Ruthenium (II) complex using chiral compound as ligand as well as synthesis method and application of Ruthenium (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: 2015-03-25
GUANGXI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Ruthenium (II) complex using chiral compound as ligand as well as synthesis method and application of Ruthenium (II) complex
  • Ruthenium (II) complex using chiral compound as ligand as well as synthesis method and application of Ruthenium (II) complex
  • Ruthenium (II) complex using chiral compound as ligand as well as synthesis method and application of Ruthenium (II) complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Accurately weigh 0.5mmol of R-(+)-L and 0.5mmol of dichlorotetrakis(dimethylsulfoxide)ruthenium(II), and dissolve R-(+)-L in 55mL of 100v In / v% ethanol, dichloro tetrakis (dimethyl sulfoxide) ruthenium (II) is dissolved in the water of 15mL, two kinds of solutions are mixed, react at 80 ℃ for 24 hours, concentrate and evaporate to remove most of solvent (solvent 82% of the added amount), after cooling to room temperature, the dark green solid product was precipitated (yield 85%).

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

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

[0050] IR(KBr):3442,3060,2918,2374,1651,1602,1568,1553,1473,1449,1416,1388,1353,1317,1281,1224,1202,1166,1147,1086,1020,9568,938,8076,20,5cm -1 .

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

[0052] 1 H NMR (500MHz, DMSO-d 6 )δ10.58(s,1H),9.27(t,J=5.7Hz,1H),8.95(d,J=7.6Hz,1H),8.69–8.61(m,2H),8...

Embodiment 2

[0064] Accurately weigh 0.5mmol of S-(–)-L and 0.5mmol of dichlorotetrakis(dimethylsulfoxide) ruthenium(II), dissolve S-(–)-L in 40mL of 80v Dissolve dichlorotetrakis(dimethylsulfoxide)ruthenium(II) in 35mL of 88v / v% ethanol in / v% methanol, mix the two solutions, react at 85°C for 24 hours, concentrate and evaporate to remove After most of the solvent (80% of the added amount of the solvent) was cooled to room temperature, the dark green solid product was precipitated (yield 80%).

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

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

[0067] IR(KBr):3369,3066,2962,2923,2368,1651,1602,1566,1556,1473,1440,1416,1388,1353,1320,1281,1259,1224,1202,1166,1141,1094,1048 ,1018,968,938,834,801,771,680,661,609,532,499cm-1 .

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

[0069] 1 H NMR (500MHz, DMSO-d 6 )δ10.57(s,1H),9.24–9.22(m,1H),9.09(d,J...

Embodiment 3

[0081] Accurately weigh 0.5mmol of R-(+)-L and 1.5mmol of dichlorotetrakis(dimethylsulfoxide) ruthenium(II), and dissolve R-(+)-L in 65mL 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 71:63), dichlorotetrakis(dimethylsulfoxide) Ruthenium (II) was dissolved in 9 mL of a mixed solution consisting of water and 100v / v% methanol (water and 100v / v% methanol volume ratio 13:87), and the two solutions were mixed and reacted at 90°C for 36 hours, After concentrating and evaporating to remove most of the solvent (78% of the added amount of solvent), it was cooled to room temperature and left standing, and a dark green solid product was precipitated (yield 75%).

[0082] 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-(+)-Ru.

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Abstract

The invention discloses a ruthenium (II) complex using chiral 4-(2,3-dihydroxypropyl)-formamide-6-azabenzanthrone as a ligand as well as a synthesis method and an application of the Ruthenium (II) complex. The synthesis method of the complex comprises the following steps: dissolving (+)-4-(2,3-dihydroxypropyl)-formamide-6-azabenzanthrone or (-)-4-(2,3-dihydroxypropyl)-formamide-6-azabenzanthrone and dichloro-tetra(dimethyl sulfoxide) ruthenium (II) into a polar solvent, then mixing, and performing complexing reaction to obtain the complex. The applicant discovers that the obtained complex has significant in-vitro anti-tumor activity, the in-vitro anti-tumor activity of tested tumor strains is universally higher than that of the original chiral ligand, and the complex has good potential medicinal value and is expected to be applied to preparation of various anti-tumor medicaments. The structural formula of the complex is respectively shown in formula (I) and formula (II) in the specification.

Description

technical field [0001] The invention relates to the field of medical technology, in particular to a ruthenium (II) complex with chiral 4-(2,3-dihydroxypropyl)-formamide-6-azabenzanthrone as a ligand and a synthesis method thereof and apply. Background technique [0002] Cancer mainly refers to malignant tumors. It is a frequently-occurring and common disease that seriously endangers human health. It seriously endangers human life and health. Due to the influence of various external factors such as environmental pollution, the incidence of cancer is currently in a stage of rapid increase. According to statistics, the death rate caused by cancer in the world has been second only to cardiovascular and cerebrovascular diseases. Therefore, the research and development of new anticancer drugs is one of the major strategies and hot spots in the medical field. Chemotherapy (i.e. chemotherapy) is one of the main means of treating malignant tumors. It is widely used clinically and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61K31/555A61P35/00
CPCC07F15/0053
Inventor 梁宏陈振锋刘延成覃其品黎玉兰徐青民江燕华
Owner GUANGXI NORMAL UNIV
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