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Ruthenium polypyridyl complex using quinolones compound as ligand, preparation method and application thereof

A technology of ruthenium polypyridine and quinolones, which is applied in the field of metal complexes of quinolones, can solve the problems of prolonging the survival time of tumor patients, achieve good inhibition effect, improve lipid-water partition coefficient, and enhance absorption

Inactive Publication Date: 2010-06-23
GUANGDONG PHARMA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In recent years, cancer chemotherapy has made considerable progress, and the survival time of cancer patients has been significantly prolonged, especially in the treatment of leukemia and malignant lymphoma. The treatment of the above solid tumors has not yet achieved satisfactory results

Method used

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  • Ruthenium polypyridyl complex using quinolones compound as ligand, preparation method and application thereof
  • Ruthenium polypyridyl complex using quinolones compound as ligand, preparation method and application thereof
  • Ruthenium polypyridyl complex using quinolones compound as ligand, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 [Ru(bpy) with ofloxacin (Ofloxacin) as a ligand 2 Preparation of OFLX]Cl

[0030]

[0031] 1.1 cis-[Ru(bpy) 2 Cl 2 ]·2H 2 Synthesis of O

[0032] Ruthenium trichloride (RuCl 3 ·nH 2 O) (1.56g, 6mmol), bipyridine (1.87g, 12mmol) and lithium chloride (2.42g, 57.6mmol), were dissolved in 15ml of DMF, and heated to reflux for 8 hours under the protection of argon. Cool to room temperature, add 50ml of acetone, shake well, and freeze overnight in the refrigerator. After filtration, purple-black microcrystals were obtained, which were washed with ice water until nearly colorless, and dried, with a yield of 71.0% (calculated as bipyridine).

[0033] 1.2 [Ru(bpy) 2 Preparation of OFLX]Cl

[0034] Add cis-[Ru(bpy) to the 100ml three-necked bottle 2 ] Cl 2 2H 2 O (104mg, 0.2mmol), ofloxacin (100mg 0.3mmol), sodium ethoxide (34mg, 0.5mmol), 50ml of absolute ethanol were stirred and dissolved, refluxed at 100°C for 3h under the protection of argon, and an e...

Embodiment 2

[0036] Example 2 [Ru(phen) with ofloxacin (Ofloxacin) as a ligand 2 Preparation of OFLX]Cl

[0037]

[0038] 2.1 cis-Ru(phen) 2 Cl 2 2H 2 Synthesis of O

[0039] RuCl 3 ·nH 2 O, phenanthroline (2.16g, 12mmol), LiCl (1.68g, 28mmol), DMF (10ml) was added, and refluxed under the protection of argon for 8 hours. After the reactant was cooled to room temperature, acetone (50 ml) was added to the reactant and frozen overnight to obtain purple crystals. Washed with cold water and acetone, and dried in vacuum, the yield was 72%.

[0040] 2.2 [Ru(phen) 2 Preparation of OFLX]Cl

[0041] Add cis-[Ru(phen) 2 ] Cl 2 2H 2O (113mg, 0.2mmol), ofloxacin (100mg, 0.3mmol), sodium ethoxide (34mg, 0.5mmol), and 50ml of absolute ethanol were stirred and dissolved, and returned to 100°C for 3h under the protection of argon. After the reaction was completed, an equivalent amount of Remove excess sodium ethoxide with hydrochloric acid, spin dry to recover the solvent, dissolve the obta...

Embodiment 3

[0043] Example 3 [Ru(dmbpy) with ofloxacin (Ofloxacin) as a ligand 2 Preparation of OFLX]Cl

[0044]

[0045] 3.1 cis-[Ru(dmbpy) 2 Cl 2 ]·2H 2 Synthesis of O

[0046] Ruthenium trichloride (RuCl 3 ·nH 2 O) (1.56g, 6mmol), 4,4'-dimethyl-2,2'-bipyridine (2.21g, 12mmol) and LiCl (2.42g, 57.6mmol) in 15ml DMF, argon Heating to reflux under air protection for 8 hours. Cool to room temperature, add 50ml of acetone, shake well, and freeze overnight in the refrigerator. Filtrate to obtain purple-black microcrystals, wash with ice water until nearly colorless, and dry, with a yield of 70.0% (calculated as bipyridine).

[0047] 3.2 [Ru(dmbpy) 2 Preparation of OFLX]Cl

[0048] Add cis-[Ru(dmbpy) to the 100ml three-necked bottle 2 ] Cl 2 2H 2 O (115mg, 0.2mmol), ofloxacin (100mg, 0.3mmol), sodium ethoxide (34mg, 0.5mmol), and 50ml of absolute ethanol were stirred and dissolved, and refluxed at 100°C for 3h under the protection of argon. After the reaction was completed, an...

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Abstract

The invention discloses a ruthenium polypyridyl complex using quinolones compound as ligand, a preparation method and application thereof. The constitutional formula of the complex is as shown in a formula (I), wherein R1 denotes alkyl, substituted alkyl, naphthenic base, substituted naphthenic base, aryl or substituted aryl; R2 denotes ethyl or cyclopropyl; R3 denotes hydrogen or amido; R4 denotes hydrogen, fluorine, chlorine, cyan or amido; R5 denotes methyl, piperazinyl, cyclopentylamino, dimethylamino, methyl, halogen or hydrogen; R6 denotes hydrogen, fluorine or forms a hexatomic ring together with R1 through carbon atoms and oxygen atoms in a bonding way; R7 denotes hydrogen or methyl; R8 and R9 denote hydrogen or form a benzene ring through carbon atoms in a bonding way; and X and Y denote carbon atoms or nitrogen atoms. The invention uses quinolones compound as ligand and ruthenium polypyridyl group as active group to prepare medicine for curing tumors or antibacterial medicine, and has good antibacterial effect and bacteriostatic effect. Formula (1) is shown as the accompanying drawing.

Description

technical field [0001] The invention relates to the field of metal complexes of quinolone compounds, in particular to a ruthenium polypyridine complex with quinolone compounds as ligands and its preparation method and application. Background technique [0002] Cancer mortality in my country ranks second among all diseases, and there are 1.6 to 1.7 million new cancer patients every year. Therefore, the demand for new anti-tumor drugs is constantly increasing. According to the statistics of the Ministry of Health, the annual sales of anti-tumor drugs will increase to 60 billion US dollars by 2010, with an annual growth rate of more than 10%. In recent years, cancer chemotherapy has made considerable progress, and the survival time of cancer patients has been significantly prolonged, especially in the treatment of leukemia and malignant lymphoma. The treatment of the above solid tumors has not yet achieved satisfactory results. [0003] Quinolones, also known as pyruvate or p...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61K31/5383A61K31/496A61P35/00A61P31/04
Inventor 梅文杰黄东纬尹鹏
Owner GUANGDONG PHARMA UNIV
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