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Chiral platinum complex and preparation method thereof

A platinum complex and chiral technology, applied in the application field of chiral platinum complexes and their preparation, and preparation of anti-tumor drugs, achieving strong anti-tumor activity, great application potential, and simple synthesis methods

Inactive Publication Date: 2015-04-22
YULIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far most of the small molecules that stabilize G-quadruplex DNA are organic compounds, and only a small part are metal complexes

Method used

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  • Chiral platinum complex and preparation method thereof
  • Chiral platinum complex and preparation method thereof
  • Chiral platinum complex and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] One, preparation method of the present invention:

[0040](1) Preparation of compound 2: Weigh 2 mol of phenanthroline-5,6-dione (compound 1) and 2 mol of 2-hydroxy-4-methoxybenzaldehyde, add glacial acetic acid 16mL and ammonium acetate 3.1 g, under 120°C oil bath, heat to reflux for 6h, cool to room temperature; under ice bath conditions, stir, slowly add 16mL of concentrated ammonia water (25-28%) to neutrality to obtain 2-[2-(hydroxyl) - yellow precipitate of 4-(methoxy)-phenyl]imidazo[4,5-f][1,10]-phenanthroline (compound 2);

[0041] (2) Preparation of complex 3: Prepare potassium chloroplatinite solution in advance, add 0.8mL water to 2.4mmol potassium chloroplatinite, heat to dissolve at 60°C, add 2mL dimethyl sulfoxide, heat and stir at 60°C for 5min That's it.

[0042] Add 10mL of dimethyl sulfoxide to 2.4mmol of compound 2, heat the oil bath to 140°C to dissolve compound 2, slowly drop the pre-prepared potassium chloroplatinite solution into the compound 2 ...

Embodiment 2

[0064] One, preparation method of the present invention:

[0065] (1) Preparation of compound 2: Weigh 2 mol of phenanthroline-5,6-dione (compound 1) and 4 mol of 2-hydroxy-4-methoxybenzaldehyde, add glacial acetic acid 20mL and ammonium acetate 3.6 g, in an oil bath at 130°C, heat to reflux for 7 hours, and cool to room temperature; in an ice bath, stir, and slowly add 20 mL of concentrated ammonia water (25-28%) dropwise to neutral, and a yellow precipitate (compound 2) is obtained;

[0066] (2) Preparation of complex 3: Prepare potassium chloroplatinite solution in advance, add 1 mL of water to 2.4 mmol potassium chloroplatinite, heat to dissolve at 50 ° C, add 3 mL of dimethyl sulfoxide, heat and stir at 50 ° C for 10 min Can.

[0067] Add 12mL of dimethyl sulfoxide to 2.4mmol of compound 2, heat the oil bath to 150°C to dissolve compound 2, slowly drop the pre-prepared potassium chloroplatinite solution into the compound 2 solution, and a yellow precipitate precipitates ...

Embodiment 3

[0083] One, preparation method of the present invention:

[0084] (1) Preparation of compound 2: Weigh 2 mol of phenanthroline-5,6-dione (compound 1) and 4 mol of 2-hydroxy-4-methoxybenzaldehyde, add glacial acetic acid 18mL and ammonium acetate 3.6 g, in an oil bath at 125°C, heated to reflux for 5h, cooled to room temperature; in an ice bath, stirred, and slowly added 18mL of concentrated ammonia water (25-28%) dropwise until neutral, and a yellow precipitate (compound 2) was obtained;

[0085] (2) Preparation of complex 3: Prepare potassium chloroplatinite solution in advance, add 1 mL of water to 2.4 mmol potassium chloroplatinite, heat to dissolve at 55 ° C, add 2.5 mL of dimethyl sulfoxide, heat and stir at 55 ° C for 8 min That's it.

[0086] Add 11mL of dimethyl sulfoxide to 2.4mmol of compound 2, heat the oil bath to 145°C to dissolve compound 2, slowly drop the pre-prepared potassium chloroplatinite solution into the compound 2 solution, and a yellow precipitate pre...

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Abstract

The invention discloses a chiral platinum complex and a preparation method thereof. The complex, namely dichloride-2-[2-(hydroxyl)-4-(methoxyl)-phenyl] imidazo[4,5-f][1,10]-phenanthroline.S, S-cyclohexanediamine platinum (II) has chirality. The preparation method comprises the following steps: preparing 2-[2-(hydroxyl)-4-(methoxyl)-phenyl] imidazo[4,5-f][1,10]-phenanthroline by taking 1,10-phenanthroline-5,6-dione and 2-hydroxyl-4-methoxybenzaldehyde as raw materials; adding potassium chloroplatinite to prepare 2-[2-(hydroxyl)-4-(methoxyl)-phenyl] imidazo[4,5-f][1,10]-phenanthroline.platinum (II) dichloride; finally adding cyclohexanediamine, thereby obtaining the chiral platinum complex disclosed by the invention. The complex has the characteristic of excellent anti-tumor activity, and can be applied to drugs resistant to the liver cancer, the lung cancer and the gastric cancer.

Description

technical field [0001] The invention relates to the field of anti-tumor molecular compounds, in particular to a chiral platinum complex, a preparation method thereof and an application in the preparation of anti-tumor drugs. Background technique [0002] Since the discovery of G-quadruplex DNA as a potential antitumor target, a great deal of work has been done on small organic molecules that can stabilize G-quadruplex DNA. But so far most of the small molecules that stabilize G-quadruplex DNA are organic compounds, and only a small part are metal complexes. Because metal complexes have many incomparable advantages of small organic molecules, such as rigid and flexible geometric structure changes and rich electrochemical properties, they also have optical, magnetic and catalytic properties. In terms of binding mode, metal complexes can not only interact with G-quadruplex DNA through π-π stacking, but also stabilize the G-quadruplex structure by forming covalent bonds with ba...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61P35/00
CPCC07F15/0093
Inventor 杨燕罗旭健黎昌贵
Owner YULIN NORMAL UNIVERSITY
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