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A kind of preparation method and application of microwave-assisted alkyne-modified ruthenium (ii) complex

A microwave-assisted, complex technology is applied in the field of preparation of alkynyl-modified ruthenium complexes, and can solve the problems of limited ruthenium compounds and the like

Active Publication Date: 2019-01-01
GUANGDONG PHARMA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Ruthenium (II) polypyridine complexes have excellent chemical stability, redox, excited state reactivity, non-radioactive and appropriate excited state lifetime, but ruthenium compounds that can be used as nucleic acid molecular optical switches and DNA detection probes are not quite limited

Method used

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  • A kind of preparation method and application of microwave-assisted alkyne-modified ruthenium (ii) complex
  • A kind of preparation method and application of microwave-assisted alkyne-modified ruthenium (ii) complex
  • A kind of preparation method and application of microwave-assisted alkyne-modified ruthenium (ii) complex

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057]Starting ruthenium complex cis-[Ru(bpy) 2 Cl 2 ]·2H 2 O can be prepared by referring to the methods described in the literature: J.Liu, W.J.Mei, L.J.Lin, K.C.Zheng, H.Chao, F.C.Yun, L.N.Ji, Inorg.Chim.Acta (2004, 357, 285).

[0058] The synthesis of ligand p-BrPIP can be obtained with reference to the preparation method described in the following documents: J.Liu, W.J.Mei, L.J.Lin, K.C.Zheng, H.Chao, F.C.Yun, L.N.Ji, Inorg.Chim.Acta (2004, 357, 285); B.P.Sullivan, D.J.Salmon, T.J.Meyer, Inorg.Chem., (1978, 17, 3334); W.J.Mei, Y.Z.Ma, J.Liu, J.C.Chen, K.C.Zheng, L.N.Ji, J.H.Yao, Trans . Met. Chem. (2006, 31, 277).

[0059] [Ru(bpy) 2 (p-BrPIP)] (ClO 4 ) 2 Synthesis

[0060] Put cis-[Ru(bpy) into a 50ml three-neck bottle 2 Cl 2 ]·2H 2 O (105mg, 0.2mmol), p-BrPIP (113mg, 0.3mmol), 30ml ethylene glycol and water mixed solvent (volume ratio: 9:1), flow argon for 10min, heat and reflux at 120°C for 6 hours under the protection of argon After the reaction is complete...

Embodiment 2

[0062] Example 2 Microwave Synthesis of Alkyne Modified Racemic Target Compound

[0063] [Ru(bpy) 2 (p-BEPIP)] (ClO 4 ) 2 microwave assisted synthesis

[0064] Take [Ru(bpy) 2 (p-BrPIP)] (ClO 4 ) 2 120mg was added to a 30ml microwave reaction tube, 20ml of anhydrous acetonitrile and a stirrer were added, under the protection of argon, phenylacetylene (0.14ml, 1.25mmol), palladium catalyst and copper catalyst were added, sealed and placed in a microwave reactor Microwave irradiation reaction at 110°C for 15 minutes, after the reaction was completed, impurities were removed by filtration, and spin-dried under reduced pressure. The crude product was dissolved in acetonitrile, passed through a 200-300 mesh neutral alumina column, rinsed with acetonitrile, and the brown-red second color band was collected, and spin-dried under reduced pressure to obtain a brown-red solid with a yield of 89.2%. ESI-MS (in CH 3 CN, m / z) such as Figure 4 Shown: 809.3([M+H] + , calculated va...

Embodiment 3

[0069] Example 3 Microwave Synthesis of Alkyne Modified Chiral Target Compound

[0070] Chiral ruthenium complex Λ-[Ru(bpy) 2 (p-BrPIP)] 2+ , Δ-[Ru(bpy) 2 (p-BrPIP)] 2+ You can refer to the methods described in the literature: Chen T., Mei W.-J.*, Wong Y.-S., Liu J., Liu Y., Xie H.-S.and Zheng W.-J.*, Med Prepared by .Chem.Commun.(2010, 1, 73).

[0071] A-[Ru(bpy) 2 (p-BEPIP)] (ClO 4 ) 2 microwave assisted synthesis

[0072] Take A-[Ru(bpy) 2 (p-BrPIP)] (ClO 4 ) 2 120mg was added to a 30ml microwave reaction tube, 20ml of anhydrous acetonitrile and a stirrer were added, under the protection of argon, phenylacetylene (0.14ml, 1.25mmol), palladium catalyst and copper catalyst were added, sealed and placed in a microwave reactor 110°C microwave radiation reaction for 15min. After the reaction was completed, the insoluble matter was removed by filtration, and the filtrate was purified by passing through a 200-300-mesh alumina column with acetonitrile to obtain the targ...

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Abstract

The invention discloses an alkynyl-containing ruthenium (II) complex, its synthesis method and application. In the invention, the alkynyl-containing ruthenium (II) complex prepared by a microwave assisted method has a structural general formula shown as (I). The alkynyl-containing ruthenium (II) complex provided by the invention has very good results in inhibiting tumor cells. The alkynyl-containing ruthenium (II) complex has strong fluorescence emission, can interact with DNA to generate obvious fluorescence changes, and has strong adhesion with DNA, thus having potential application value in DNA fluorescence diagnostic probes and solar cell materials. Therefore, the alkynyl-containing ruthenium (II) complex provided by the invention can be used for preparing drugs for prevention or treatment of cancers. In addition, the alkynyl-containing ruthenium (II) complex can also be used for DNA fluorescence diagnostic probes and solar cells as well as photosensitizers.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry, molecular biology and molecular materials, in particular to a preparation method of an alkynyl-modified ruthenium (II) complex and its advantages as a novel complex in inhibiting tumor cells, DNA fluorescence Applications in diagnostic probes, solar cell materials. Background technique [0002] The study of ruthenium complexes as antitumor drugs has become one of the research hotspots in the fields of medicinal chemistry, chemical biology, and bioinorganic chemistry in recent years. For example, Clarke et al reviewed the anticancer activity of ruthenium complexes, especially the anti-metastatic activity (Chem.Rev., 1999,99,2511); Sava in "Metal Compounds in Cancer Therapy (metal compounds in cancer therapy)" The antimetastatic activity of ruthenium complexes is reviewed in (Chapman and Hall, edited by S P Fricker, London, 1994, 65-91). With the in-depth research on ruthenium complexes, vario...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06A61K31/695A61K31/555A61P35/00C12Q1/6816G01N21/64H01G9/20
Inventor 梅文杰王淇
Owner GUANGDONG PHARMA UNIV