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8-hydroxyquinoline derivative iridium (III) complex as well as preparation method and application thereof

A technology of hydroxyquinoline and derivatives, applied in the field of medicine, to achieve high anti-tumor activity and good target inhibition effect

Active Publication Date: 2021-04-20
YULIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But there is no iridium metal complex reported by 8-hydroxyquinoline derivatives

Method used

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  • 8-hydroxyquinoline derivative iridium (III) complex as well as preparation method and application thereof
  • 8-hydroxyquinoline derivative iridium (III) complex as well as preparation method and application thereof
  • 8-hydroxyquinoline derivative iridium (III) complex as well as preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0039] (1) 8-hydroxyquinoline derivative iridium (Ⅲ) complex [Ir (3a) (BQ) 2 ] preparation and characterization:

[0040] Such as Image 6 As shown, weigh compound 4 and compound 3a (8-hydroxyquinoline derivative) according to the molar ratio of 1:1.5, put them into the container, then add ethylene glycol, heat and reflux for 13h under the protection of argon, and obtain a dark red clear solution ; Cool to room temperature, add water to dilute, and then add saturated ammonium hexafluorophosphate solution, which produces a large amount of red precipitate; filter with suction, wash with water and ether, and dry; dissolve the dried crude product with acetonitrile, and filter with neutral alumina Column separation; use V (dichloromethane): V (acetonitrile) = 3: 1 mixed solvent to collect the yellow component, then distill under reduced pressure and spin dry to remove the solvent to obtain a khaki solid product, which is 8-hydroxyquinoline Phyloline derivatives iridium (Ⅲ) comple...

Embodiment 2

[0052] 8-Hydroxyquinoline derivatives iridium (Ⅲ) complexes [Ir (3a) (BQ) 2 ] The synthetic route such as Image 6 Shown:

[0053] (1) Preparation of compound 1: add 600mL of concentrated hydrochloric acid (pre-placed in the refrigerator to freeze, the concentration of concentrated hydrochloric acid is at 37% volume fraction) and 14.5g of 8-hydroxyquinoline in a 1L round bottom flask, and heat the temperature to 40°C , after the 8-hydroxyquinoline is completely dissolved, add 53g NaClO in batches 3 (The addition was completed within 60 minutes), and after the addition was completed, the stirring was continued at 40° C. for 2 h. After the reaction was completed, dilute to 2L with ice water and dilute with CH 2 Cl 2 (6 × 250mL) extraction, combined organic phase, washed with 3 × 200mL of distilled water, vacuum rotary evaporation of the solvent to obtain a yellow solid, filtered the precipitate, and the solid was recrystallized three times with 40mL of methanol to obtain 6,7...

Embodiment 3

[0059] 8-Hydroxyquinoline derivatives iridium (Ⅲ) complexes [Ir (3a) (BQ) 2 ] The synthetic route such as Image 6 Shown:

[0060] (1) Preparation of compound 1: carefully add 725mL of concentrated hydrochloric acid (placed in the refrigerator to freeze in advance, the concentration of concentrated hydrochloric acid is at 35% volume fraction) and 14.5g of 8-hydroxyquinoline in a 1L round bottom flask, and heat to 45 ℃, after the 8-hydroxyquinoline is completely dissolved, add 64g NaClO in batches 3 (The addition was completed within 60 minutes), and after the addition was completed, the stirring was continued at 45° C. for 1 h. After the reaction was completed, dilute to 2L with ice water and dilute with CH 2 Cl 2 (6 × 250mL) extraction, combined organic phase, washed with 3 × 200mL of distilled water, vacuum rotary evaporation of the solvent to obtain a yellow solid, filtered the precipitate, and the solid was recrystallized three times with 40mL of methanol to obtain 6,7...

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Abstract

The invention discloses an 8-hydroxyquinoline derivative iridium (III) complex as well as a preparation method and application thereof, and belongs to the field of medicines. The chemical name of the compound is 2-methylpyridino[3,2-a]-pyridino[1',2':1,2]imidazo[4,5-c]phenazine.bisbenzoquinolinyl iridium(III) hexafluorophosphate . The preparation method comprises the following steps: reacting 8-hydroxyquinoline with hydrochloric acid and NaClO3; adding anhydrous potassium carbonate; adding 2-amino-5-methylpyridine; adding o-phenylenediamine; obtaining a compound 3a; reacting 7,8-benzoquinoline with iridium trichloride hydrate to obtain a compound 4; and reacting the compound 3a with a compound 4 to obtain the 8-hydroxyquinoline derivative iridium (III) complex. The in-vitro anti-tumor activity of the compound on a human ovarian cancer drug-resistant strain SK-OV-3 / DDP is greater than that of an 8-hydroxyquinoline derivative ligand and a metal-based anti-cancer drug cis-platinum; and the toxicity to normal cells HL-7702 is very low, and a good effect of targeted inhibition of human ovarian cancer proliferation is reflected.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to an 8-hydroxyquinoline derivative iridium (III) complex and a preparation method and application thereof. Background technique [0002] Although platinum-based drugs have achieved great success in the clinical application of cancer treatment, platinum-based drugs have the disadvantages of serious toxic side effects and easy drug resistance. Therefore, medicinal chemists have been searching for atypical platinum and non-platinum drugs with high efficacy and low toxicity. 8-Hydroxyquinoline and its derivative metal complexes have attracted extensive interest of medicinal chemistry researchers in recent years due to their strong antitumor activity and diverse action mechanisms. [0003] Quinolines (quinolines) alkaloids are a class of alkaloids with a quinoline ring as the basic nucleus, such as the antimalarial drug quinine and the anticancer drug camptothecin. And 8-hydroxyquino...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61P35/00
Inventor 杨燕宾贻东廖志强农基健
Owner YULIN NORMAL UNIVERSITY
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