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Rare earth complexes constructed based on 2-methyl-5, 7-dichloro-8-hydroxyquinoline as well as preparation method and applications of rare earth complexes

A rare earth complex, hydroxyquinoline technology, applied in medical preparations containing active ingredients, pharmaceutical formulations, organic chemical methods, etc., can solve the problem of no anti-proliferative activity, and achieve the effect of low liver cell toxicity

Inactive Publication Date: 2020-03-13
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Existing experiments have shown that 2-methyl-5,7-dichloro-8-hydroxyquinoline has no antiproliferative activity on various tumor cells (IC 50 >50uM), so far there is no evidence that 2-methyl-5,7-dichloro-8-hydroxyquinoline is used as a ligand to construct the lanthanide metal erbium and holmium so that the resulting complex has significant tumor inhibitory activity. to report

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  • Rare earth complexes constructed based on 2-methyl-5, 7-dichloro-8-hydroxyquinoline as well as preparation method and applications of rare earth complexes
  • Rare earth complexes constructed based on 2-methyl-5, 7-dichloro-8-hydroxyquinoline as well as preparation method and applications of rare earth complexes
  • Rare earth complexes constructed based on 2-methyl-5, 7-dichloro-8-hydroxyquinoline as well as preparation method and applications of rare earth complexes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: complex 1 (being complex [Er(ClQ) 3 (H 2 O)]) Preparation

[0026] 45mg (0.2mmol) ligand H-ClQ and 46mg (0.1mmol) Er (NO 3 ) 3 ·6H 2 Add O to a Pyrex tube with one end closed and about 18 cm long, add 1.25 mL of a mixed solvent composed of ethyl acetate and water (the volume ratio of ethyl acetate and water is 4:1), add 2 drops of Et 3 N (the pH value of the system after stirring evenly is 8.0), vacuumize the Pyrex tube, and seal the other end. Put the sealed Pyrex tube into an oven at 80°C, react for 72 hours, and slowly cool down to room temperature. Yellow strip crystals can be observed at the bottom of the Pyrex tube. Collect the crystals and dry them. The yield was 67.9% (as Er(NO 3 ) 3 ·6H 2 O calculation).

[0027] The product obtained in this embodiment is characterized:

[0028] 1) Elemental analysis (%) (C 30 h 20 Cl 6 ErN 3 o 4 ), experimental value: C, 41.43, H, 2.43, N, 4.80; theoretical value: C, 41.58, H, 2.33, N, 4.85.

[0029...

Embodiment 2

[0048] Embodiment 2: the preparation of complex 1

[0049] Repeat Example 1, the difference is: change the volume ratio of ethyl acetate and water in the mixed solvent to 3:1, use Et 3 N adjusted the pH of the system to 7.7, changed the reaction to 60° C., and the reaction time was 80 h.

[0050] As a result, yellow stripy crystals were obtained. Yield 62% (based on Er(NO 3 ) 3 ·6H 2 O).

[0051] Elemental analysis, infrared analysis and X-ray diffraction analysis were carried out on the product obtained in this example, and it was confirmed that the obtained yellow strip crystal was the target product complex 1.

Embodiment 3

[0052] Embodiment 3: the preparation of complex 1

[0053] Repeat Example 1, the difference is: change the volume ratio of ethyl acetate and water in the mixed solvent to 5:1, use Et 3 N adjusted the pH of the system to 8.2, changed the reaction to 100° C., and the reaction time was 36 hours.

[0054] As a result, yellow stripy crystals were obtained. Yield 65% (based on Er(NO 3 ) 3 ·6H 2 O).

[0055] Elemental analysis, infrared analysis and X-ray diffraction analysis were carried out on the product obtained in this example, and it was confirmed that the obtained yellow strip crystal was the target product complex 1.

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Abstract

The invention discloses two rare earth complexes constructed on the basis of 2-methyl-5, 7-dichloro-8-hydroxyquinoline as well as a preparation method and application of the rare earth complexes. Thetwo rare earth complexes are respectively marked as complex 1 and complex 2, the molecular formula of the complex 1 is [Er(ClQ)3(H2O)], the molecular formula of the complex 2 is [Ho(ClQ)3(H2O)], and ClQ is 2-methyl-5, 7-dichloro-8-hydroxyquinoline with hydroxyl hydrogen atoms removed and with a unit of negative charges. The preparation method of the rare earth complexes comprises the following steps: taking 2-methyl-5, 7-dichloro-8-hydroxyquinoline and erbium nitrate hexahydrate or holmium nitrate hexahydrate, dissolving with a mixed solvent, and reacting under the heating conditions at a pH value of 7.7-8.2, thereby obtaining the rare earth complexes. Test results of the applicant show that the two rare earth complexes have a remarkable anti-proliferation effect on various tumor cells, are low in toxicity to human normal hepatocytes, and are expected to be developed into anti-tumor drugs.

Description

technical field [0001] The invention relates to a rare earth complex, in particular to a rare earth complex constructed on the basis of 2-methyl-5,7-dichloro-8-hydroxyquinoline and a preparation method and application thereof. Background technique [0002] At present, tumor seems to be the second leading disease of human death, which seriously endangers the physical and mental health of the people. Common malignant tumors include lung cancer, cervical cancer, breast cancer, liver cancer, lymphoma, leukemia and other types. Clinically, platinum-based antineoplastic drugs are still one of the most important chemotherapeutic drugs for tumor treatment, accounting for more than 50% of clinical chemotherapeutic drug applications. The main target of this type of drug against cancer is double-stranded DNA, and the main mechanism of action is to interfere with the double-strand replication of DNA in tumor cells, thereby exerting the goal of restraining cell growth. Despite their si...

Claims

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Application Information

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IPC IPC(8): C07D215/28A61P35/00A61K31/555
CPCC07D215/28A61P35/00C07B2200/13
Inventor 邹华红梁福沛
Owner GUANGXI NORMAL UNIV