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Copper complex based on biotin o-vanillin acylhydrazone derivative and synthesis method and application thereof

A technology of oxalyl hydrazone and copper complexes, which can be applied to copper organic compounds, 1/11 group organic compounds without C-metal bonds, drug combinations, etc. The effect of good proliferation inhibitory activity and good medicinal value

Inactive Publication Date: 2018-09-21
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current technical difficulty lies in the difficulty of crystallization due to the complex arrangement of multiple carbon atoms in the side chain of valeric acid in the biotin molecule, making it difficult to determine its exact structure

Method used

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  • Copper complex based on biotin o-vanillin acylhydrazone derivative and synthesis method and application thereof
  • Copper complex based on biotin o-vanillin acylhydrazone derivative and synthesis method and application thereof
  • Copper complex based on biotin o-vanillin acylhydrazone derivative and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1: The compound shown in formula (II) is the synthesis of biotin o-vanillin hydrazone ligand

[0033]

[0034]Weigh 2.58g of biotin hydrazide and 1.52g of o-vanillin into a container, add 150mL of ethanol, and reflux for 5h to obtain a yellow solid product with a yield of 78%.

[0035] NMR, mass spectrometry and infrared analysis are carried out to the product obtained in the present embodiment, and the obtained spectral data are respectively as follows:

[0036] 1 H NMR(400MHz,DMSO)δ11.57(s,0.62H),11.21(s,0.38H),10.89(s,0,62H),9.53(s,0.38H),8.34(s,0.38H), 8.27(s,0.62H),7.25–7.20(m,0.38H),7.09–7.05(m,0.62H),7.03–6.99(m,1H),6.87–6.77(m,1H),6.46(s, 1H),6.38(bs,1H),4.33–4.25(m,1H),4.18–4.10(m,1H),3.80(s,1.14H),3.79(s,1.86H),3.15–3.08(m, 1H),2.85–2.78(m,1H),2.63–2.55(m,1.86H),2.25–2.18(m,1.14H),1.73–1.27(m,6H).

[0037] ESI-MS m / z: [L-H] + , 392.15

[0038] IR(KBr,cm -1 ): 3791m, 3378s, 2928s, 1678s, 1452s, 1258s, 1149w, 1079w, 752m.

[0039] Therefore...

Embodiment 2

[0041] Embodiment 2: The compound shown in formula (II) is the synthesis of biotin o-vanillin hydrazone ligand

[0042] Example 1 was repeated, except that the reaction was carried out at 50° C. and the reaction time was 5 h. The yield was 67%.

[0043] The product obtained in this example was analyzed by NMR, mass spectrometry and infrared, and it was determined to be biotin-o-vanillyl hydrazone ligand.

Embodiment 3

[0044] Embodiment 3: copper complex [CuL(CH 3 OH)] NO 3 - ·H 2 Synthesis of O (hereinafter referred to as complex 1):

[0045] Weigh 0.1176g of biotin o-vanillin hydrazone ligand and dissolve it in 10mL of methanol, then add 0.0725g of copper nitrate trihydrate, and place it in a 70°C water bath with magnetic stirring for 2 hours to make the mixed solution uniform to obtain a dark green solution; After cooling the dark green solution, filter it, place the filtrate in a 50mL small beaker, seal 2-3 pinholes with a plastic wrap, and slowly evaporate the solvent at room temperature. After 8 days of evaporation, dark green flaky crystals are obtained. The crystals were washed three times with methanol, and then dried at 50° C. for 6 h to obtain dark green flaky crystals. Yield 34%.

[0046] The obtained dark green flaky crystals of the present embodiment are characterized:

[0047] 1) Crystal structure analysis:

[0048] Single crystal X-ray analysis was performed on the dar...

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Abstract

The invention discloses a copper complex based on a biotin o-vanillin acylhydrazone derivative and a synthetic method and application thereof. The copper complex is obtained by reaction of an acylhydrazone ligand obtained by reaction of biotin hydrazide and o-vanillin and bivalent copper salt in a solvent. By investigating the proliferation and inhibition activity of the complex to multiple humantumor cell strains and human normal cell strains, the applicant finds that the complex shows better proliferation and inhibition activity to T-24 and A-549, has lower toxicity to human normal cells HL-7702, has better potential medicinal value and is expected to be used for preparation of various anti-tumor drugs. The structural formula of the copper complex is as shown in the formula (I) in the description, wherein, the solvent is CH3OH or C2H5OH, and anion is NO3<-> or ClO4<->.

Description

technical field [0001] The invention relates to a copper complex, in particular to a copper complex based on a biotin o-vanillylhydrazone derivative, a synthesis method and an application thereof. Background technique [0002] Since cisplatin was used clinically as an anticancer drug in 1978, various platinum metal anticancer drugs have come out one after another. Compared with cisplatin, carboplatin and oxaliplatin have enhanced their water solubility and chemical stability to reduce the Platinum has poor solubility in clinical practice, difficulty entering cell tissue, and nephrotoxicity. However, due to the characteristics of no specific target or single target limited to DNA during treatment, this type of platinum metal drug has led to the real entry There are very few drug molecules that can act on cells; while killing cancer cells, it also causes great damage to normal cells and tissues. [0003] Biotin (ie, vitamin H) is a physiologically acceptable and harmless nutr...

Claims

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Application Information

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IPC IPC(8): C07F1/08C07D495/04A61K31/555A61P35/00
CPCA61P35/00C07B2200/07C07B2200/13C07D495/04C07F1/005
Inventor 黄富平洪朝国边贺东李海叶于青
Owner GUANGXI NORMAL UNIV
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