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Phenanthroline-based carbonyl manganese compound as well as preparation method and application thereof

A carbonyl manganese compound and phenanthroline technology, applied in the field of medicinal chemistry, can solve the problems of poor carbon monoxide release effect and the like, and achieve the effect of high reaction yield

Active Publication Date: 2020-10-02
JIAXING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the light sources required for the light-induced production of carbon monoxide in the existing carbonyl manganese compound carbon monoxide release agents are ultraviolet light, but the effect on the release of carbon monoxide induced by visible light or near-infrared light is poor

Method used

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  • Phenanthroline-based carbonyl manganese compound as well as preparation method and application thereof
  • Phenanthroline-based carbonyl manganese compound as well as preparation method and application thereof
  • Phenanthroline-based carbonyl manganese compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] A manganese carbonyl compound based on o-phenanthroline has a structure as shown in formula (I),

[0025]

[0026] The specific preparation method of the above-mentioned formula (I) based on the manganese carbonyl compound of o-phenanthroline is as follows:

[0027] Phenylimidazo[5,6-f]phenanthroline (133mg, 0.45mmol), a ligand of formula (II), was placed in dichloromethane (26.2g) and heated under reflux, and the reaction bottle was wrapped with tin foil. Protect from light, add Mn(CO) after the solution is refluxed 5 Br (124mg, 0.45mmol), a large amount of yellow precipitates were produced after 0.5h of reaction, the mixed solution continued to reflux for 2h, then placed in a refrigerator to cool, and finally suction filtered to produce a yellow powdery solid (200mg, yield 80% ), to obtain formula (I) based on the manganese carbonyl compound of o-phenanthroline;

[0028] Its synthetic route is as follows:

[0029]

[0030] 1 H NMR (400MHz, DMSO): 9.47(d, J=4...

Embodiment 2

[0032] A manganese carbonyl compound based on o-phenanthroline has a structure as shown in formula (I),

[0033]

[0034] The specific preparation method of the above-mentioned formula (I) based on the manganese carbonyl compound of o-phenanthroline is as follows:

[0035] Put phenylimidazo[5,6-f]phenanthroline (133mg, 0.45mmol), a ligand of formula (II), in dichloromethane (53.2g) and heat under reflux, and wrap the reaction bottle with tinfoil Protect from light, add Mn(CO) after the solution is refluxed 5 Br (124mg, 0.45mmol), a large amount of yellow precipitates were produced after 1h of reaction, the mixed solution continued to reflux for 2h, then placed in a refrigerator to cool, and finally suction filtered to obtain a yellow powdery solid, that is, formula (I) based on Manganese carbonyl compounds of o-phenanthroline;

[0036] Its synthetic route is as follows:

[0037]

[0038] In order to illustrate the performance of the manganese carbonyl compound based o...

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PUM

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Abstract

The invention discloses a phenanthroline-based carbonyl manganese compound, which belongs to the technical field of medical chemistry and has a structure shown as a formula (I). The invention furtherdiscloses a preparation method and application of the phenanthroline-based carbonyl manganese compound. According to the preparation method, a phenanthroline derivative ligand with a relatively largeconjugated system is selected to react with manganese pentacarbonyl bromide to obtain a corresponding carbonyl manganese compound, the compound can be decomposed to release carbon monoxide under the action of visible light (LED blue light), the defect that a carbonyl manganese compound generates carbon monoxide under the action of ultraviolet light through induction is overcome, and carbon monoxide release induced by visible light is achieved. The structure shown as the following formula (I) is shown in the specification.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and specifically relates to a manganese carbonyl compound based on o-phenanthroline, a preparation method and an application. Background technique [0002] Carbon monoxide (CO) is a deadly toxic gas, but in 1991, Mark et al. found that CO has important physiological functions in living organisms. This is the second gas messenger molecule discovered after NO, and it is also a neuron Transmitter. Studies have found that carbon monoxide, as a cell messenger molecule, has various physiological effects such as relaxing blood vessels and bronchial smooth muscle, inhibiting platelet aggregation, inhibiting inflammation, anti-oxidation, anti-apoptosis, and anti-proliferation in vivo. It also plays an important role in regulating physiological processes and inhibiting pathological processes such as acute lung injury, organ ischemia-reperfusion injury, and organ transplant rejection. Animal e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F13/00A61P9/08A61P7/02A61P11/00A61P29/00A61P39/06A61P35/00A61P25/00A61P9/10A61P37/06
CPCC07F13/005A61P9/08A61P7/02A61P11/00A61P29/00A61P39/06A61P35/00A61P25/00A61P9/10A61P37/06
Inventor 姜秀娟李爱云吴晓君李菲潘滢滢刘小明
Owner JIAXING UNIV
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