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Copper compound adopting 2-acetyl-3-ethyl pyrazine thiosemicarbazone as ligand as well as synthetic method and application thereof

A technology of ethylpyrazine thiosemicarbazide and copper compounds, applied in the field of synthesis of copper compounds, can solve problems such as no application yet, few compound reports, etc., achieve activity improvement, overcome drug resistance, excellent resistance The effect of glioma activity

Inactive Publication Date: 2018-11-30
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] After searching, there are few reports of compounds with this structure, and there is no information about its application in glioma activity

Method used

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  • Copper compound adopting 2-acetyl-3-ethyl pyrazine thiosemicarbazone as ligand as well as synthetic method and application thereof
  • Copper compound adopting 2-acetyl-3-ethyl pyrazine thiosemicarbazone as ligand as well as synthetic method and application thereof
  • Copper compound adopting 2-acetyl-3-ethyl pyrazine thiosemicarbazone as ligand as well as synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Synthesis of C1 copper compound

[0033] The specific synthesis method is:

[0034] (1) Dissolve 10 mmol of 2-acetyl-3-ethylpyrazine in 20 mL of methanol, stir at 60 ° C for 15 min, then add 20 mL, 10 mmol of methanol solution of thiosemicarbazine to the above solution dropwise, in After refluxing and stirring at 60°C for 12 hours, the mixture was cooled to room temperature and poured into a beaker to volatilize. The obtained pale yellow crystals were filtered and washed with methanol for 3 times to obtain the ligand (L1);

[0035] (2) will contain CuCl 2 ·2H 2 O (170.48 mg, 1 mmol) in 30 mL of acetonitrile solution was added dropwise to 10 mL of methanol solution containing 1 mmol of the above-mentioned L1 ligand, stirred at 65°C under reflux for 24 h, the reaction solution was filtered into a 50 mL beaker, and sealed with plastic wrap, Acupuncture 15 holes and volatilized for several days at room temperature to obtain a yellow-brown crystal (C1), whose s...

Embodiment 2

[0037] Example 2: Synthesis of C2 Copper Compounds

[0038] The specific synthesis method is:

[0039] (1) 10mmol of 2-acetyl-3-ethylpyrazine was dissolved in 20mL of methanol, stirred at 60°C for 15min, and then 20mL, 10mmol of 4-methylthiosemicarbazine methanol solution was added dropwise to the above solution , after the reaction was stirred at 60°C for 12 h, cooled to room temperature, poured into a beaker and volatilized, the light yellow crystals obtained above were filtered and washed with methanol for 3 times to obtain the ligand (L2);

[0040] (2) will contain CuBr 2 (223.35 mg, 1 mmol) 30 mL of acetonitrile solution was added dropwise to 10 mL of methanol solution containing 1 mmol of the above-mentioned L2 ligand, and stirred at 65°C under reflux for 24 h. After the reaction, the solution was filtered into a 50 mL beaker, sealed with plastic wrap, and needled. The 15 holes were volatilized for several days at room temperature to obtain yellow-brown crystals (C2), ...

Embodiment 3

[0042] Embodiment 3: the synthesis of C3 copper compound

[0043] The specific synthesis method is:

[0044] (1) Dissolve 10mmol of 2-acetyl-3-ethylpyrazine in 20mL of methanol, stir at 60°C for 15min, then add 20mL, 10mmol of 4-phenyl-3-thiosemicarbazide methanol solution dropwise into the above solution, reflux at 60°C and stir for 12 hours, then cool to room temperature and pour into a beaker for volatilization, filter the light yellow crystals obtained above and wash them with methanol three times to obtain the ligand (L3);

[0045] (2) will contain CuBr 2 (223.35 mg, 1 mmol) 30 mL of acetonitrile solution was added dropwise to 10 mL of methanol solution containing 1 mmol of the above-mentioned L3 ligand, stirred at reflux at 65°C for 24 hours, and the reaction solution was filtered into a 50 mL beaker, sealed with plastic wrap, and pricked with a needle 15 holes were volatilized at room temperature for several days to obtain yellow-brown crystals (C3), whose single crys...

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Abstract

The invention discloses a copper compound adopting 2-acetyl-3-ethyl pyrazine thiosemicarbazone as ligand as well as a synthetic method and application thereof. The synthetic method of the copper compound comprises the following steps: measuring 2-acetyl-3-ethyl pyrazine and thiosemicarbazide, reacting by using methanol as a solvent, after the reaction, transferring into a beaker, volatilizing, crystallizing, obtaining ligand 2-acetyl-ethyl pyrazine thiosemicarbazone crystals, filtering the crystals, and washing the crystals by using methanol; enabling the ligand 2-acetyl-ethyl pyrazine thiosemicarbazone to react with CuCl2 or CuBr2 in the mixed solvent of acetonitrile and methanol, transferring the reactant into the beaker, standing, cooling, volatilizing and crystallizing, collecting thecrystals, and obtaining the target compound. By researching the in-vitro glioma resistance and drug-resistant strain activity of the synthesized copper compound, the result shows that the compound forms thiosemicarbazone ligand with the metal copper, the activity is greatly improved, the glioma resistant activity is excellent, and the drug resistance can be overcome to certain extent.

Description

technical field [0001] The invention relates to the synthesis of copper compounds, in particular to a copper compound using 2-acetyl-3-ethylpyrazine thiosemicarbazine as a ligand and a synthesis method and application thereof. Background technique [0002] Glioma is the primary intracranial malignant tumor with the highest incidence, accounting for about 46% of intracranial tumors. Existing treatment methods such as surgery, radiotherapy and chemotherapy have a cure rate of less than 30%. Currently, commonly used clinical drugs for brain tumor treatment are small molecule drugs, but they face many severe tests in the process of use. 1) The influence of the nature of the drug itself, many anti-infective or anti-tumor drugs are insoluble small molecule drugs, which brings difficulties to clinical administration, especially intravenous administration; 2) Drug resistance, whether it is the cause of infection Pathogens are also tumor cells that cause tumors. After continuous mul...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F1/08A61P35/00
CPCA61P35/00C07F1/005
Inventor 杨峰于萍王俊梁宏
Owner GUANGXI NORMAL UNIV
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