Iridium complex as well as synthesis method and application thereof

A synthetic method and compound technology, applied in the field of medicine, can solve the problem of low liver cell toxicity and achieve significant biological activity

Active Publication Date: 2020-04-03
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, 8-hydroxyquinoline is used as a pharmaceutical intermediate, but it has not been seen that 5-chloro-8-hydroxyquinoline and 7,8-benzoquinoline iridium dimer are used as ligands to make the obtained iridium complex Reports that the drug has significant biological activity on tumor cells and has low toxicity to normal human liver cells

Method used

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  • Iridium complex as well as synthesis method and application thereof
  • Iridium complex as well as synthesis method and application thereof
  • Iridium complex as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] In a 100.0mL round bottom flask, add 2.0mmol of 5-chloro-8-hydroxyquinoline and 1.0mmol of 7,8-benzoquinoline iridium dimer, and then add 15.5mL of organic solvent (from 15.0mL of ethanol and 0.5mL of dimethyl sulfoxide), stirred to dissolve, reacted at 55°C until complete (about 8h), stopped the reaction, cooled to room temperature, reddish-brown crystals were precipitated, collected and dried to obtain reddish-brown solid product. Yield 79.99%.

[0021] The product obtained in this embodiment is characterized:

[0022] (1) X-ray single crystal diffraction

[0023] The reddish-brown crystal with perfect surface structure was measured by single crystal diffraction to determine its crystal structure. The obtained crystallographic and structural correction data are shown in Table 1 below, and the data of some bond lengths and angles are shown in Table 2 and Table 3 below. The crystal structure of reddish-brown crystals is as figure 1 shown.

[0024] Table 1. Crystall...

Embodiment 2

[0042] Example 1 was repeated, except that the organic solvent was changed to consist of 1.0 mL of ethanol and 15 mL of dichloromethane, and the reaction was carried out at 35° C. (about 50 h to complete the reaction).

[0043] The result is reddish-brown crystals. Yield 91.24%.

[0044] Single crystal diffraction analysis, elemental analysis, infrared analysis and mass spectrometry analysis were performed on the product obtained in this example, and the obtained reddish-brown crystal was determined to be the target compound.

Embodiment 3

[0046] Example 1 was repeated, except that the organic solvent was changed to consist of 3.0 mL of ethanol, 5.0 mL of water and 12.0 mL of acetone, and the reaction was carried out at 80° C. (about 35 h to complete the reaction).

[0047] As a result, reddish-brown crystals are obtained. Yield 80.55%.

[0048]Single crystal diffraction analysis, elemental analysis, infrared analysis and mass spectrometry analysis were performed on the product obtained in this example, and the obtained reddish-brown crystal was determined to be the target compound.

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Abstract

The invention discloses an iridium complex and a synthesis method and application thereof. The synthesis method of the iridium complex comprises the steps that 5-chloro-8-hydroxyquinoline and a 7, 8-benzoquinoline iridium dimer are added in an organic solvent, reaction is conducted under the heating or non-heating condition, and a target compound is obtained; wherein the organic solvent is ethanol, or a composition of ethanol and one or more than two selected from water, acetone, dichloromethane, trichloromethane, dimethyl sulfoxide and N, N-dimethylformamide. It is shown by test results in the invention that the iridium complex has remarkable biological activity (the activity is obviously higher than that of cis-platinum) on cervical cancer and ovarian cancer cells, and meanwhile, the toxicity of the iridium complex on normal hepatocytes of human body is extremely low (IC50 is higher than 80<mu>M).

Description

technical field [0001] The invention relates to an iridium complex and its synthesis method and application, belonging to the technical field of medicine. Background technique [0002] Cancer is one of the most serious malignant diseases threatening human life and health. At present, more than three million people die of cancer every year in our country, which has seriously threatened the life and health of our people. Platinum complexes such as cisplatin are currently one of the most widely used chemotherapeutic drugs and one of the first-choice drugs for the treatment of many cancers (Lippard, S.J.; et al. Chem. Sci., 2015, 6, 1189–1193.). However, the extensive use of platinum-based drugs such as cisplatin in clinical practice can easily lead to drug resistance and severe side effects such as nephrotoxicity, neurotoxicity and bone marrow suppression, which greatly limit their therapeutic effect and long-term use (Lippard, S.J.; et al. al. Chem. Sci., 2015, 6, 1189–1193....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61K31/555A61P35/00
CPCA61P35/00C07F15/0033
Inventor 邹华红蒙婷梁福沛
Owner GUANGXI NORMAL UNIV
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