A kind of hydroxypyridone ligand and its application

A hydroxypyridone and ligand technology, applied in the directions of organic chemistry, antidote, drug combination, etc., can solve the problems of high synthesis cost, difficult to remove nuclide, large side effects, etc., and achieves safe synthesis route, easy complexation, cost low effect

Active Publication Date: 2020-07-24
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But DTPA-CaNa 3 There are many limitations and deficiencies: First, DTPA-CaNa 3 It only has good expulsion-promoting effect on plutonium and americium, and almost no effect on nuclide with high contact probability such as uranium and thorium, and DTPA-CaNa 3 It cannot enter the cell through the cell membrane. Once the nuclide is deposited and bound to the protein in the cell, DTPA-CaNa 3 It cannot be discharged; secondly, as a nuclear emergency drug, DTPA-CaNa 3 Only the effect of injection to promote excretion is better, almost no oral effect, which brings inconvenience to nuclear accident emergency; in addition, DTPA-CaNa 3 It is difficult to remove nuclides deposited in bone, and to remove the largest amount of nuclides in the body, multiple injections of DTPA-CaNa are required 3 , side effects
However, high-temperature and high-pressure reactions are involved in the synthesis process, and the synthesis cost is high; and 3,4,3-LI(1,2-HOPO) is difficult to synthesize, has low yield and high toxicity, and cannot be used in large quantities; while 5-LIO(Me -3,2-HOPO) has a good broad-spectrum stimulating effect, but the oral effect is poor

Method used

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  • A kind of hydroxypyridone ligand and its application
  • A kind of hydroxypyridone ligand and its application
  • A kind of hydroxypyridone ligand and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1 Synthesis of 1,3-bis[(3-hydroxy-2-pyridone)-1-ethyl]acetamido-propanediamine (3,2-HOPO-3C) The synthetic route of this example is as follows :

[0050]

[0051] Specifically include the following steps:

[0052] Weigh 11.1 g of 2,3-dihydroxypyridine ((1), 0.1 mol) in the reaction flask, add 83.5 g of ethyl bromoacetate (0.5 mol), and mix N 2 Pass to the reaction liquid below the surface and stir for 1h, then under N 2Protection, reflux reaction at 150°C for 24h. After the reaction, the reaction bottle was removed from the oil bath, cooled to room temperature, and a solid was precipitated, then the reaction solution was filtered, the solid was washed with acetone for 3-5 times, and then recrystallized with ethanol. After drying in a vacuum oven for 24 hours, the off-white product (2) was obtained, with a yield of 13.7 g and a yield of 70%. Its NMR and mass spectrometry test results are as follows:

[0053] 1 H NMR (400MHz, DMSO) δ7.43-7.36(m,2H),7.34-7...

Embodiment 2

[0059] Example 2 Synthesis of 2,2'-oxybis[(3-hydroxyl-2-pyridone)-1-ethyl]acetamido-ethylamine (3,2-HOPO-2NO)

[0060] The synthetic route of the present embodiment is as follows:

[0061]

[0062] Specifically include the following steps:

[0063] Weigh 11.1 g of 2,3-hydroxypyridine ((1), 0.1 mol) in the reaction flask, add 83.5 g of ethyl bromoacetate (0.5 mol), and mix N 2 Pass to the reaction liquid below the surface and stir for 1h, then under N 2 Protection, reflux reaction at 150°C for 24h. After the reaction, the reaction bottle was removed from the oil bath, cooled to room temperature, and a solid was precipitated, then the reaction solution was filtered, the solid was washed with acetone for 3-5 times, and then recrystallized with ethanol. After drying in a vacuum oven for 24 hours, the off-white product (2) was obtained, with a yield of 13.7 g and a yield of 70%.

[0064] Get the above-mentioned product (2) 10g (0.05mol) and dissolve in 300ml of 90% methanol ...

Embodiment 3

[0069] Example 3 Synthesis of 3,3'-oxybis[(3-hydroxyl-2-pyridone)-1-ethyl]acetamido-propylamine (3,2-HOPO-3NO)

[0070] The synthetic route of the present embodiment is as follows:

[0071]

[0072] Specifically include the following steps:

[0073] Weigh 11.1 g of 2,3-hydroxypyridine ((1), 0.1 mol) in the reaction flask, add 83.5 g of ethyl bromoacetate (0.5 mol), and mix N 2 Pass to the reaction liquid below the surface and stir for 1h, then under N 2 Protection, reflux reaction at 150°C for 24h. After the reaction, the reaction bottle was removed from the oil bath, cooled to room temperature, and a solid was precipitated, then the reaction solution was filtered, the solid was washed with acetone for 3-5 times, and then recrystallized with ethanol. After drying in a vacuum oven for 24 hours, the off-white product (2) was obtained, with a yield of 13.7 g and a yield of 70%.

[0074] Get the above-mentioned product (2) 10g (0.05mol) and dissolve in 300ml of 90% methanol...

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Abstract

The invention relates to a hydroxy-pyridone ligand; a structural formula of the hydroxy-pyridone ligand is one of two formulas described in the description, wherein a structural formula of R is described in the description, R1 is hydrogen, alkyl of C2-C4, halogen, hydroxyl or carboxyl, m, n and p are independently selected from 1, 2 or 3, and r is 1 or 2. A preparation method of the hydroxy-pyridone ligand comprises the following steps: dissolving a compound as shown in a formula (1) into an organic solvent, and then enabling the obtained solution to react with an amino-terminated compound at the temperature of 25-35 DEG C in presence of a catalyst to obtain an intermediate compound; enabling the obtained intermediate compound to have a palladium-carbon reduction reaction in an organic solvent to obtain the hydroxy-pyridone ligand, wherein a structural formula of the compound as shown in the formula (1) is described in the description, and R1 is hydrogen, alkyl of C2-C4, halogen, hydroxyl, carboxyl or aryl. The invention also provides application of the hydroxy-pyridone ligand as chelating agents for lanthanide elements, actinide elements and / or heavy metal elements. The invention further provides application of the hydroxy-pyridone ligand as a chelating agent for the element in nuclear waste, wherein the element in the nuclear waste is Sr, Cs, Tc or I.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a hydroxypyridone ligand and its application. Background technique [0002] With the development of nuclear power industry, people attach great importance to nuclear safety. The March 11, 2011 Fukushima nuclear power plant nuclear accident in Japan is considered the worst nuclear disaster since the 1986 Cherkepely nuclear accident in Ukraine. The explosion of the Fukushima nuclear power plant led to nuclear leakage. These radioactive nuclides diffuse and transfer in the environment through various channels. Some long-lived and highly radioactive nuclides, such as thorium, uranium and plutonium and other actinides, may pass through the skin, breathing and Food and other channels enter the human body. Such nuclides, especially high-radioactive nuclides such as plutonium and americium, are not only highly radioactive, but also highly chemically toxic. After entering the body, they...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/69A61P39/02
CPCC07D213/69
Inventor 王殳凹第五娟王晓梅
Owner SUZHOU UNIV
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