Saw horse carbonyl ruthenium compound and preparation method thereof

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

Inactive Publication Date: 2013-05-08
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Saw horse carbonyl ruthenium compound and preparation method thereof
  • Saw horse carbonyl ruthenium compound and preparation method thereof
  • Saw horse carbonyl ruthenium compound and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

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

[0052] Formula Ⅰ

[0053] In formula Ⅰ: R 1 for C 6 h 5 -X, X is p-CH 3 -, R 2 It is dimethyl sulfoxide, namely DMSO, and its chemical name is double-bridged p-toluate tetracarbonyl bis(dimethyl sulfoxide) diruthenium.

[0054] The preparation method of above-mentioned sawhorse carbonyl ruthenium compound is made up of the following steps:

[0055] (1) Add 0.20g Ru 3 (CO) 12 And 0.74g compound 1 was dissolved in toluene under nitrogen protection until completely dissolved, Ru 3 (CO) 12 The molar ratio to compound 1 is 1:3.2, heated to 110°C and refluxed for 10 hours, tracked by thin layer chromatography until the raw materials are consumed, and the toluene is removed by rotary evaporation to obtain intermediate A, whose structural formula is:

[0056] Formula II

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

[0...

Embodiment 2

[0064] The general structural formula of the sawhorse carbonyl ruthenium compound of the present embodiment is formula I, and R in formula I 1 for C 6 h 5 -X, X is p-CH 3 -, R 2 For dimethyl sulfoxide, namely DMSO.

[0065] The preparation method of above-mentioned sawhorse carbonyl ruthenium compound is made up of the following steps:

[0066] (1) Add 0.20g Ru 3 (CO) 12 And 0.689g compound 1 was dissolved in toluene under nitrogen protection until completely dissolved, Ru 3 (CO) 12 The molar ratio to Compound 1 was 1:3, heated to 110°C and refluxed for 8 hours, tracked by thin-layer chromatography until the raw materials were consumed, and the toluene was removed by rotary evaporation to obtain intermediate A, whose structural formula was formula II.

[0067] (2) Dissolve intermediate A completely in tetrahydrofuran under nitrogen protection, heat to 65°C and reflux for 1 hour, cool to 25°C, add 106 μl dimethyl sulfoxide, the molar ratio of intermediate A to dimethyl ...

Embodiment 3

[0069] The general structural formula of the sawhorse carbonyl ruthenium compound of the present embodiment is formula I, and R in formula I 1 for C 6 h 5 -X, X is p-CH 3 -, R 2 For dimethyl sulfoxide, namely DMSO.

[0070] The preparation method of above-mentioned sawhorse carbonyl ruthenium compound is made up of the following steps:

[0071] (1) Add 0.20g Ru 3 (CO) 12 And 0.918g compound 1 was dissolved in toluene under nitrogen protection until completely dissolved, Ru 3 (CO) 12 The molar ratio to Compound 1 was 1:4, heated to 110°C and refluxed for 12 hours, tracked by thin-layer chromatography until the raw materials were consumed, and the toluene was removed by rotary evaporation to obtain intermediate A, whose structural formula was formula II.

[0072] (2) Dissolve intermediate A in tetrahydrofuran under nitrogen protection, heat to 65°C and reflux for 3 hours, cool to 50°C, add 213 μl dimethyl sulfoxide, the molar ratio of intermediate A to dimethyl sulfoxide...

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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 double ruthenium transition metal carbonyl compounds, and particularly relates to a sawhorse-type double ruthenium carbonyl compound with medical therapeutic effects and a preparation method thereof. Background technique [0002] Carbon monoxide (CO) is a colorless, odorless, poisonous gas that has long been considered the "silent killer" of mammals. The ability of hemoglobin in blood to bind CO is much higher than that of O 2 Excess CO saturates the oxygen-transporting protein, thereby hindering the oxygen transport of the organism, causing hypoxia in the body, and death in severe cases. However, physiological studies in recent decades have found that CO gas is constantly produced in the human body. Marks et al. found that carbon monoxide has many physiological and pathological therapeutic effects, such as anti-inflammation and anti-rejection, protection of cell apoptosis, and...

Claims

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Application Information

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Patent Type & Authority Applications(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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