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High-activity coumarin-platinum (II) complex targeting ovarian cancer and synthesis method and application thereof

An ovarian cancer, highly active technology, applied in the direction of organic active ingredients, platinum-group organic compounds, platinum-based organic compounds, etc., to achieve the effect of good aromatic planarity

Active Publication Date: 2018-10-16
YULIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] There are few reports on the synthesis and application of platinum (II) complexes targeting ovarian cancer with coumarin and its derivatives as ligands.

Method used

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  • High-activity coumarin-platinum (II) complex targeting ovarian cancer and synthesis method and application thereof
  • High-activity coumarin-platinum (II) complex targeting ovarian cancer and synthesis method and application thereof
  • High-activity coumarin-platinum (II) complex targeting ovarian cancer and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Accurately weigh the amount of the substance as 1.0mmol dichlorobis(dimethylsulfoxide) platinum (II) and 1.0mmol MeOBC ligand, and dissolve the dichlorobis(dimethylsulfoxide) platinum (II) In 1mL of dimethyl sulfoxide solution, dissolve the MeOBC ligand in 3mL of methanol, then mix the two solutions, react at 90°C for 48 hours, let it stand and cool to room temperature, a yellow blocky solid is precipitated, and the solid is sequentially used After washing with distilled water, methanol and ether, and drying in vacuum, complex 1 was obtained with a yield of 91.3%.

[0046] Identify the resulting yellow blocky crystals:

[0047] (1) Infrared spectrum, its spectrogram is as follows Figure 4 shown.

[0048] IR(KBr):3311,3024,2924,1713,1604,1577,1467,1436,1272,1121,1104,1032,953,778,754,537,438cm -1 .

[0049] (2) Proton NMR spectrogram, its spectrogram is as figure 1 shown.

[0050] 1H NMR (600MHz, DMSO-d6) δ13.95 (d, J = 83.9Hz, 1H), 9.90 (d, J = 247.6Hz, 1H), 8.2...

Embodiment 2

[0058] Accurately weigh the amount of the substance as 1.0mmol dichlorobis(dimethylsulfoxide) platinum (II) and 1.0mmol OHBC ligand, dissolve dichlorobis(dimethylsulfoxide) platinum (II) In 1 mL of dimethyl sulfoxide solution, dissolve the OHBC ligand in 4 mL of methanol, then mix the two solutions, react at 90 ° C for 24 hours, let it stand and cool to room temperature, and precipitate a yellow needle-like solid, which is sequentially used After washing with distilled water, methanol and ether, the compound 2 was obtained after vacuum drying with a yield of 85.3%.

[0059] The resulting yellow needle-like solid product is identified:

[0060] (1) Infrared spectrum, its spectrogram is as follows Figure 8 shown.

[0061] IR (KBr): 3325, 3005, 1702, 1606, 1577, 1515, 1435, 1290, 1142, 1092, 1018, 976, 750, 730, 543, 510, 438cm-1.

[0062] (2) Proton NMR spectrogram, its spectrogram is as Figure 5 shown.

[0063] 1H NMR (600MHz, DMSO-d6) δ13.92(d, J=84.1Hz, 1H), 10.62(s, 1...

Embodiment 3

[0071] Accurately weigh 1.0 mmol of dichloro-bis(dimethylsulfoxide) platinum (II) and 1.0 mmol of BC ligand, dissolve dichloro-bis(dimethyl sulfoxide) platinum (II) Dissolve the BC ligand in 3 mL of methanol in 0.5 mL of dimethyl sulfoxide solution, then mix the two solutions, react at 90 ° C for 48 hours, cool to room temperature, and precipitate a yellow granular solid. After washing and vacuum drying, complex 3 was obtained with a yield of 76.22%.

[0072] The obtained yellow granular solid is identified:

[0073] (1) Infrared spectrum, its spectrogram is as follows Figure 12 shown.

[0074] IR (KBr): 3328, 3302, 3005, 1712, 1605, 1572, 1434, 1319, 1140, 1106, 1024, 741, 440cm-1.

[0075] (2) Proton NMR spectrogram, its spectrogram is as Figure 9 shown.

[0076] 1H NMR (600MHz, DMSO-d6) δ13.95(d, J=88.0Hz, 1H), 9.89(d, J=251.9Hz, 1H), 8.23(t, J=7.9Hz, 1H), 7.99(ddd ,J=7.4,5.6,1.3Hz,1H),7.87-7.83(m,1H),7.55(ddd,J=8.2,4.7,0.7Hz,1H),7.49(ddd,J=9.0,5.4,2.8Hz ,2H), 7.42...

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Abstract

The invention discloses a high-activity coumarin-platinum (II) complex targeting the ovarian cancer and a synthesis method and application thereof. The complex adopts a chemical structural formula shown as one of formulae 1-5. A coumarin derivative is modified by natural coumarin as a skeleton, and then reacts with metal platinum (II) to form a complex so as to obtain the coumarin platinum (II) complex with higher activity. The in-vitro antitumor activity of the complex is far higher than that of other classical cisplatin anticancer medicines, and the complex also shows in-vitro antitumor activity superior to that of a coumarin ligand; the complex has a potential medicinal value and is expected to be applied to preparation of various antitumor medicines.

Description

technical field [0001] The invention relates to a platinum (II) complex and its synthesis method and application field, in particular to a highly active coumarin-platinum (II) complex targeting ovarian cancer, its synthesis method and application. Background technique [0002] With the development of economy and the change of lifestyle, the prevalence of cancer is getting higher and higher, seriously threatening human life and health. According to the statistics of the World Health Organization, cancer is a common and frequently-occurring disease that seriously threatens human health and life. It has become the second cause of human death and one of the most difficult diseases to treat. At present, platinum-based 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. Although cisplatin was approved by the FDA in 1978 as the first generatio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61P35/00A61K31/555
CPCA61P35/00C07F15/0093
Inventor 王书龙覃其品谭明雄李佳雅罗冬妹王振凤
Owner YULIN NORMAL UNIVERSITY
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