Two rare earth coordination compounds constructed on the basis of 2-methyl-5,7-dibromo-8-hydroxyquinoline, preparation method and applications thereof,

A technology of rare earth complexes and hydroxyquinoline, applied in medical preparations containing active ingredients, pharmaceutical formulas, organic chemical methods, etc., can solve the problems of no anti-proliferation activity and achieve significant anti-proliferation effects

Inactive Publication Date: 2020-04-03
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-dibromo-8-hydroxyquinoline has no antiproliferative activity on various tumor cells (IC 50 >50uM), so far there is no evidence that 2-methyl-5,7-dibromo-8-hydroxyquinoline is used as a ligand to construct the lanthanide metals samarium and thulium so that the resulting complexes have significant tumor inhibitory activity to report

Method used

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  • Two rare earth coordination compounds constructed on the basis of 2-methyl-5,7-dibromo-8-hydroxyquinoline, preparation method and applications thereof,
  • Two rare earth coordination compounds constructed on the basis of 2-methyl-5,7-dibromo-8-hydroxyquinoline, preparation method and applications thereof,
  • Two rare earth coordination compounds constructed on the basis of 2-methyl-5,7-dibromo-8-hydroxyquinoline, preparation method and applications thereof,

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Complex 1 (ie complex [Sm(C 10 H 6 NOBr 2 ) 3 (H 2 O)]) Preparation

[0031] Add 0.1mmol (44mg) Sm(NO 3 ) 3 ·6H 2 O and 0.2mmol (64mg) of ligand 2-methyl-5,7-dibromo-8-hydroxyquinoline (also referred to as ligand HL in this application) were added to a Pyrex tube with a closed end of about 18 cm in length, and added 1.25mL by CHCl 3 And H 2 O composition of mixed solvent (CHCl 3 And H 2 The volume ratio of O is 4:1), add 2 drops of Et 3 N (the pH value of the system after stirring is 7.5), the Pyrex tube is evacuated and the other end is sealed. Put the sealed Pyrex tube into an oven at 80°C, react for 72 hours, take it out, and slowly cool to room temperature. It can be observed that yellow strips of crystals are deposited at the bottom of the Pyrex tube. Collect the crystals and dry. The yield was 68% (based on Sm(NO 3 ) 3 ·6H 2 O).

[0032] Characterize the product obtained in this example:

[0033] 1) Elemental analysis (%): experimental value: C, 32.98, H, 1....

Embodiment 2

[0056] Example 2: Preparation of Complex 1

[0057] Repeat Example 1, the difference is: the mixed solvent CHCl 3 And H 2 Change the volume ratio of O to 1:1, use Et 3 N adjusts the pH of the system to 8.0. The reaction is changed to 60°C and the reaction time is 60h.

[0058] As a result, yellow bar-shaped crystals were obtained. The yield is 67% (based on Sm(NO 3 ) 3 ·6H 2 O).

[0059] The product obtained in this example was subjected to elemental analysis, infrared analysis and single crystal diffraction analysis, and it was determined that the obtained yellow stripe crystals were the target product complex 1.

Embodiment 3

[0060] Example 3: Preparation of Complex 1

[0061] Repeat Example 1, the difference is: the mixed solvent CHCl 3 And H 2 Change the volume ratio of O to 2:1, use Et 3 N adjusts the pH of the system to 6.5, and the reaction is carried out at 100°C.

[0062] As a result, yellow bar-shaped crystals were obtained. Yield 63% (based on Sm(NO 3 ) 3 ·6H 2 O).

[0063] The product obtained in this example was subjected to elemental analysis, infrared analysis and single crystal diffraction analysis, and it was determined that the obtained yellow stripe crystals were the target product complex 1.

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Abstract

The invention discloses two rare earth coordination compounds constructed on the basis of 2-methyl-5,7-dibromo-8-hydroxyquinoline, a preparation method and applications thereof, wherein the two coordination compounds are respectively a coordination compound 1 or a coordination compound 2, the molecular formula of the coordination compound 1 is [Sm(C10H6NOBr2)3(H2O)], and the molecular formula of the coordination compound 2 is [Tm(C10H6NOBr2)3(H2O)]. The preparation method of the rare earth coordination compound comprises the following steps: taking 2-methyl-5,7-dibromo-8-hydroxyquinoline and asamarium nitrate hexahydrate or thulium nitrate hexahydrate, dissolving with a mixed solvent, adjusting the pH value of the obtained solution to 6.5-8.1, and reacting the obtained mixed solution under a heating condition to obtain a corresponding target product. Test results show that the two rare earth coordination compounds have remarkable anti-proliferation effect on SK-OV-3 cell strains, havesignificantly high inhibition activity compared with cis-platinum, and are expected to be developed into anti-tumor drugs.

Description

Technical field [0001] The present invention relates to rare earth complexes, in particular to a rare earth complex based on 2-methyl-5,7-dibromo-8-hydroxyquinoline, and a preparation method and application thereof. Background technique [0002] Since the discovery of the anti-tumor properties of cisplatin drugs, the research and development of metal drugs has been vigorously developed. Although they have important effects as anticancer drugs, these drugs have obvious side effects, and their inherent insufficient drug resistance has prompted researchers to develop new platinum and non-platinum compounds. This situation has triggered a series of studies on complexes characterized by metal ions. Among them, ruthenium compounds have more successful examples in clinical trials, and therefore have become the best representative of drug candidates. When constructing complexes, researchers in the field recognize that the use of biologically active ligands to participate in the construc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/30A61K31/555A61P35/00
CPCC07D215/30A61P35/00C07B2200/13
Inventor 邹华红白娟梁福沛
Owner GUANGXI NORMAL UNIV
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