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Sawhorse carbonyl ruthenium compound and preparation method thereof

A technology of sawhorse carbonyl ruthenium and compounds, which is applied in the field of sawhorse-type bisruthenium carbonyl compounds and their preparation, can solve the problems of difficult derivatization of complex structures, difficulty in controllable targeted transmission, and difficulty in targeted release, etc. The effect of increasing the bonding strength, increasing the CO release rate, and increasing the water solubility

Inactive Publication Date: 2016-05-04
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] Although the transition metal carbonyl compounds disclosed above have achieved good results in biological applications, the inventors found in the research and development process that the above-mentioned technology still has the problem of difficult controllable and targeted delivery in the process of releasing CO, and The mononuclear divalent ruthenium carbonyl compound CO-RM2 and its glycine chelate analog CO-RM3 are difficult to exist stably under complex physiological conditions, and the structure of the complex is not easy to derivate, so it is difficult to achieve targeted release. It is a ruthenium carbonyl release molecule Bottlenecks in Drug Therapy Application

Method used

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  • Sawhorse carbonyl ruthenium compound and preparation method thereof
  • Sawhorse carbonyl ruthenium compound and preparation method thereof
  • Sawhorse carbonyl ruthenium compound and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] The general structural formula of sawhorse carbonyl ruthenium compound is:

[0052] Formula I

[0053] In formula I: R 1 Is C 6 H 5 -X, X is p-CH 3 -, R 2 It is dimethyl sulfoxide, or DMSO, chemically named as double bridged p-toluic acid tetracarbonyl bis(dimethyl sulfoxide) diruthenium.

[0054] The preparation method of the above saw horse carbonyl ruthenium compound consists of the following steps:

[0055] (1) Add 0.20gRu 3 (CO) 12 And 0.74g of compound 1 dissolved in toluene under the protection of nitrogen until completely dissolved, Ru 3 (CO) 12 The molar ratio with compound 1 is 1:3.2, heated to 110°C and refluxed for 10 hours, TLC traces until the raw material is consumed, and the toluene is removed by rotary evaporation to obtain Intermediate A. Its structural formula is:

[0056] Formula Ⅱ

[0057] The molecular formula of the above compound 1 is R 1 CO 2 , R 1 Is C 6 H 5 -X, X is p-CH 3 -.

[0058] (2) Under the protection of nitrogen, completely dissolve Intermediat...

Embodiment 2

[0064] The general structural formula of the sawhorse carbonyl ruthenium compound in this embodiment is formula I, where R is 1 Is C 6 H 5 -X, X is p-CH 3 -, R 2 It is dimethyl sulfoxide, or DMSO.

[0065] The preparation method of the above saw horse carbonyl ruthenium compound consists of the following steps:

[0066] (1) Add 0.20gRu 3 (CO) 12 And 0.689g of compound 1 dissolved in toluene under the protection of nitrogen to completely dissolve, Ru 3 (CO) 12 The molar ratio with compound 1 is 1:3, heated to 110°C and refluxed for 8 hours, TLC traces until the raw material is consumed, and the toluene is removed by rotary evaporation to obtain Intermediate A with the structural formula II.

[0067] (2) Under the protection of nitrogen, completely dissolve Intermediate A in tetrahydrofuran, heat to 65°C and reflux for 1h, cool to 25°C, add 106μl dimethyl sulfoxide, the molar ratio of intermediate A to dimethyl sulfoxide is 1: 1.5, the reaction was stirred for 3 hours, and the tetrahyd...

Embodiment 3

[0069] The general structural formula of the sawhorse carbonyl ruthenium compound in this embodiment is formula I, where R is 1 Is C 6 H 5 -X, X is p-CH 3 -, R 2 It is dimethyl sulfoxide, or DMSO.

[0070] The preparation method of the above saw horse carbonyl ruthenium compound consists of the following steps:

[0071] (1) Add 0.20gRu 3 (CO) 12 And 0.918g of compound 1 dissolved in toluene under the protection of nitrogen until completely dissolved, Ru 3 (CO) 12 The molar ratio with compound 1 is 1:4, heated to 110°C and refluxed for 12 hours, TLC traces until the raw materials are consumed, and the toluene is removed by rotary evaporation to obtain Intermediate A with the structural formula II.

[0072] (2) Dissolve Intermediate A in tetrahydrofuran under the protection of nitrogen, heat to 65°C and reflux for 3h, cool to 50°C, add 213μl dimethyl sulfoxide, the molar ratio of intermediate A to dimethyl sulfoxide is 1:3 , The reaction was stirred for 2h, and the tetrahydrofuran was ...

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Abstract

The invention relates to a saw horse carbonyl ruthenium compound which is a carboxylic acid group and an axial 2 electronic ligand through connecting a bridging on a double-ruthenium tetracarbonyl saw horse skeleton structure, the bridged carboxylic acid group is coordinated with metal ruthenium through O, the bond strength of Ru-Co is improved by utilizing center metal Ru (I) with low price, the saw horse carbonyl ruthenium compound has good stability under physiological conditions and is beneficial to target release, CO release is controllable, and the water solubility of molecular and the CO release speed can be improved by changing bridging carboxylic acid group R1CO2 and the axial 2 electronic ligand, so that the saw horse carbonyl ruthenium compound can be functionalized efficiently and is easy to derive. The synthetic process is simpler and easy to obtain, and an efficient functionalization method for saw horse carbonyl ruthenium is provided.

Description

Technical field [0001] The invention belongs to the technical field of research on sawhorse type diruthenium transition metal carbonyl compounds, and particularly relates to a sawhorse type diruthenium carbonyl compound with medical treatment effect and a preparation method thereof. Background technique [0002] Carbon monoxide (CO) is a colorless, odorless, toxic gas, and has always been considered a "silent killer" of mammals. The binding ability of hemoglobin and CO in the blood is much higher than that of O 2 With its binding capacity, excess CO saturates the protein that transports oxygen, thereby hindering the oxygen transport of the organism, causing the body to hypoxia, and in severe cases leading to death. However, physiological studies in recent decades have found that CO gas is always produced in the human body. Marks and other studies have found that carbon monoxide has many physiological and pathological therapeutic effects, such as anti-inflammatory and anti-reject...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C07H1/00C07H3/02C07H3/04C08G65/48C08B31/00C07K5/062C07K7/06A61P35/00
Inventor 张伟强南小平周亚青陈梦娇朱润军
Owner SHAANXI NORMAL UNIV
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