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Iridium complex constructed based on 8-hydroxyquinoline derivative and 2-phenylpyridine iridium dimer and synthesis method and application thereof

A synthesis method and complex technology, applied in the field of medicine, can solve problems such as the synthesis method and application of iridium complexes, obvious side effects, etc.

Active Publication Date: 2020-04-28
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

Despite their significant impact as anticancer drugs, the significant side effects of these drugs coupled with their inherent lack of resistance have prompted researchers to develop new non-platinum metal anticancer drugs
However, there are no relevant reports on iridium complexes constructed with 8-hydroxyquinoline derivatives and 2-phenylpyridine iridium dimers and their synthesis methods and applications.

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  • Iridium complex constructed based on 8-hydroxyquinoline derivative and 2-phenylpyridine iridium dimer and synthesis method and application thereof
  • Iridium complex constructed based on 8-hydroxyquinoline derivative and 2-phenylpyridine iridium dimer and synthesis method and application thereof
  • Iridium complex constructed based on 8-hydroxyquinoline derivative and 2-phenylpyridine iridium dimer and synthesis method and application thereof

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Experimental program
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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 2-phenylpyridine iridium dimer, and then add 16.5mL of organic solvent (by 15.0mL of ethanol and 1.5mL Composition of water), stirred to dissolve, reacted at 70°C until complete (about 12h), stopped the reaction, cooled to room temperature, reddish-brown crystals were precipitated, collected and dried to obtain a reddish-brown solid product. Yield 90.21%.

[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 is as ...

Embodiment 2

[0059] Embodiment 2: the synthesis of complex Ir1

[0060] Example 1 was repeated, except that the organic solvent was changed to ethanol, and the amount used remained unchanged; the reaction was changed to 100° C. (the reaction was completed for about 6 hours).

[0061] The result is reddish-brown crystals. Yield 85.31%.

[0062] 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

[0063] Embodiment 3: the synthesis of complex Ir2

[0064] In a 100.0mL round bottom flask, add 2.0mmol of 5,7-dibromo-2-methyl-8-hydroxyquinoline (H-QL2) and 1.0mmol of 2-phenylpyridine iridium dimer respectively, and then Add 16.5mL of organic solvent (consisting of 3.5mL of ethanol and 10.5mL of chloroform), stir to dissolve, carry out the reaction at 65°C until complete (about 27h), 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 80.46%.

[0065] The product obtained in this embodiment is characterized:

[0066] (1) X-ray single crystal diffraction

[0067] 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 followi...

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Abstract

The invention discloses an iridium complex constructed based on 8-hydroxyquinoline derivative and 2-phenylpyridine iridium dimer and a synthesis method and application thereof. The synthesis method ofthe iridium complex comprises the following steps: putting a 2-phenylpyridine iridium dimer and an 8-hydroxyquinoline derivative into an organic solvent, and performing reacting under a heating or non-heating condition to obtain the corresponding target complex. A test result of an applicant shows that the complex has remarkable biological activity (the activity is remarkably higher than that ofligands and cisplatin of cervical cancer and ovarian cancer cells) 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); and moreover, the complex disclosed by the invention can also be used for fluorescence localization in tumor cells, and can be developed into a targeting anti-cancerdrug 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 2-phenylpyridine iridium dimers, a synthesis method and application thereof, belonging to the technical field of medicine. Background technique [0002] At present, tumor seems to be the second leading disease of human death, which seriously endangers the physical and mental health of the people. Common malignant tumors include lung cancer, cervical cancer, breast cancer, liver cancer, lymphoma, leukemia and other types. Clinically, platinum-based antineoplastic drugs are still one of the most important chemotherapeutic drugs for tumor treatment, accounting for more than 50% of clinical chemotherapeutic drug applications. The main target of this type of drug against cancer is double-stranded DNA, and the main mechanism of action is to interfere with the double-strand replication of DNA in tumor cells, thereby exerting the goal of restraining cell...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09B57/10C09K11/06A61P35/00A61K31/555A61K49/00
CPCA61P35/00C07F15/0033
Inventor 蒙婷邹华红梁福沛
Owner 煌途医药(无锡)有限公司
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