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Application of imidazole [4,5-f][1,10] phenanthroline and derivative thereof to preparation of antineoplastic drug

An anti-tumor drug, 5-f technology, applied in the direction of anti-tumor drugs, drug combinations, pharmaceutical formulations, etc., to achieve the effects of inhibiting the occurrence and development, significant curative effect, and good medicinal prospects

Inactive Publication Date: 2010-06-16
GUANGDONG PHARMA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no specific research on the antitumor activity of imidazo[4,5-f][1,10]phenanthroline and its derivatives, so it is worth further exploring

Method used

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  • Application of imidazole [4,5-f][1,10] phenanthroline and derivative thereof to preparation of antineoplastic drug
  • Application of imidazole [4,5-f][1,10] phenanthroline and derivative thereof to preparation of antineoplastic drug
  • Application of imidazole [4,5-f][1,10] phenanthroline and derivative thereof to preparation of antineoplastic drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The preparation of embodiment 1 imidazo[4,5-f][1,10]phenanthroline

[0026] 0.52g (2.4mmol) of phenanthroline 5,6-diketone, 0.072g (2.4mmol) of formaldehyde, 3.8g of ammonium acetate, and 30ml of glacial acetic acid were heated to 110°C for 4 hours in a 50ml round bottom flask, and the reaction mixture was After cooling to room temperature, add 40ml of distilled water and concentrated ammonia water to adjust the pH to 7 to obtain a yellow flocculent precipitate; filter with suction, wash with water, and dry at 50°C. After dissolving in absolute ethanol, pass through a 60-100 mesh silica gel column, rinse with absolute ethanol to obtain a light yellow solution, and spin dry under reduced pressure to obtain a light yellow solid, which is recrystallized from absolute ethanol with a yield of 87%. Calculated for C 13 h 8 N 4 ·H 2 O (%): C: 65.5; H: 3.36; N: 23.5; ESI-MS (in MeOH, m / z): 238.4.

Embodiment 2

[0027] Example 2 Preparation of 2-(2-trifluoromethylphenyl)imidazo[4,5-f][1,10]phenanthroline

[0028] 0.52g (2.4mmol) of phenanthroline 5,6-dione, 0.42g (2.4mmol) of 2-trifluoromethylbenzaldehyde, 3.8g of ammonium acetate, and 30ml of glacial acetic acid were heated to reflux at 110°C in a 50ml round bottom flask After 4 hours, after the reaction mixture was cooled to room temperature, 40 ml of water was added, and concentrated ammonia water was added to adjust the pH to 7 to obtain a yellow flocculent precipitate; suction filtered, washed with water, and dried at 50°C. After dissolving in absolute ethanol, pass through a 60-100 mesh silica gel column, rinse with absolute ethanol to obtain a light yellow solution, and spin dry under reduced pressure to obtain a light yellow solid, which is recrystallized from absolute ethanol with a yield of 84%. Elemental analysis results (%): C: 63.0; H: 2.91; N: 14.3; ESI-MS (in MeOH, m / z): 364.4.

Embodiment 3

[0029] Example 3 Preparation of 2-(3-hydroxy-4-methoxyphenyl)imidazo[4,5-f][1,10]phenanthroline

[0030] 0.52g (2.4mmol) of phenanthroline 5,6-diketone, 0.36g (2.4mmol) of 3-hydroxy-4-methoxybenzaldehyde, 3.8g of ammonium acetate, and 30ml of glacial acetic acid were heated to 110 in a 50ml round bottom flask Reflux at °C for 4 hours. After the reaction mixture is cooled to room temperature, add 40ml of water and concentrated ammonia water to adjust the pH to 7 to obtain a yellow flocculent precipitate; filter with suction, wash with water, and dry at 50°C. After dissolving in absolute ethanol, pass through a 60-100 mesh silica gel column, rinse with absolute ethanol to obtain a light yellow solution, and spin dry under reduced pressure to obtain a light yellow solid, which is recrystallized from absolute ethanol with a yield of 79%. Elemental analysis results (%): C: 73.3; H: 4.6; N: 17.1; ESI-MS (in MeOH, m / z): 326.5.

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Abstract

The invention discloses an application of an imidazole [4,5-f][1,10] phenanthroline and a derivative thereof to the preparation of an antineoplastic drug. The structural formula of the imidazole [4,5-f][1,10] phenanthroline is as shown in formula I: wherein R is selected from components of hydrogen, C1-6 alkyl or C1-6 substituted alkyl, phenyl or substituted phenyl, pyridyl or substituted pyridyl, furyl or substituted furyl, pyrrolyl or substituted pyrrolyl, or thiazolyl or substituted thiazolyl. The imidazole [4,5-f][1,10] phenanthroline and the derivative thereof are used for preparing the antineoplastic drug and have remarkable inhibiting effect on tumor cells.

Description

technical field [0001] The invention relates to the application field of chemical drugs, in particular to the application of imidazo[4,5-f][1,10]phenanthroline and its derivatives in the preparation of antitumor drugs. Background technique [0002] Imidazo[4,5-f][1,10]phenanthroline and its substituted derivatives are excellent metal chelating reagents, which are often used as ligands to prepare various metal complexes with antitumor activity. Especially ruthenium polypyridine complexes. Wu Jianzhong et al. reported imidazo[4,5-f][1,10]phenanthroline, 2-phenylimidazol[4,5-f][1,10]phenanthroline, 2-(4-chlorophenyl ) imidazo[4,5-f][1,10]phenanthroline, 2-(4-hydroxyphenyl)imidazol[4,5-f][1,10]phenanthroline, 2-(4-nitro phenyl)imidazo[4,5-f][1,10]phenanthroline and its ruthenium complexes, and studied their ability to recognize DNA molecules (Polyhedron, 16(1), 103-107, 1997) . Mei reported the preparation of 2-(4-methoxyphenyl)imidazo[4,5-f][1,10]phenanthroline (Inorganica ...

Claims

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Application Information

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IPC IPC(8): C07D471/14A61K31/4375A61K31/444A61P35/00
Inventor 梅文杰孙冬冬
Owner GUANGDONG PHARMA UNIV
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