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Radiation protection compound as well as synthesis method and application thereof

A technology for radiation protection and synthesis method, applied in the field of medicine, can solve problems such as mitochondrial dysfunction, and achieve the effects of high yield, mild reaction conditions and good biocompatibility

Inactive Publication Date: 2020-04-17
FOURTH MILITARY MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Studies have shown that a large number of different types of free radicals keep the mitochondria in a state of continuous oxidative stress, producing a large number of reactive oxygen species ROS (Reactive Oxygens), and then causing mitochondrial dysfunction

Method used

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  • Radiation protection compound as well as synthesis method and application thereof
  • Radiation protection compound as well as synthesis method and application thereof
  • Radiation protection compound as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The present embodiment has the radioprotective compound of general structural formula (I),

[0040]

[0041] Among them, R 1 ~R 4 , R' 1 ~R' 4 = NO 2 , OH, F, Cl, Br, H;

[0042] The prolinol of general structural formula (I) is L-prolinol.

[0043] The specific process of the synthetic method of radiation protection compound of the present invention is:

[0044] Step 1, the synthesis of intermediate 1

[0045] Weigh 2.62g of triphenylphosphine (TPP, 10mmol) and 2.07g of 6-bromohexanoic acid (10.5mmol), dissolve them in anhydrous acetonitrile, then reflux for 16h under nitrogen protection and stirring, and use TLC to determine whether the reflux At the end of the reaction, the reaction solution obtained by the reflux reaction was placed in a rotary evaporator to spin dry the solvent, and the obtained solid was ground into a powder with a mortar, washed 2 to 3 times with n-hexane and then suction filtered to obtain 2.94 g of a white solid. Intermediate 1, afte...

Embodiment 2

[0055] The difference between this embodiment and Example 1 is that the prolinol in the general structural formula (I) of the radioprotective compound is L-prolinol;

[0056] In the synthesis process of the radiation protection compound, the L-prolinol added in step 2 is replaced by D-prolinol, and the corresponding intermediate 2, intermediate 3 and intermediate 4 obtained are all in D-configuration, and in step 5 The product obtained was TPP-D-NIT-1.

Embodiment 3

[0058] The present embodiment has the radioprotective compound of general structural formula (II),

[0059]

[0060] The prolinol of general structural formula (II) is L-prolinol.

[0061] The specific process of the synthetic method of radiation protection compound of the present invention is:

[0062] Step 1, the synthesis of intermediate 5

[0063] Dissolve 2.62g of triphenylphosphine (TPP, 10mmol) and 7.3g of 1,6-dibromohexane (30mmol) in anhydrous acetonitrile and stir, then reflux for 12h, and use TLC to detect the end point of the reaction; The product system obtained by the reaction was placed in a rotary evaporator to spin dry the solvent, separated by column chromatography to obtain 3.42g light yellow oil, and then purified by column chromatography (eluent was made of dichloromethane and methanol according to the volume of 10:1 ratio prepared) to obtain intermediate 5, after calculation, the yield of intermediate 5 is 80%; the mass spectrometry analysis result H...

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Abstract

The invention discloses a radiation protection compound with a structural general formula (I) or (II). The synthesis method comprises the steps: enabling triphenylphosphine to react with 6-bromohexanoic acid or 1,6-dibromohexane to obtain a triphenylphosphine cationic compound, sequentially performing acylation, etherification, reduction and oxidation on L-prolinol or D-prolinol, and combining with the triphenylphosphine cationic compound to obtain TPP-L / D-NIT-1 or TPP-L / D-NIT-2; the radiation protection compound is applied to the anti-radiation damage pharmaceutical composition. The radiationprotection compound is a mitochondria targeting nitroxide free radical compound with chirality and has an obvious radiation protection effect at an animal level, and a chiral prolinol structural unitin the radiation protection compound is similar to a proline structure in a biological organism, so that the biocompatibility is better; the synthesis method disclosed by the invention is mild in condition and good in reproducibility; the radiation protection compound provided by the invention has relatively high practical value.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a radiation protection compound and its synthesis method and application. Background technique [0002] In recent years, nuclear technology has entered a period of rapid development, and nuclear technology has been more and more widely used in the fields of national defense, industry, agriculture, and medical treatment in various countries. But while nuclear energy benefits mankind, it also poses severe challenges to human safety and health. So far, although researchers at home and abroad have reported the experimental results of multiple anti-radiation damage drugs, so far, only amifostine (WR2721) is the only anti-radiation drug approved by the US FDA, and its curative effect depends on The required dose is close to the toxic dose, which greatly limits its popularization. There is still an urgent need for radiation protection drugs with definite and ideal curativ...

Claims

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Application Information

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IPC IPC(8): C07F9/6558A61P39/00A61K31/675
CPCC07F9/65583A61P39/00
Inventor 王海波王晋谭光国黄雁茹石红伟
Owner FOURTH MILITARY MEDICAL UNIVERSITY
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