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Synthesis method and application of platinum (II) complex using 2-benzoylpyridine as ligand

A technology of benzoylpyridine and its synthesis method, which is applied in the field of medicine, can solve the problems of clinical application limitation, low water solubility, DNA structure damage, etc., and achieve the effect of good selectivity, low toxicity, and significant in vitro anti-tumor activity

Inactive Publication Date: 2015-05-13
AFFILIATED HOSPITAL OF GUILIN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, due to side effects such as low water solubility, severe toxicity, drug resistance and gastrointestinal reactions of cisplatin, its clinical application has been significantly limited; thus, a series of less toxic or drug-resistant platinum Antineoplastic drugs are produced on this basis, such as carboplatin, oxaliplatin, leproplatin, heptaplatin and other second- and third-generation platinum-based drugs, and have the opportunity to enter the clinical research stage
Metal complexes have their own unique advantages, such as the effect of platinum-containing drugs on DNA structure damage, so far no organic drug can surpass

Method used

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  • Synthesis method and application of platinum (II) complex using 2-benzoylpyridine as ligand
  • Synthesis method and application of platinum (II) complex using 2-benzoylpyridine as ligand
  • Synthesis method and application of platinum (II) complex using 2-benzoylpyridine as ligand

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Accurately weigh 0.5 mmol of 2-benzoylpyridine and 0.5 mmol of dichlorobis(dimethylsulfoxide) platinum (II), and dissolve 2-benzoylpyridine in 37 mL of 100% ( volume) in methanol, dichlorobis(dimethylsulfoxide) platinum (II) was dissolved in 9.5mL of water, the two solutions were mixed, reacted at 78°C for 24h, concentrated and evaporated to remove most of the solvent (solvent added 89% of the amount), cooled to room temperature, and stood still, and a yellow solid product was precipitated (yield 96%).

[0036] The resulting yellow solid product is identified:

[0037] (1), infrared spectrum, its spectrogram is as follows figure 1 shown.

[0038] IR(KBr):3441,1663,1598,1574,1444,1283,932,754,703,647cm -1 .

[0039] (2), proton nuclear magnetic resonance spectrogram, its spectrogram is as figure 2 shown.

[0040] 1 H NMR (600MHz, DMSO-d 6 )δ8.73–8.69(m,1H),8.06(td,J=7.7,1.7Hz,1H),8.00–7.93(m,3H),7.68–7.64(m,2H),7.53(t,J= 7.8Hz, 2H).

[0041] (3), carbon nuclear ...

Embodiment 2

[0052] Accurately weigh 0.5 mmol of 2-benzoylpyridine and 0.5 mmol of dichlorobis(dimethylsulfoxide) platinum (II), and dissolve 2-benzoylpyridine in 56 mL of 65% ( (volume) methanol and 75% (volume) ethanol (the volume ratio of 65% (volume) methanol and 75% (volume) ethanol is 5:8), dichloro two (dimethyl sulfoxide) Dissolve platinum (II) in a mixed solution of 25mL of water and 98% (volume) methanol (the volume ratio of water and 98% (volume) methanol is 1:98), mix the two solutions, react at 60°C for 32h, and concentrate After most of the solvent was removed by evaporation (85% of the solvent addition), it was cooled to room temperature and left to stand, and a yellow-green solid product (yield 84%) was separated out, and the obtained yellow solid product was determined to be the compound shown in the above formula (I) through structural characterization. compound.

Embodiment 3

[0054] Accurately weigh 0.5mmol of 2-benzoylpyridine and 0.5mmol of dichlorobis(dimethylsulfoxide)platinum(II), add the two to a 20cm Pyrex thick-walled glass tube with one end closed Add dropwise 80% (volume) methanol 3.5mL, dropwise add dimethyl sulfoxide 0.8mL, freeze the mixture with liquid nitrogen, seal its open end under vacuum conditions, mix well and place at 50°C Reacted in an oven for 72 hours to obtain a yellow solid product (yield 78%), which was determined to be the compound represented by the above formula (I) through structural characterization.

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Abstract

The invention discloses a synthesis method and application of a platinum (II) complex using 2-benzoylpyridine as a ligand. The platinum (II) complex using 2-benzoylpyridine as a ligand is disclosed as Formula (I). The synthesis method comprises the following steps: weighing 2-benzoylpyridine and platinum dichlorodi(dimethyl sulfoxide) (II) according to the mole ratio of 1:1, dissolving in a polar solvent, and carrying out complexing reaction to obtain the target product, wherein the polar solvent is composed of water and one or composition of more than two of methanol, ethanol, acetone and dimethyl sulfoxide. The inspection of the applicator on the proliferation inhibiting activity of the complex on multiple liver cancer cell strains proves that the complex has obvious in-vitro antitumor activity, has very low toxicity for normal hepatic cells HL-7702, has favorable potential pharmaceutical value, and is hopeful to be used for preparing anti-liver-cancer drugs.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a synthesis method and application of a platinum (II) complex with 2-benzoylpyridine as a ligand. Background technique [0002] Cancer is one of the major chronic diseases that seriously endanger human health. The development trend of cancer disclosed by the World Health Organization shows that the number of deaths in 2015 is expected to reach 9 million (Si Yuchang, et al. Journal of Armed Police Medical College, 2006, 15(1): 64-65), and the fatality rate is about It accounts for 25% of the diseases in the world today, and accounts for the second place in the death rate of all diseases, second only to cardiovascular diseases. Due to the continuous expansion of industrial scale in the world today, the influence of environmental pollution and other factors, the incidence of cancer in various countries in the world is increasing rapidly. Therefore, research and development of one ...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61P35/00
CPCC07F15/0093
Inventor 金俊飞黎玉兰何松青
Owner AFFILIATED HOSPITAL OF GUILIN MEDICAL UNIV
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