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Acetylpyrazine thiosemicarbazone metal chelating agent and preparation and application of metal complex of the acetylpyrazine thiosemicarbazone metal chelating agent

A technology of acetylpyrazine amino and diethyl semi-thiourea, which is applied in the field of medicine, can solve the problems that other metal-based compounds are useless and make significant progress, and achieve significant in vitro antitumor activity and good medicinal use. The effect of value, principle science

Inactive Publication Date: 2020-05-12
PINGDINGSHAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although platinum-based drugs such as cisplatin, carboplatin, and oxaliplatin are the main drugs used in the treatment of cancer with metal-based compounds, the research and development of other metal-based compounds has not made significant progress
There is no public report on the synthesis and application of 2-acetylpyrazine 4,4-diethylaminothiourea metal chelating agent and its metal complexes

Method used

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  • Acetylpyrazine thiosemicarbazone metal chelating agent and preparation and application of metal complex of the acetylpyrazine thiosemicarbazone metal chelating agent
  • Acetylpyrazine thiosemicarbazone metal chelating agent and preparation and application of metal complex of the acetylpyrazine thiosemicarbazone metal chelating agent
  • Acetylpyrazine thiosemicarbazone metal chelating agent and preparation and application of metal complex of the acetylpyrazine thiosemicarbazone metal chelating agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Synthesis of acetylpyrazine thiosemicarbazone metal chelating agent and its metal complexes.

[0028] The synthetic route is as follows:

[0029]

[0030] Concrete synthesis method is:

[0031] 1) Dissolve 1 mmol of 2-acetylpyrazine (0.122 g) in 20 ml of ethanol (concentration of solvent ethanol is 50 v / v%), stir at 80 °C for 15 min to obtain a solution, and dissolve the above solution one by one Add 1 mmol 4,4-diethylthiosemicarbazone (0.147 g) dropwise into 20 ml of ethanol (solvent ethanol concentration: 50 v / v%) solution, add 3 drops of concentrated hydrochloric acid, After reflux and stirring at 80°C for 24 hours, a light yellow precipitate was obtained. After filtering the light yellow precipitate obtained above, it was washed three times with absolute ethanol and ether, and after drying, the ligand 2-acetylpyrazine 4,4 - Diethylthiosemicarbazone hydrochloride. Light yellow crystals were obtained after recrystallization from ethanol;

[0032] The...

Embodiment 2

[0041] Example 2: Synthesis of acetylpyrazine thiosemicarbazone metal chelating agent and its metal complexes.

[0042] 2) Add 1 mmol of copper bromide (0.220g), gallium trichloride (0.174g) or ferric chloride (0.161g) in 20ml of methanol (concentration of solvent methanol is 60 v / v%) solution, drop Add 1 mmol of 2-acetylpyrazine 4,4-diethylthiosemicarbazone ligand in 20ml of ethanol (the concentration of solvent ethanol is 50 v / v%) solution, reflux and stir at 20 °C After 2 hours, filter the reacted solution into a 50 ml beaker, seal it with plastic wrap, prick 20 holes and volatilize at 4°C for several days to obtain crystals.

[0043] The obtained crystal is subjected to element analysis, mass spectrometry analysis and X-ray single crystal diffraction analysis, and the specific spectral characteristics are as follows:

[0044] Copper complexes:

[0045] (1) Elemental analysis:

[0046] Chemical formula: C 11 h 16 BrCuN 5 S. Elemental analysis results are: Calculated:...

experiment example 3

[0090] Experimental example 3: The antitumor activity experiment of the acetylpyrazine thiosemicarbazone metal chelating agent and its metal complex (prepared according to the method described in Example 1) and ligands of the present invention.

[0091] 1) Cell lines and cell culture

[0092] Tumor cell lines NCI-H460, A549, HepG2 and HeLa tumor cell lines were all from the American TypeCulture Collection ((Rockville MD, USA), and the cells were placed in an incubator with a volume concentration of 5% at 37 °C with 10% fetal bovine Serum and 100 μgmL -1 Streptomycin, 100 units per ml of penicillin in RPM-1640 medium culture.

[0093] 2) Cell growth inhibition assay (MTT method)

[0094] Note: The full name of MTT is 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2-H-tetrazoliumbromide, and the Chinese chemical name is 3-(4,5-dimethylthiazolyl-2)- 2,5-Diphenyl tetrazolium bromide, trade name: thiazolium blue, is a yellow dye.

[0095] After dissolving the acetylpyrazine thiosemi...

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Abstract

The invention discloses an acetylpyrazine thiosemicarbazone metal chelating agent as well as a preparation method and application of a metal complex of the acetylpyrazine thiosemicarbazone metal chelating agent. The synthesis method of the acetylpyrazine thiosemicarbazone metal chelating agent comprises the following steps: with 2-acetylpyrazine and 4, 4-diethyl thiosemicarbazone as raw materialsand an alcohol substance and hydrochloric acid as solvents, carrying out a reaction to generate a yellow precipitate, collecting the precipitate, and washing the precipitate to obtain a ligand; takingthe obtained ligand and a metal salt, and carrying out a reaction with the alcohol substance and acetonitrile as solvents, carrying out standing treatment on the reactant, and separating out and collecting the crystal, so as to obtain the acetylpyrazine thiosemicarbazone metal chelating agent and the metal complex thereof. The acetylpyrazine thiosemicarbazone metal chelating agent and the metal complex thereof have remarkable anti-tumor activity and can be used for tumor treatment.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to the preparation and application of an acetylpyrazine thiosemicarbazone metal chelating agent and a metal complex thereof. Background technique [0002] Although metal-based compounds are widely used in disease treatment, the lack of a clear distinction between therapeutic and toxic doses presents a major challenge. Barnett Rosenberg discovered cisplatin in 1960 and used it to treat cancer, which laid the foundation for the application of metal-based anticancer drugs. Although platinum-based drugs such as cisplatin, carboplatin, and oxaliplatin are the main drugs used to treat cancer with metal-based compounds, the research and development of other metal-based compounds has not made significant progress. With the development of structural informatics, a series of other forms of metal-based compounds and non-classical platinum complexes that are different from known d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/12C07F1/08C07F5/00A61P35/00
CPCA61P35/00C07B2200/13C07D241/12C07F1/005C07F5/003
Inventor 齐金旭夏西超王福安白现广韩晨露王典王瑞雅赵薇
Owner PINGDINGSHAN UNIVERSITY
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