridine ligand copper complex is as follows:

[0049] .

[0050] The preparation steps are as follows:

[0051] The preparation steps of quinoline thiosemicarbazone-pyridine organic ligand are as follows:

[0052] (1) Weigh 2-aminopyridine (7.6 g, 0.08 mol) into a single-necked flask, add carbon disulfide (7.2 mL, 0.12 mol), triethylamine (18 mL, 0.12 mol), heat and stir the mixture in a water bath until clear , stirred at room temperature for 18 h. Treatment: Take the mixture in the flask and filter, and add the filter residue to ether solution, stir and wash at room temperature for 10-20 min, filter, and dry the filter residue in air to obtain intermediate product A. Yield: 85%.

[0053] (2) Weigh the obtained yellow product A (10 g) into a round bottom flask, add methanol (35 mL) and methyl iodide (3 mL), and stir at room temperature for 1.5 h to obtain a reddish-brown reaction solution. Treatment: Slowly ...

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Abstract

The invention provides a quinoline thiosemicarbazone-copper pyridine complex and a preparation method and application thereof. The structural formula of the copper complex is shown in the formula I orthe formula II which is shown in the description. Thiosemicarbazide, quinoline and pyridine groups are combined, a new compound has multiple advantages of thiosemicarbazide, quinoline and pyridine and has coordination sites formed by drug effect groups of different types, and the coordination selectivity and diversity of the compound are improved. A ligand is bonded with metal ions to form the complex, and the double advantages of a metal center and an organic compound are presented. Through diversified coordination modes of the ligand and the formed complex with a specific structure, the specific biological activity is generated. The copper complex formed by human endogenous metal copper has the biological activity and expresses extremely high activity of resisting tumor cell proliferation.

Description

technical field [0001] The invention relates to the field of preparation of thiosemicarbazide-based compounds, in particular to a quinoline thiosemicarbazone-pyridine copper complex and its preparation method and application. Background technique [0002] Thiosemicarbazide derivatives and their metal complexes have good pharmacological and biological activities. Since thiosemicarbazides have the same coordination atoms as biological ligands such as amino acids, peptides, proteins, enzymes, and ribonucleic acids, they pass nitrogen, The coordination between sulfur atoms and metal ions is close to the biological environment, which has important application prospects. After the thiosemicarbazide derivative is coordinated with the transition metal ion to form a complex, the biological activity of the thiosemicarbazide-based complex can be further modified and enhanced. Quinoline compounds have high bioavailability, low toxicity, good environmental compatibility, and can be subj...

Claims

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Application Information

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IPC IPC(8): C07F9/6558C07F1/08A61P35/00
CPCA61P35/00C07F1/08C07F9/65583
Inventor 胡继勇廖春丽赵金安董召锋张军帅毛瑞娜谷珍珍
Owner HENAN UNIV OF URBAN CONSTR
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