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Iridium complex constructed based on 8-hydroxyquinoline derivative and 1-phenylpyrazole iridium dimer as well as synthesis method and application of iridium complex

A synthesis method and technology of complexes, applied in the field of medicine, can solve the problems of limited therapeutic effect and long-term use, neurotoxicity and bone marrow suppression, toxic and side effects, etc.

Active Publication Date: 2020-05-08
煌途医药(无锡)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the large amount of clinical use of platinum drugs such as cisplatin 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.)
At present, there are no relevant reports on iridium complexes constructed with almost inactive 8-hydroxyquinoline derivatives and 1-phenylpyrazole iridium dimers and their synthesis methods and applications

Method used

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  • Iridium complex constructed based on 8-hydroxyquinoline derivative and 1-phenylpyrazole iridium dimer as well as synthesis method and application of iridium complex
  • Iridium complex constructed based on 8-hydroxyquinoline derivative and 1-phenylpyrazole iridium dimer as well as synthesis method and application of iridium complex
  • Iridium complex constructed based on 8-hydroxyquinoline derivative and 1-phenylpyrazole iridium dimer as well as synthesis method and application of iridium complex

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1: the synthesis of complex Ir1

[0037]In a 100.0mL round bottom flask, add 2.0mmol of chloroquinaldol (H-QL1) and 1.0mmol of 1-phenylpyrazole iridium dimer, and then add 5.5mL of organic solvent (by 5.0mL of ethanol and 0.5 mL of dimethyl sulfoxide), stirred and dissolved, and reacted at 65°C until complete (about 15h), stopped the reaction, cooled to room temperature, reddish-brown crystals were precipitated, collected and dried to obtain a reddish-brown solid product. Yield 85.50%.

[0038] The product obtained in this embodiment is characterized:

[0039] (1) X-ray single crystal diffraction

[0040] 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...

Embodiment 2

[0057] Embodiment 2: the synthesis of complex Ir1

[0058] Example 1 was repeated, except that the organic solvent was changed to ethanol, and the amount used remained unchanged; the reaction was changed to 30° C. (about 38 hours to complete the reaction).

[0059] The result is reddish-brown crystals. Yield 62.34%.

[0060] Single crystal diffraction analysis, elemental analysis, infrared analysis and mass spectrometry analysis were performed on the product obtained in this example, and it was determined that the obtained reddish-brown crystal was the target complex Ir1.

Embodiment 3

[0061] Embodiment 3: the synthesis of complex Ir2

[0062] In a 100.0 mL round bottom flask, add 2.0 mmol of 5,7-dibromo-2-methyl-8-hydroxyquinoline (H-QL2) and 1.0 mmol of 1-phenylpyrazole iridium dimer, Then add 14.0mL of organic solvent (composed of 3.5mL of ethanol and 10.5mL of chloroform), stir to dissolve, carry out the reaction at 65°C until complete (about 29h), stop the reaction, cool to room temperature, and reddish-brown crystals precipitate out , the crystals were collected and dried to obtain a reddish-brown solid product. Yield 70.21%.

[0063] The product obtained in this embodiment is characterized:

[0064] (1) X-ray single crystal diffraction

[0065] 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 the above Table 1, and some bond length and bond angle data are shown in the following Table 5 and ...

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Abstract

The invention discloses an iridium complex constructed based on a 8-hydroxyquinoline derivative and a 1-phenylpyrazole iridium dimer as well as a synthesis method and application of the iridium complex. The synthesis method of the iridium complex comprises the following steps: putting the 1-phenylpyrazole iridium dimer and the 8-hydroxyquinoline derivative into an organic solvent, and reacting under a heating or non-heating condition to obtain the corresponding target complex. A test result shows that the complex has remarkable biological activity (the activity is remarkably higher than that of ligand and cisplatin the complex) on cervical cancer and ovarian cancer cells, and meanwhile, the toxicity of the complex on human normal hepatocytes is extremely low (IC50 is greater than 80 [mu] M); on the other hand, the complex disclosed by the invention can also be used for fluorescence localization in tumor cells, and can be developed into a targeting anti-cancer drug for fluorescence localization targeting mitochondria.

Description

technical field [0001] The invention relates to an iridium complex constructed on the basis of 8-hydroxyquinoline derivatives and 1-phenylpyrazole iridium dimer 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 th...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61K31/555A61P35/00A61K49/00C09K11/06C09B57/00
CPCA61K49/0021A61P35/00C07B2200/13C07F15/0033C09B57/00C09K11/06C09K2211/185
Inventor 邹华红蒙婷梁福沛
Owner 煌途医药(无锡)有限公司
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