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A kind of water-soluble pegylated fischer carbene compound and preparation method thereof

A technology for PEGylation and compounding, which is applied in the field of water-soluble PEGylation Fischer carbene compounds and their preparation, can solve problems such as difficult derivatization of ligands, achieve simple synthesis methods, reduce toxicity, and increase water solubility

Inactive Publication Date: 2018-03-06
SHAANXI NORMAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The Ford team used tungsten carbonyl as the precursor to release molecules, and used traditional water-soluble phosphorus ligands to greatly increase the water solubility of tungsten carbonyl. CO release experiments showed that if it is placed in a dark environment, it will be stable in the air for a period of time. Excited by light in the range of 300-370nm, this type of compound can be photodecomposed to release CO, but this ligand is not easy to derivatize, and only one release molecule can be synthesized (Inorg.Chem, 2010, Vol. 49, pp. 1180-1185)

Method used

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  • A kind of water-soluble pegylated fischer carbene compound and preparation method thereof
  • A kind of water-soluble pegylated fischer carbene compound and preparation method thereof
  • A kind of water-soluble pegylated fischer carbene compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Take the preparation of the following PEGylated Fischer carbene compound as an example:

[0027]

[0028] Take by weighing 500.2mg (1mmol) Fischer carbene of chromium pentacarbonyl shown in formula 1-1 and 265.6mg (1mmol) monoethylene glycol monomethyl ether amino acid ester hydrochloride and place in Schlenk bottle, adopt vacuum line operation technique, In the absence of water and oxygen, N 2 (99.999%) protection, add 15mL of dry methanol and 140 μL (1mmol) triethylamine, stir at room temperature for 5 hours, column chromatography (with the volume ratio of dichloromethane and petroleum ether being 3:1 mixed solution as the elution liquid), to obtain oily yellow PEGylated Fischer carbene compound (112.9mg, yield 64%), its reaction equation is as follows:

[0029]

[0030] The structural characterization data of the resulting product is: IR(CH 2 Cl 2 , cm -1 ): Vco=2056cm -1 , 1928cm -1 , 1748cm -1 ; 1 H NMR (400MHz, CDCl 3 )δ(ppm): 9.34(s, 1H), 9.16-9.04...

Embodiment 2

[0032] Take the preparation of the following PEGylated Fischer carbene compound as an example:

[0033]

[0034] In Example 1, the monoethylene glycol monomethyl ether glycinate hydrochloride used is replaced with equimolar monoethylene glycol monomethyl ether phenylalanine hydrochloride, and other steps are the same as in Example 1 to obtain Yellow oily PEGylated Fischer carbene compound (276mg, yield 62%), its reaction equation is as follows:

[0035]

[0036] The structural characterization data of the resulting product is: IR(CH 2 Cl 2 , cm -1 ): Vco=2056cm -1 , 1927cm -1 , 1744cm -1 ; 1 H NMR (400MHz, CDCl 3 )δ (ppm): 9.16 (s, 1H), 8.75 (s, 0.35H), 7.33 (s, 3H), 7.19 (s, 2H), 4.77 (s, 1H), 4.46-4.28 (m, 2H) , 3.58(d, 2H), 3.40(s, 3H), 3.17(d, 2H), 2.29(s, 3H); 13 C NMR (101MHz, CDCl 3 )δ (ppm): 282.38, 224.13, 218.82, 170.46, 135.12, 130.83, 129.44, 71.27, 66.72, 61.62, 60.32, 40.60, 36.95.

[0037] The obtained product was dissolved in dichloromethane, a...

Embodiment 3

[0039] Take the preparation of the following PEGylated Fischer carbene compound as an example:

[0040]

[0041] In Example 1, the monoethylene glycol monomethyl ether glycinate hydrochloride used is replaced with equimolar monoethylene glycol monomethyl ether tyrosine hydrochloride, and other steps are the same as in Example 1 to obtain yellow Oily PEGylated Fischer carbene compound (103mg, yield 23%), its reaction equation is as follows:

[0042]

[0043] The structural characterization data of the resulting product is: IR(CH 2 Cl 2 , cm -1 ): Vco=2056cm -1 , 1928cm -1 , 1735cm -1 ; 1 H NMR (400MHz, CDCl 3 )δ (ppm): 9.14 (s, 1H), 7.02 (s, 2H), 6.82 (s, 2H), 6.51-5.74 (m, 2H), 4.70 (s, 1H), 4.09 (s, 2H), 3.86(s, 3H), 3.08(d, 2H), 2.32(s, 3H); 13 C NMR (101MHz, CDCl 3 )δ (ppm): 285.04, 222.78, 217.44, 171.61, 155.82, 130.66, 125.76, 116.00, 69.87, 65.15, 60.49, 58.90, 38.23, 35.57.

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Abstract

The invention discloses a water-soluble pegylation Fischer carbene complex. The structural formula of the complex can be seen in the description, wherein M represents Cr or Mo, R represents any one of H- and other three groups (please see the groups in the description), and n is an integer from 1 to 3. The complex is prepared from Fischer carbine and methoxypolyethylene glycol amino-acid ester hydrochloride under the catalysis of triethylamine at the room temperature, and the synthesis method is simple. Fischer carbine is modified by polyethylene glycol, and therefore the thermal stability and biological compatibility of Fischer carbine are improved, the toxicity of molecules is reduced, the water solubility of molecules is greatly improved, the combined complex can slowly release CO in a water phase, can rapidly release CO molecules under the irradiation of ultraviolet light and has good responsiveness to light, and a new road is developed for water-soluble CO molecule release.

Description

technical field [0001] The invention belongs to the technical field of synthetic medicine, in particular to a water-soluble pegylated Fischer carbene compound and a preparation method thereof. Background technique [0002] CO has always been called the "silent killer", but with the small messenger molecules NO and H 2 With the development of S, people gradually realize that CO is also an important messenger molecule in the human body, which has many therapeutic effects such as relaxing cardiovascular, inhibiting malignant cell proliferation, protecting ischemia-reperfusion injury, anti-inflammation, and antibacterial; but CO has many therapeutic effects in Small solubility in water, easy to combine with hemoglobin in the body, difficult to quantitatively transport and other limitations. Although transition metal carbonyl compound-like carbon monoxide releasing molecules (CO Releasing Molecules, CO-RMs) have solved the limitation of transport, due to the strong hydrophobicit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F11/00
CPCC07F11/00
Inventor 张伟强孙红霞周玲玲杨淑红杨积娟陈冬婷张霞丽张雷
Owner SHAANXI NORMAL UNIV
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