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Human ovarian cancer cell inhibitor as well as preparation method and application thereof

A technology of ovarian cancer cells and inhibitors, which is applied in the field of medicine to achieve the effect of targeted inhibition of human ovarian cancer proliferation and high anti-tumor activity

Active Publication Date: 2021-04-16
YULIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the 8-hydroxyquinoline derivative iridium (Ⅲ) complex has not been reported as an inhibitor of human ovarian cancer cells

Method used

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  • Human ovarian cancer cell inhibitor as well as preparation method and application thereof
  • Human ovarian cancer cell inhibitor as well as preparation method and application thereof
  • Human ovarian cancer cell inhibitor as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] (1) Human ovarian cancer cell inhibitor [Ir(3a)(BQ) 2 ] preparation and characterization:

[0040] Such as Figure 6 As shown, weigh compound 4 and compound 3a (8-hydroxyquinoline derivative) according to the molar ratio of 1:1.3, 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 the inhibitor of human ovarian cancer cells. Agent [Ir(3a)(BQ) 2 ], that ...

Embodiment 2

[0052] Human Ovarian Cancer Cell Inhibitor [Ir(3a)(BQ) 2 ] The synthetic route such as Figure 6 Shown:

[0053] (1) Preparation of Compound 1: Add 600mL of concentrated hydrochloric acid (pre-placed in the refrigerator to freeze, concentrated hydrochloric acid concentration is 37% mass fraction) and 14.5g of 8-hydroxyquinoline in a 1L round bottom flask, and heat 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-dichloroquinoline-5 ,8-diketone, denoted as c...

Embodiment 3

[0059] Human Ovarian Cancer Cell Inhibitor [Ir(3a)(BQ) 2 ] The synthetic route such as Figure 6 Shown:

[0060] (1) Preparation of compound 1: carefully add 725mL of concentrated hydrochloric acid (pre-placed in the refrigerator to freeze, the concentration of concentrated hydrochloric acid is 35% mass fraction) and 14.5g of 8-hydroxyquinoline into a 1L round bottom flask, and heat to 45°C , 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-dichloroquinoline-5 ,8-di...

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PUM

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Abstract

The invention discloses a human ovarian cancer cell inhibitor as well as a preparation method and application thereof, and belongs to the field of medicines. The chemical name of the compound is hexafluorophosphorylate.2,12,13-trimethylpyrido[3, 2-a]pyrido[1',2':1,2]imidazo[4, 5-c]phenazine.bis-benzoquinolineiridium (III). The preparation method comprises the following steps: reacting 8-hydroxyquinoline with hydrochloric acid and NaClO3; adding anhydrous potassium carbonate; adding 2-amino-5-methyl pyridine; adding 4,5-dimethyl o-phenylenediamine to prepare 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 human ovarian cancer cell inhibitor. 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 8hydroxyquinoline derivative ligand and a metal-based anti-cancer drug cis-platinum; 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 field of medical technology, in particular to an inhibitor of human ovarian cancer cells, a preparation method and an application thereof. Background technique [0002] At present, about 52,000 women in my country are diagnosed with ovarian cancer every year, and about 22,000 people die of ovarian cancer. In the past 10 years, the incidence of ovarian cancer has shown a younger trend. Ovarian cancer has the characteristics of easy proliferation and high invasiveness, which is the main reason for the failure of clinical treatment. Therefore, inhibiting the proliferation and invasion of ovarian cancer cells is one of the key points and difficulties in the treatment of ovarian cancer. [0003] 8-Hydroxyquinoline derivatives are intermediates of various drugs (such as quiniodoform, clioquinoline, etc.), and have a wide range of pharmacological activities, such as anti-cancer, anti-AIDS, anti-fungal, anti-schistosomiasis, anti-o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61K31/555A61P35/00
Inventor 杨燕宾贻东廖志强农基健
Owner YULIN NORMAL UNIVERSITY
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