Low-toxicity iridium complexes and synthesis method and application thereof

A synthesis method and complex technology, applied in the field of medicine, can solve problems affecting patients' health and normal medical treatment, and achieve significant biological activity

Active Publication Date: 2020-04-21
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although cisplatin and its cisplatin-like drugs have good effects in the treatment of cancer, cisplatin-based drugs also have toxicities such as nephrotoxicity and drug resistance that cannot be ignored on human health, affecting the health and safety o

Method used

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  • Low-toxicity iridium complexes and synthesis method and application thereof
  • Low-toxicity iridium complexes and synthesis method and application thereof
  • Low-toxicity iridium complexes and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: the synthesis of complex Ir1

[0031] In a 100.0mL round bottom flask, add 2.0mmol of chloroquinaldol (H-QL1) and 1.0mmol of 3-methyl-2-phenylpyridine iridium dimer, then add 28.7mL of organic solvent (by 28.0mL ethanol and 0.7mL of acetone), stirred and dissolved, and reacted at 85°C until complete (about 5h), stopped the reaction, cooled to room temperature, and reddish-brown crystals were precipitated, collected and dried to obtain a reddish-brown solid product. Yield 95.3%.

[0032] The product obtained in this embodiment is characterized:

[0033] (1) X-ray single crystal diffraction

[0034] 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 a...

Embodiment 2

[0054] Embodiment 2: the synthesis of complex Ir1

[0055] Example 1 was repeated, except that the organic solvent was changed to consist of 1.0 mL of ethanol, 5.0 mL of DMF and 14.0 mL of dichloromethane; the reaction was changed to 35° C. (about 18 h to complete the reaction).

[0056] The result is reddish-brown crystals. Yield 90.12%.

[0057] 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

[0058] Embodiment 3: the synthesis of complex Ir2

[0059] In a 100.0mL round bottom flask, add 2.0mmol of 5,7-dibromo-8-hydroxyquinoline (H-QL5) and 1.0mmol of 3-methyl-2-phenylpyridine iridium dimer, and then Add 20.0mL of organic solvent (consisting of 10.0mL of ethanol and 10.0mL of water), stir to dissolve, carry out the reaction at 100°C until complete (about 47h), stop the reaction, cool to room temperature, reddish-brown crystals precipitate, collect the crystals , dried to obtain a reddish-brown solid product. Yield 79.6%.

[0060] The product obtained in this embodiment is characterized:

[0061] (1) X-ray single crystal diffraction

[0062] 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 Table 6 respectivel...

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Abstract

The invention discloses three low-toxicity iridium complexes, and a synthesis method and an application thereof. The synthesis method of the iridium complexes comprises the following steps: taking andputting a 3-methyl-2-phenylpyridine iridium dimer and an 8-hydroxyquinoline derivative into an organic solvent, and reacting under a heating or non-heating condition to obtain the corresponding target complexes. Test results of the applicant show that the complexes have remarkable biological activity (the activity is remarkably higher than that of ligands and cis-platinum of the complexes) on cervical cancer and ovarian cancer cells, have extremely low toxicity (IC50 is more than 80 [mu]M) on human normal hepatocytes, and are expected to be developed into anti-tumor drugs.

Description

technical field [0001] The invention relates to a low-toxic iridium complex and its synthesis method and application, belonging to the technical field of medicine. Background technique [0002] Malignant tumors are still one of the major diseases that endanger human health today. With cisplatin cis-[PtCl 2 (NH 3 ) 2 ] can inhibit the proliferation of many cancer cells such as bladder cancer, breast cancer, ovarian cancer, lymphoma, testicular cancer and leukemia, which opened up a new field of research on metal-based anti-tumor inorganic drugs. Although cisplatin and its cisplatin-like drugs have good effects in the treatment of cancer, cisplatin-based drugs also have toxicities such as nephrotoxicity and drug resistance that cannot be ignored on human health, affecting the health and safety of patients. normal medical treatment. Therefore, it is necessary to obtain new anticancer drugs with lower toxicity. [0003] Hydroxyquinolines are considered to be a special stru...

Claims

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Application Information

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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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