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Photo-induced manganese carbonyl compound carbon monoxide releasing agent as well as preparation method and application thereof

A carbonyl compound and carbon monoxide technology, which is applied in the field of light-induced manganese carbonyl compound carbon monoxide release agent and its preparation, can solve the problems of high energy, weak skin penetration ability, harmful to the body, etc., and achieve the effect of high reaction yield

Pending Publication Date: 2021-06-04
JIAXING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, most light-induced manganese carbonyl compound carbon monoxide releasers require high-energy, short-wavelength light (such as ultraviolet light) to induce carbon monoxide release, but such light has poor skin penetration and may be harmful to the body

Method used

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  • Photo-induced manganese carbonyl compound carbon monoxide releasing agent as well as preparation method and application thereof
  • Photo-induced manganese carbonyl compound carbon monoxide releasing agent as well as preparation method and application thereof
  • Photo-induced manganese carbonyl compound carbon monoxide releasing agent as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Compound 1 Preparation of:

[0036] The ligand 2-pyridinecarbaldehyde (32mg, 0.3mmol), p-chloroaniline (38mg, 0.3mmol) and Mn(CO)5Br (82mg, 0.3mmol) were placed in methanol (5mL) and heated to reflux, and the reaction The bottle was wrapped to avoid light, the mixed solution was refluxed for four hours, cooled, and finally filtered with suction to obtain the manganese carbonyl compound 1 based on the Schiff base ligand. 1H NMR (400MHz, DMSO) δ9.20 (d, J =4.8Hz,1H),8.89(d,J=6.7Hz,1H),8.24(d,J=4.4Hz,2H),7.78(s,1H),7.64(d,J=8.6Hz,2H), 7.58(t,J=7.3Hz,2H).

Embodiment 2

[0038] Compound 2 Preparation of:

[0039] Dissolve 2-pyridinecarbaldehyde (32mg, 0.3mmol), p-bromoaniline (51,6mg, 0.3mmol) and manganese pentacarbonyl bromide (82mg, 0.3mmol) in methanol (5ml) and heat to reflux, wrap the The reaction bottle was covered to avoid light, and the mixed solution was refluxed for four hours, cooled, and finally filtered with suction to obtain manganese carbonyl compound 2 (120 mg, yield 81%) based on Schiff base ligand. 1H NMR(400MHz,DMSO)δ9.21(s,1H),8.89(s,1H),8.25(s,2H),7.78(d,J=6.3Hz,3H),7.51(d,J=6.6Hz ,2H).

Embodiment 3

[0041] Compound 3 Preparation of:

[0042] Dissolve 2-pyridinecarbaldehyde (32mg, 0.3mmol), p-iodoaniline (65.7mg, 0.3mmol) and manganese pentacarbonyl bromide (82mg, 0.3mmol) in methanol (5ml) and heat to reflux. Cover it to avoid light, reflux the mixed solution for four hours, cool it, and finally filter it with suction to obtain manganese carbonyl compound 3 (124 mg, yield 71%) based on Schiff base ligand. 1H NMR(400MHz,DMSO)δ9.20(s,1H),8.87(s,1H),8.24(s,2H),7.93(d,J=5.9Hz,2H),7.78(s,1H),7.35 (d,J=5.4Hz,2H).

[0043] Application of compounds 1-3 releasing CO under the action of visible light

[0044] Test the relative properties of compounds 1-3 to release carbon monoxide under the irradiation of LED blue light, green light and red light IR(DMSO,υ / cm-1):

[0045] Such as Figure 1~3 As shown, compound 1 can decompose and release CO under the irradiation of LED blue light, green light or red light. Compound 1 has three obvious carbonyl infrared characteristic absorpt...

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Abstract

The invention discloses a light-induced manganese carbonyl compound carbon monoxide releasing agent and a preparation method and effect thereof; the light-induced manganese carbonyl compound carbon monoxide releasing agent has a structure as shown in the figure; the preparation method comprises the following steps: dissolving 2-pyridylaldehyde, halogen-containing aniline and Mn(CO)5Br in a solvent, and then carrying out heating reflux in a dark place, cooling and suction filtration to obtain the light-induced manganese carbonyl compound carbon monoxide releasing agent. The manganese carbonyl compound disclosed by the invention can be decomposed to release carbon monoxide under the action of visible light, and the defect that the manganese carbonyl compound generates carbon monoxide under the induction of ultraviolet light is overcome.

Description

technical field [0001] The invention relates to the technical fields of inorganic chemistry and pharmacy. More specifically, the present invention relates to a light-induced manganese carbonyl compound carbon monoxide release agent and its preparation method and application. Background technique [0002] Carbon monoxide (CO) is a toxic gas, but studies have found that it is a gas messenger molecule similar to NO. The human body produces a small amount of CO (ca. 10mL / day) every day, and participates in the regulation of many Physiological and pathological processes, such as vasodilation, anti-inflammation, anti-proliferation, anti-apoptosis, etc. Animal experiments have shown that CO has certain therapeutic effects on lung injury caused by oxygen overload or mechanical ventilation, sepsis, interstitial pulmonary fibrosis, and rejection after lung transplantation under certain conditions. Under different stress conditions, such as organ transplantation, ischemia-reperfusion...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F13/00C01B32/40
CPCC07F13/005C01B32/40Y02A50/20
Inventor 姜秀娟刘小明潘滢滢吴晓君李爱云王雪梅张俊蝶李菲
Owner JIAXING UNIV
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