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A kind of dihalogenated coumarin-platinum (ii) complex and its synthesis method and application

A technology of coumarin substitution and synthesis method, which is applied in the direction of platinum-based organic compounds, platinum-group organic compounds, and compounds containing elements of group 8/9/10/18 of the periodic table, etc., which can solve the toxic and side effects of platinum-based drugs, Poor water solubility, non-specific targeting, etc., to achieve superior in vitro anti-tumor activity and good inhibitory effect

Active Publication Date: 2020-05-15
YULIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, in order to solve the problems of toxic side effects, drug resistance, poor water solubility, and non-specific targeting of platinum-based drugs, researchers have tried many improvements, such as: glycosylation of ligands, halogenation, etc. Substitution, increase branching, etc. in order to improve the drug resistance, targeting, side effects, etc. of platinum-based drugs

Method used

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  • A kind of dihalogenated coumarin-platinum (ii) complex and its synthesis method and application
  • A kind of dihalogenated coumarin-platinum (ii) complex and its synthesis method and application
  • A kind of dihalogenated coumarin-platinum (ii) complex and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Accurately weigh 1.0 mmol of dichloro-bis(dimethylsulfoxide) platinum (II) and 1.0 mmol of ligand FFBC, dissolve dichloro-bis(dimethyl sulfoxide) platinum (II) Dissolve the ligand FFBC in 3 mL of methanol in 1 mL of dimethyl sulfoxide solution, then mix the two solutions and put them into a polytetrafluoroethylene reactor, react at 100 ° C for 48 hours, cool to room temperature, and precipitate The yellow granular solid was washed with distilled water, methanol and ether in turn, and the compound 1 was obtained after vacuum drying with a yield of 80.3%.

[0038] The resulting yellow granular crystals were identified:

[0039] (1) Infrared spectrum, its spectrogram is as follows Figure 4 Shown:

[0040] IR(KBr):3242,3039,1727,1590,1431,1378,1309,1241,1139,1095,969,737,677,442cm -1 .

[0041] (2) Proton NMR spectrogram, its spectrogram is as figure 1 shown.

[0042] 1 H NMR (600MHz, DMSO-d 6 )δ14.05(d,J=86.0Hz,1H),9.73(d,J=288.3Hz,1H),8.32-8.20(m,1H),7.97(ddd,J=1...

Embodiment 2

[0050] Accurately weigh 1.5 mmol of dichloro-bis(dimethylsulfoxide) platinum (II) and 1.0 mmol of ligand ClClBC, dissolve dichloro-bis(dimethyl sulfoxide) platinum (II) In 1 mL of dimethyl sulfoxide solution, the ligand ClClBC was dissolved in 4 mL of methanol, and then the two solutions were mixed and put into a polytetrafluoroethylene reactor, and reacted at 100 ° C for 24 hours, and the program was set at 10 ° C / The temperature was lowered at a rate of h to room temperature, and a solid was precipitated. The solid was washed with distilled water, methanol, and ether in sequence, and complex 2 was obtained after vacuum drying with a yield of 85.3%.

[0051] The obtained complex 2 is identified:

[0052] (1) Infrared spectrum, its spectrogram is as follows Figure 8 Shown:

[0053] IR(KBr):3225,1729,1564,1407,1152,1111,1024,992,764,737,548,434cm -1 .

[0054] (2) Proton NMR spectrogram, its spectrogram is as Figure 5 shown.

[0055] 1 H NMR (600MHz, DMSO-d 6 )δ14.0...

Embodiment 3

[0063] Accurately weigh the amount of the substance as 2.0mmol dichlorobis(dimethylsulfoxide)platinum(II) and 1.0mmol ligand BrBrBC, dissolve dichlorobis(dimethylsulfoxide)platinum(II) In 0.5 mL of dimethyl sulfoxide solution, dissolve the ligand BrBrBC in 3 mL of methanol and 1 mL of distilled water, then mix the two solutions into a polytetrafluoroethylene reactor, react at 100 °C for 48 hours, and cool After reaching room temperature, yellow blocky solids were precipitated, which were washed with methanol and diethyl ether in sequence, and complex 3 was obtained after vacuum drying with a yield of 92.26%.

[0064] The resulting yellow granular product is identified:

[0065] (1) Infrared spectrum, its spectrogram is as follows Figure 12 Shown:

[0066] IR(KBr):3206,1727,1614,1555,1448,1401,1247,1150,1110,1023,975,935,740,528,432cm -1 .

[0067] (2) Proton NMR spectrogram, its spectrogram is as Figure 9 shown.

[0068] 1 H NMR (600MHz, DMSO-d 6 )δ14.02(d, J=82.0Hz,...

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Abstract

The invention discloses a dihalogenated coumarin-platinum (II) complex and its synthesis method and application. The chemical structural formula of the complex is shown in Formula 1-Formula 3: the present invention uses anti-tumor activity Coumarin is the ligand skeleton, which is modified by organic synthesis to obtain dihalogenated coumarin derivatives, and then synthesized by coordination reaction with dichlorobis(dimethylsulfoxide)platinum(II) to obtain A complex with anti-tumor activity, further studies have found that the complex has a good inhibitory effect on cancer cells, and has less toxicity to normal cells. IC of the complex to cancer cells 50 The values ​​are all less than 10 μM; its antitumor activity in vitro is far greater than that of other classic cisplatin anticancer drugs, and it also shows superior antitumor activity in vitro than coumarin ligands, and its IC on normal cells 50 The values ​​are all greater than 100 μM, so the complexes of the present invention can be used in the preparation of various antitumor drugs.

Description

technical field [0001] The invention relates to a platinum (II) complex and its synthesis method and application, in particular to a dihalogenated coumarin-platinum (II) complex and its synthesis method and application. Background technique [0002] Malignant tumors are one of the most closely related diseases to human beings. Its morbidity and mortality are extremely high, which poses a serious threat to human health. According to the survey and statistics of the World Health Organization, there are millions of cancer patients who die of malignant tumors every year worldwide, and this number is still rising. At present, there are generally two problems with antitumor drugs, one is the drug resistance of tumor cells to the drugs, and the other is toxic and side effects. Platinum anticancer drugs are the most important chemotherapeutic drugs for clinical treatment of tumors, accounting for more than 50% of the relevant chemotherapeutic drugs used in clinical practice. Altho...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00A61P35/00
CPCC07F15/0093
Inventor 王书龙覃其品谭明雄韦庆敏荣建贤罗志辉陈渊
Owner YULIN NORMAL UNIVERSITY
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