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Copper (I) complex based on butanone and salicylaldehyde amino triazole Schiff base, and synthesis method thereof

A synthesis method and complex technology, applied to copper organic compounds, 1/11 group organic compounds without C-metal bonds, organic chemical methods, etc., can solve problems that have not been seen before, and achieve low cost and easy availability of raw materials , The effect of simple process

Active Publication Date: 2020-12-01
柳州工学院
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, although there are many literatures reporting in situ ligand reaction, there is no salicylaldehyde-3-amino-1,2,4-triazine The azole Schiff base (see formula (1)) reacts with the solvent butanone to generate 5,13-dimethyl-3,11-dihydro-5H-5,11-methylbenzo[g][1,2 ,4]Triazolo[1,5-c][1,3,5]oxadiazosin (abbreviated as HL, its structure is shown in formula (2)), and then a report on the formation of copper (I) complexes

Method used

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  • Copper (I) complex based on butanone and salicylaldehyde amino triazole Schiff base, and synthesis method thereof
  • Copper (I) complex based on butanone and salicylaldehyde amino triazole Schiff base, and synthesis method thereof
  • Copper (I) complex based on butanone and salicylaldehyde amino triazole Schiff base, and synthesis method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Complex [Cu(HL) 2 The in-situ synthesis method of Cl] comprises the steps:

[0031] (1) Weigh 9.4 mg (0.05 mmol) of salicylaldehyde acetal-3-amino-1,2,4-triazole Schiff base and 5.0 mg (0.05 mmol) of CuCl at one end about 19 cm long with an inner diameter of 1.0 cm Into the sealed glass tube, add 2.0 mL methyl ethyl ketone, oscillate to make it fully mixed; then place the other end of the glass tube under vacuum to seal;

[0032] (2) Put the above-mentioned sealed glass tube in an oven at 120°C for reaction, stop heating after 72 hours of reaction, and then cool down to room temperature at 10°C per hour to obtain colorless long strip crystals, namely [Cu(HL) 2 Cl] product with a yield of 41.2%.

[0033] see figure 1 , it can be seen from the figure that there is only one crystallographically independent Cu(I) ion in the smallest unit of the complex of Example 1. Each N atom on the body (HL) is coordinated to form a chemical formula [Cu(HL) 2 Cl] complexes. The sm...

Embodiment 2

[0035] Complex [Cu(HL) 2 The in-situ synthesis method of Br] replaces CuCl in Example 1 with CuBr 7.2 mg (0.05 mmol), and other conditions remain unchanged, and also obtains colorless long strip crystals, i.e. [Cu(HL) 2 Br] product, productive rate is 40.2%, and molecular structure sees figure 2 , the structure is the same as figure 1 The only difference is that Cl atoms are replaced by Br atoms.

Embodiment 3

[0037] Determination of the IC of the two complexes of the examples to some cell lines by MTT colorimetry 50 The values ​​are shown in Table 1, where HL-7702 is a normal human liver cell line, A549 is a human lung cancer cell line, T-24 is a human bladder cancer cell line, and MGC80-3 is a human gastric cancer cell line.

[0038] Table 1, the IC of the example complexes on different cell lines 50 Value (μM)

[0039]

[0040] The results in Table 1 show that the two complexes of the examples have certain antitumor activity.

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Abstract

The invention discloses a copper (I) complex based on butanone and salicylaldehyde amino triazole Schiff base, and a synthesis method thereof. The synthesis method comprises the following steps: (1) weighing 8-12 mg of salicylaldehyde-3-amino-1, 2, 4-triazole Schiff base and 4-6 mg of CuCl or 6-8 mg of CuBr into a glass tube with one end sealed, adding 1.0-3.0 mL of butanone, oscillating to fullymix, and sealing the other end of the glass tube under a vacuum condition; and (2) putting the sealed glass tube into a drying oven at 110-130 DEG C for reaction, stopping heating after the reaction is carried out for 60-80 hours, and then cooling to room temperature at 10 DEG C per hour to obtain a colorless strip-shaped crystal, namely the copper (I) complex product. The 5, 13-dimethyl-3, 11-dihydro-5H-5, 11-methylbenzo[g][1, 2, 4]triazolo[1, 5-c][1, 3, 5]oxadiazole is a novel polycyclic compound, can be used as an intermediate to be applied to the fields of medicines, pesticides and the like, and forms a complex with metal ions, so that the complex has relatively good antibacterial and anticancer activity and important potential application.

Description

technical field [0001] The present invention relates to a copper complex and its in-situ synthesis method, specifically a copper (I) complex based on butanone and salicylaldehyde-3-amino-1,2,4-triazole Schiff base and its synthesis method. Background technique [0002] The in situ synthesis technology that appeared in recent years is widely used in the fields of chemistry, chemical industry, materials and so on. In situ synthesis refers to the in situ generation of one or several new compounds in the reaction system through chemical reactions under certain conditions. Through in situ synthesis, compounds that are difficult to obtain by other synthetic methods can be obtained. [0003] Although there are many literatures reporting the in situ ligand reaction, there is no salicylaldehyde acetal-3-amino-1,2,4-triazole Schiff base (see (1) formula) and solvent butanone A reaction occurs to generate 5,13-dimethyl-3,11-dihydro-5H-5,11-methylbenzo[g][1,2,4]triazolo[1,5-c][1 ,3,...

Claims

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Application Information

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IPC IPC(8): C07F1/08A61P31/04A61P35/00
CPCC07F1/005A61P31/04A61P35/00C07B2200/13
Inventor 陈勇王雅洁蒋毅民
Owner 柳州工学院
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