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Platinum complex mixed with 2-methyl-8-hydroxyquinoline and tropolone and its preparation method and application

A technology of hydroxyquinoline and methyl, which is applied in the field of medicine to achieve a significant effect of inhibiting activity

Active Publication Date: 2021-05-28
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there has been no introduction of tropolone and 2-methyl-8-hydroxyquinoline as ligands into platinum complexes to achieve highly selective inhibitory activity of the complexes on gastric cancer MGC80-3 cell line

Method used

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  • Platinum complex mixed with 2-methyl-8-hydroxyquinoline and tropolone and its preparation method and application
  • Platinum complex mixed with 2-methyl-8-hydroxyquinoline and tropolone and its preparation method and application
  • Platinum complex mixed with 2-methyl-8-hydroxyquinoline and tropolone and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Take 2-methyl-8-hydroxyquinoline (0.0079g, 0.05mmol), tropolone (0.0061g, 0.05mmol), dichlorobis(dimethylsulfoxide) platinum (Pt(DMSO) 2 Cl 2 , 0.0211g, 0.05mmol) into the polytetrafluoroethylene liner, then add 5mL mixed solvent (composed of methanol and ethanol in a volume ratio of 1.5:1), stir to dissolve, then adjust the pH of the system with triethylamine= 9.45, then put the liner in the hydrothermal reaction kettle, seal it, then transfer the reaction kettle to an oven and heat it to 60°C for 72 hours of constant temperature reaction, take it out, and slowly cool it to room temperature, orange-red blocky crystals are precipitated, collect the crystals, Washed with ethanol and dried to obtain an orange-red solid product (yield 30%).

[0020] The product obtained in this embodiment was analyzed by elemental analysis, infrared spectrum, mass spectrum and X-ray single crystal diffraction, and the specific data are as follows:

[0021] (1) Elemental analysis, Anal.El...

Embodiment 2

[0038] Repeat Example 1, the difference is:

[0039] 1) In the composition of the mixed solvent, the volume ratio of methanol and ethanol is 4:1;

[0040] 2) adjust the pH of the resulting solution with ammonia water to 9.58;

[0041] 3) The reaction is carried out at 75°C.

[0042] After the reaction was completed, it was slowly cooled to room temperature, and orange-red blocky crystals were precipitated, with a yield of 13%.

[0043] Elemental analysis, infrared spectrum, mass spectrum and X-ray single crystal diffraction analysis were carried out on the product obtained in this example, and it was determined that the obtained orange-red solid product was the target product 2-methyl-8-hydroxyquinoline and tropolone mixed platinum complex.

Embodiment 3

[0045] Repeat Example 1, the difference is:

[0046] 1) In the composition of the mixed solvent, the volume ratio of methanol and ethanol is 1:1, and the total amount of the mixed solvent is changed to 10mL;

[0047] 2) adjust the pH of the resulting solution to 10.0 with 5w / w% sodium hydroxide solution;

[0048] 3) The reaction is carried out at 50°C.

[0049] After the reaction was completed, it was slowly cooled to room temperature, and orange-red block crystals were precipitated, with a yield of 16%.

[0050] Elemental analysis, infrared spectrum, mass spectrum and X-ray single crystal diffraction analysis were carried out on the product obtained in this example, and it was determined that the obtained orange-red solid product was the target product 2-methyl-8-hydroxyquinoline and tropolone mixed platinum complex.

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Abstract

The invention discloses a platinum complex mixed with 2-methyl-8-hydroxyquinoline and tropolone, a preparation method and application thereof. The preparation method of this 2-methyl-8-hydroxyquinoline and tropolone mixed platinum complex is: take 2-methyl-8-hydroxyquinoline, tropolone and dichloro-bis(dimethylmethylene Sulfone) combined with platinum is placed in a mixed solvent, and after dissolving, the pH of the system is adjusted to be greater than or equal to 9, and the resulting mixed solution is reacted under heating conditions, and the reactant is cooled, and crystals are precipitated to obtain that product; wherein, the mixed solvent is methanol and ethanol Compositions. The applicant's test showed that the complex has significant growth inhibitory activity on gastric cancer MGC‑803 cell line, which is significantly stronger than cisplatin, and its IC 50 The value is only one-third of that of cisplatin, and its toxicity to normal human cells HL‑7702 is lower than that of cisplatin.

Description

technical field [0001] The invention relates to a platinum complex mixed with 2-methyl-8-hydroxyquinoline and tropolone, a preparation method and application thereof, and belongs to the technical field of medicine. Background technique [0002] Platinum drugs have always occupied an important position in clinical antitumor drugs, and they have a significant effect on many malignant solid tumors such as bladder cancer, colon cancer, and non-small cell lung cancer [Kelland L.The recurrence of platinum-based cancer chemotherapy[J ]. Nature Reviews Cancer, 2007, 7(8): 573-584; Fricker S P. Metal based drugs: from serendipity to design [J]. Dalton Transactions, 2007(43): 4903-4917.]. Among them, several inorganic platinum anticancer drugs represented by cisplatin have good curative effects on various cancer types (such as testicular cancer, uterine cancer, bladder cancer, lung cancer, prostate cancer, etc.). However, platinum drugs such as cisplatin have side effects such as low...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00A61K31/555A61P35/00
CPCA61P35/00C07B2200/13C07F15/0093
Inventor 陈自卢莫稀玉储波梁福沛刘东成梁宇宁
Owner GUANGXI NORMAL UNIV
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