Alkane chain or substituted alkane chain modified ruthenium complex and preparation method and application thereof

A ruthenium complex and alkane chain technology, which is applied in the field of alkane chain or substituted alkane chain modification of ruthenium complex and its preparation, can solve the problems of poor solubility, large toxic and side effects, etc., and achieves improved absorption capacity and improved transmembrane absorption capacity. , the effect of enhancing lipophilicity

Active Publication Date: 2020-09-25
GUANGDONG PHARMA UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The clinical treatment of tumors is mainly by chemotherapy, but currently used chemotherapy drugs such as cisplatin, etc., still have problems such as large toxic side effects and poor solubility.

Method used

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  • Alkane chain or substituted alkane chain modified ruthenium complex and preparation method and application thereof
  • Alkane chain or substituted alkane chain modified ruthenium complex and preparation method and application thereof
  • Alkane chain or substituted alkane chain modified ruthenium complex and preparation method and application thereof

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preparation example Construction

[0064] The present invention provides a method for preparing the alkane chain or substituted alkane chain modified ruthenium complex described in the above scheme, comprising the following steps:

[0065] The ruthenium raw material, R 1 -Br, potassium carbonate and an organic solvent are mixed to carry out a substitution reaction to obtain an alkane chain or a substituted alkane chain modified ruthenium complex having a structure shown in formula I;

[0066] Wherein, the ruthenium raw material has a structure shown in formula II:

[0067]

[0068] In the present invention, in the ruthenium raw material having the structure shown in formula II, L, R 2 , R 3 and R 4 It is preferably consistent with the corresponding group in formula I, R 1 -R in Br 1 Preferably, it is consistent with the corresponding group in formula I, and will not be repeated here.

[0069] In the present invention, the source of the ruthenium raw material is not particularly limited, and can be obta...

Embodiment 1

[0089] Prepare ruthenium raw material, comprise the following steps:

[0090]

[0091] [RuL 2 Cl 2 ]·2H 2 O (105mg, 0.2mmol, wherein, L is o-phenanthroline group), ligand (0.4mmol, wherein, R 2 for-CF 3 , R 3 and R 4 is hydrogen), a mixed solvent of ethylene glycol and water (V 乙二醇 :V 水 =9:1), join in the three-necked bottle, and heat the oil bath to reflux at 120°C for 6h;

[0092] After the reaction, cool to room temperature (25°C), dilute the obtained system with water, filter, take the filtrate and add excess sodium persulfate to produce an orange solid, filter with suction, and dry the filter cake to obtain a crude product; the crude product is dissolved in acetonitrile and removed by filtration. Insoluble ligand, filtrate carries out neutral alumina column chromatography, with the mixed solution of acetonitrile and toluene (V 乙腈 :V 甲苯 =2:1) ​​was used as the eluent for rinsing, and the eluate of the first band was collected; spin-dried, dissolved in acetonit...

Embodiment 2

[0098] The ruthenium raw material is prepared according to the method of Example 1, the difference is that in the ligand used, R 3 for-CF 3 , R 2 and R 4 is hydrogen, and the obtained ruthenium raw material is recorded as compound RPL082;

[0099] According to the method of Example 1, compound RPL082 is used to prepare a compound having the structure shown in formula 2, which is denoted as compound 2 (RPL082-BBr, and the ESI-MS spectrum is as follows figure 2 shown), the reaction scheme is as follows:

[0100]

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Abstract

The invention provides an alkane chain or substituted alkane chain modified ruthenium complex and a preparation method and application thereof, and belongs to the technical field of medicinal chemistry. According to the invention, alkyl or halogenated alkyl is introduced into the structure of the polypyridine ruthenium complex, the lipophilicity of the polypyridine ruthenium complex is enhanced, the transmembrane absorption ability is improved, such that the obtained alkane chain or substituted alkane chain modified ruthenium complex can easily enter the cells, the absorption ability is substantially improved, the efficient and low-toxicity effect can be achieved by reducing the dosage, and the great potential application prospect is provided in the preparation of efficient and low-toxicity cancer treatment and/or prevention drugs.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to an alkane chain or substituted alkane chain modified ruthenium complex and a preparation method and application thereof. Background technique [0002] Malignant tumor is one of the important diseases that threaten people's health. It has always been a difficult problem that people are overcoming, and certain research results have been obtained in the long process of overcoming it. Chemotherapy is the main method of clinical tumor treatment, but currently used chemotherapeutic drugs such as cisplatin still have problems such as large toxic side effects and poor solubility. Therefore, the research and development of new antitumor drugs has great practical significance for protecting people's health. [0003] Among the metal complexes with anti-tumor activity, ruthenium complexes have received extensive attention. It is generally believed internationally that ruthenium ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61P35/00A61K31/555
CPCC07F15/0053A61P35/00C07B2200/13
Inventor 梅文杰
Owner GUANGDONG PHARMA UNIV
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