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Light induced carbon monoxide release molecule and preparation method thereof

A carbon monoxide and light-induced technology is applied to zinc organic compounds, 2/12 group organic compounds without C-metal bonds, anti-toxic agents, etc. It can solve the problems of short irradiation wavelength, unfavorable application, and restricted development, etc., and achieve process can be achieved control, good CO release performance, and reduced side effects

Inactive Publication Date: 2017-11-03
NORTHWEST UNIV(CN)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the design strategy of photoinduced carbon monoxide releasing molecules (photoCORMs) is still mainly in the early state of metal carbonyl compounds, and most of the researches focus on transition metal carbonyl compounds coordinated by natural amino acids, transition metal carbonyl compounds coordinated by pyridine ligands, There are other ligand-coordinated transition metal carbonyl compounds. Most of these complexes have good water solubility, but the irradiation wavelength for inducing CO release is relatively short, and some reactions are reversible and inherently unstable, which seriously restricts the development of this field. Not conducive to application in vivo

Method used

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  • Light induced carbon monoxide release molecule and preparation method thereof
  • Light induced carbon monoxide release molecule and preparation method thereof
  • Light induced carbon monoxide release molecule and preparation method thereof

Examples

Experimental program
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Embodiment 1

[0041] Step 1. Preparation of CO release unit

[0042] 4-methoxyflavonol (4-MeOFLH) was synthesized from p-methoxybenzaldehyde and 2-hydroxyacetophenone as starting materials, and the product was used as CO releasing unit.

[0043] refer to figure 2 , the method for synthesizing 4-methoxy flavonol is as follows:

[0044] in N 2 Under protection, p-methoxybenzaldehyde (0.12 mL, 1 mmol) was dissolved in 10 mL of ethanol, and 1 mL of 25% NaOH aqueous solution was added to obtain a colorless mixed solution. A solution of 2-hydroxyacetophenone (0.12 mL, 1 mmol) in ethanol (3 mL) was added to the above colorless mixed solution, and the reaction was continued for 5 h. Cool the reactant in an ice bath, add dropwise 30% acetic acid solution to adjust the pH to weak acidity, continue stirring for 30 min, filter, collect the precipitate, and dry to give chalcone dark yellow powder (0.16g, 61.3%, Mp: 91°C) . The obtained chalcone (0.16 g, 0.62 mmol) was dissolved in 5 mL of absolute...

Embodiment 2

[0073] Step 1. Preparation of CO release unit

[0074] 4-Methoxyflavanol (4-MeOFLTH) was synthesized from p-methoxybenzaldehyde and 2-hydroxyacetophenone as starting materials, and the product was used as CO releasing unit.

[0075] The synthesis process is divided into two steps:

[0076] (1) Using p-methoxybenzaldehyde and 2-hydroxyacetophenone as starting materials to first synthesize 4-methoxyflavonol, this step is exactly the same as step 1 in Example 1, and will not be repeated;

[0077] (2) The 4-methoxyflavonol synthesized in the previous step is used as a reactant to synthesize 4-methoxyflavonol, and the synthesis process will be described in detail below.

[0078] refer to image 3 , the method for synthesizing 4-methoxyl thioketol is as follows:

[0079] in N 2 Under protection, dissolve 4-methoxyflavonol (1.01g, 3.78mmol) in 120mL toluene, stir at room temperature for 5min, add Lawson's reagent (1.2mg, 3.03mmol), reflux for 30min, the solution turns dark red, c...

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Abstract

The invention discloses light induced carbon monoxide release molecules (photoCORMs) and a preparation method thereof. The photoCORMs is of modular design and is synthesized from a CO release unit, support ligand and metal zinc ions, wherein 4-MeOFLH or 4-MeOFLTH is adopted as a CO release unit; 6-Me2TPA is used as the support ligand; the CO release unit and the support ligand independently exist in photoCORMs. The preparation method of the photoCORMs comprises the following steps: (1) by taking methoxybenzaldehyde and 2-phenol acetophenone as initial raw materials, synthesizing 4-MeOFLH or 4-MeOFLTH; (2) by taking 2-(aminomethyl) pyridine as another initial raw material, synthesizing 6-Me2TPA; (3) enabling the CO release unit and the support ligand to react with metal zinc ions, thereby synthesizing photoCORMs. The light induced carbon monoxide release molecules have the beneficial effects that firstly photoCORMs is good in CO release property, and as a CO release medicine, is capable of greatly reducing side effects on bodies, and CO release can be induced through visible light; secondly, the molecule is definite in synthesis step, controllable in process and possible in batched production.

Description

technical field [0001] The invention relates to chemical substances and a preparation method thereof, in particular to light-induced carbon monoxide releasing molecules (photoCORMs) and a preparation method thereof, belonging to the technical field of chemistry, and in particular to the technical field of carbon monoxide treatment reagents. Background technique [0002] Carbon monoxide (CO) is a well-known invisible killer, but it is now recognized by scientists as a very important molecule in biological systems. In the human body, CO is mainly produced by the degradation of heme catalyzed by heme oxygenase (HO-1 or HO-2). Several recent simulation studies in animals (including: cardiovascular disease, inflammatory disease and organ transplantation) have found that the production of a small amount of CO is beneficial to the recovery of the disease, mainly showing that CO can help anti-inflammation, anti-apoptosis, and Can promote vasodilation and protect tissues from tissue...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F3/06A61P29/00A61P9/08A61P39/00
CPCC07F3/003
Inventor 张荣兰杨维兴苏媛媛赵建社
Owner NORTHWEST UNIV(CN)
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