Water-soluble carbon monoxide releasing molecule and its preparation method and application

A carbon monoxide, water-soluble technology, applied in chemical instruments and methods, botanical equipment and methods, applications, etc., to achieve excellent water solubility and biocompatibility, excellent controllable slow-release carbon monoxide performance, and broad-spectrum bactericidal performance

Active Publication Date: 2015-11-18
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] A technical problem to be solved by the present invention is to overcome the shortcomings of existing transition metal carbonyl compound carbon monoxide release molecules, and provide a multi-target antibacterial water-soluble carbon monoxide release molecule that combines carbon monoxide, metals and quaternary ammonium salt antibacterial activities

Method used

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  • Water-soluble carbon monoxide releasing molecule and its preparation method and application
  • Water-soluble carbon monoxide releasing molecule and its preparation method and application
  • Water-soluble carbon monoxide releasing molecule and its preparation method and application

Examples

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Effect test

Embodiment 1

[0029] Taking the preparation of the following water-soluble carbon monoxide releasing molecule as an example, the raw materials used and the preparation method are as follows:

[0030]

[0031] 1. Preparation of Formula II Compound

[0032] Under the protection of nitrogen, add 0.532g (2mmol) molybdenum hexacarbonyl and 4mL tetrahydrofuran into the Shrek reaction tube, and then add 1.5mL1.6mol / L methyl lithium ether solution, the molar ratio of molybdenum hexacarbonyl to methyl lithium is 1:1, stirred, and placed in a dry ice-acetone bath at -78°C for 60 minutes to prepare the compound of the following formula.

[0033]

[0034] 2. Preparation of water-soluble carbon monoxide releasing molecules

[0035] Add 0.84g (4mmol) tetraethylammonium bromide to the compound prepared in step 1, stir for 1 minute, distill off tetrahydrofuran under reduced pressure at room temperature, separate the product with a silica gel column at -78°C, and use dichloromethane / petroleum ether ...

Embodiment 2

[0042] Taking the preparation of the following water-soluble carbon monoxide releasing molecule as an example, the raw materials used and the preparation method are as follows:

[0043]

[0044] In the preparation of the water-soluble carbon monoxide release molecule step 2 in Example 1, the tetraethylammonium bromide used is replaced with equimolar tetramethylammonium chloride, and the other steps are the same as in Example 1 to prepare a water-soluble carbon monoxide release molecule, Its yield was 38%.

Embodiment 3

[0046] Taking the preparation of the following water-soluble carbon monoxide releasing molecule as an example, the raw materials used and the preparation method are as follows:

[0047]

[0048]In the step 2 of preparing the water-soluble carbon monoxide release molecule in Example 1, the tetraethylammonium bromide used is replaced with equimolar tetrabutylammonium bromide, and the other steps are the same as in Example 1 to prepare a water-soluble carbon monoxide release molecule. Its yield was 86%.

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Abstract

The invention discloses a water-soluble carbon monoxide releasing molecule. The structural formula of the water-soluble carbon monoxide releasing molecule is shown in the following formulaspecification, wherein M is Cr or Mo; R1, R2, R3, R4 are independently benzyl or C1-C18 alkyls, any of R1, R2, R3, and R4 is benzyl, and the rest three are independently C1-C18 alkyls; and R5 is C1-C4 alkyls or phenyls. The compound has excellent controllable carbon monoxide slow release performance, water solubility and biocompatibility and excellent antimicrobial activity, and; as as shown in experimental results, the compound expresses broad-spectrum bactericidal performance to gram-positive bacterium and gram-negative bacterium, solves the problems of water solubility and CO slow release of the existing metal carbonyl carbon monoxide releasing molecule, overcomes the limitation of single antimicrobial target of the traditional antibiotics resulting in difficulty to effectively kill a variety of bacteria, and has a broad application prospect in the antimicrobial field.

Description

technical field [0001] The invention belongs to the technical field of antibacterial small molecule compounds, and in particular relates to the preparation of a water-soluble organic metal compound with antibacterial effect. Background technique [0002] The emergence of drug-resistant bacteria has brought new challenges to human health and safety, and it is difficult for traditional antibiotics to effectively kill these bacteria with a single antibacterial target. Organometallic compounds are a class of promising multi-target antimicrobial small molecules. They not only provide organic sources of antibacterial drugs, but also may have synergistic effects with the toxic metals they contain to produce specific and highly effective antibacterial activities. At present, common metal-organic antibacterial compounds include organic arsenic compounds, N-heterocyclic carbene Ag compounds, platymycin metal-organic derivatives, penicillin and quinolone metal-organic derivatives, etc....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F11/00C07C211/63C07C209/68A61K31/28A61P31/04A01N55/00A01P1/00D21H17/12D21H21/36
Inventor 张伟强周亚青陈梦娇高培森南小平
Owner SHAANXI NORMAL UNIV
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