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Platinum (II) complex by taking chiral compound as ligand as well as synthetic method and application of platinum (II) complex

A synthesis method and technology of complexes, which are applied in the field of medicine to achieve the effects of good medicinal value and significant in vitro anti-tumor activity

Inactive Publication Date: 2015-03-04
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Many endogenous substances, including enzymes, receptors, carriers, etc., have chirality. The chiral environment of the human body and specific enantiomeric interactions lead to chiral drug enantiomers in pharmacokinetics and pharmacodynamics. The difference in stereoselectivity in science complicates the clinical application of chiral drugs
There are no related reports on the synthesis and pharmacological activity of metal complexes using the chiral 4-(2,3-dihydroxypropyl)-formamide-6-azabenzanthrone as an active ligand.

Method used

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  • Platinum (II) complex by taking chiral compound as ligand as well as synthetic method and application of platinum (II) complex
  • Platinum (II) complex by taking chiral compound as ligand as well as synthetic method and application of platinum (II) complex
  • Platinum (II) complex by taking chiral compound as ligand as well as synthetic method and application of platinum (II) complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Accurately weigh 0.5mmol of R-(+)-L and 0.5mmol of dichlorobis(dimethylsulfoxide) platinum(II), dissolve R-(+)-L in 40mL of 100v In / v% methanol, dichlorobis(dimethylsulfoxide) platinum (II) was dissolved in 10mL of water, the two solutions were mixed, reacted at 80°C for 28 hours, concentrated and evaporated to remove most of the solvent (solvent 85% of the added amount), cooled to room temperature and stood still, and a dark green solid product was precipitated (yield 95%).

[0048] The obtained dark green solid product is identified:

[0049] (1), infrared spectrum, its spectrogram is as follows figure 1 shown.

[0050] IR(KBr):3406,3066,3000,2912,2346,1599,1564,1509,1457,1407,1317,1286,1202,1118,1026,944,764,691,606,521cm -1 .

[0051] (2), proton nuclear magnetic resonance spectrogram, its spectrogram is as figure 2 shown.

[0052] 1 H NMR (500MHz, DMSO-d 6 )δ9.06(s,1H),8.93–8.91(m,1H),8.81(d,J=7.4Hz,1H),8.61(d,J=8.1Hz,1H),8.38(d,J=8.5 Hz,1H),8.33(dd,J=7....

Embodiment 2

[0064] Accurately weigh 0.5mmol of S-(–)-L and 0.5mmol of dichlorobis(dimethylsulfoxide) platinum(II), dissolve S-(–)-L in 30mL of 80v Dissolve dichlorobis(dimethylsulfoxide) platinum (II) in 25mL of 90v / v% ethanol in / v% methanol, mix the two solutions, react at 75°C for 24 hours, concentrate and evaporate to remove After most of the solvent (80% of the added amount of solvent), it was cooled to room temperature and stood still, and a dark green solid product was precipitated (yield 90%).

[0065] The obtained dark green solid product is identified:

[0066] (1), infrared spectrum, its spectrogram is as follows Figure 5 shown.

[0067] IR(KBr):3481,3736,3066,2863,2363,1997,1638,1602,1542,1473,1457,1410,1388,1353,1317,1281,1262,1218,1199,1163,1106,1095,1040 ,966,938,916,875,831,798,765,694,604,573,494cm -1 .

[0068] (2), proton nuclear magnetic resonance spectrogram, its spectrogram is as Figure 6 shown.

[0069] 1 H NMR (500MHz, DMSO-d 6 )δ9.06(s,1H),8.92–8.90(m,1...

Embodiment 3

[0082] Accurately weigh 0.5mmol of R-(+)-L and 1.5mmol of dichlorobis(dimethylsulfoxide) platinum(II), dissolve R-(+)-L in 60mL of In a mixed solution of 100v / v% methanol and 100v / v% ethanol (the volume ratio of 100v / v% methanol and 100v / v% ethanol is 6:7), dichlorobis(dimethylsulfoxide) Platinum (II) was dissolved in 30mL of a mixed solution consisting of water and 100v / v% methanol (the volume ratio of water and 100v / v% methanol was 1:99), and the two solutions were mixed and reacted at 90°C for 36 hours , concentrated and evaporated to remove most of the solvent (88% of the added amount of solvent), cooled to room temperature and left to stand, and a dark green solid product (yield 85%) was precipitated.

[0083] The obtained dark green solid product was detected by infrared spectroscopy, NMR, and electrospray mass spectrometry, and it could be determined that the obtained product was R-(+)-Pt.

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Abstract

The invention discloses a platinum (II) complex by taking chiral 4-(2,3-dyhydroxylpropyl)-methanamide-6-aza-benzanthrone as a ligand as well as a synthetic method and application of the platinum (II) complex. The synthetic method of the complex comprises the following steps: dissolving (+)-4-(2,3-dyhydroxylpropyl)-methanamide-6-aza-benzanthrone or (-)-4-(2,3-dyhydroxylpropyl)-methanamide-6-aza-benzanthrone and dichloro.bi(dimethyl sulfoxide)mixed platinum (II) in a polar solvent, mixing to carry out a complexing reaction, thereby obtaining the platinum (II) complex. The complex obtained by the inventor has obvious in-vitro antitumor activity, the in-vitro antitumor activity of a tested tumor strain is universally higher than that of an original chiral ligand, and the complex has high potential medicinal value and is expected to be used for preparing various antitumor medicines. The structural formulas of the complex disclosed by the invention are respectively shown in the formulas (I) and (II) in the specification.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a platinum (II) complex with chiral 4-(2,3-dihydroxypropyl)-formamide-6-azabenzanthrone as a ligand and a synthesis method thereof and apply. Background technique [0002] Malignant tumor is one of the most important diseases that threaten human life, and its mortality rate accounts for the second of all diseases, about 25%, second only to cardiovascular diseases. Chemotherapy is one of the four traditional treatment methods for malignant tumors. It is widely used clinically and occupies an important position. At present, due to various complex factors such as industrial scale expansion and environmental pollution, the incidence of cancer in my country is in a stage of rapid increase. Research and development of new anticancer drugs is a major strategy and hot direction in the field of medicine and health. [0003] In 1965, Rosenberg B. of the United States discovered that ci...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61K31/555A61P35/00
CPCC07F15/0013
Inventor 陈振锋梁宏刘延成覃其品黎玉兰徐青民申文英
Owner GUANGXI NORMAL UNIV
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