Dual-functional radiation damage protection drug containing phenols and synthesis and application thereof

A radiation-damaged, dual-function technology, applied in the field of medicine, can solve problems such as damage to phenolic substances, and achieve the effect of low toxicity and obvious protective effect

Inactive Publication Date: 2015-08-19
XIAN TECHNOLOGICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It can quickly reduce ROS and scavenge harmful free radicals through proton transfer when radiation occurs, but this type of reaction is carried

Method used

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  • Dual-functional radiation damage protection drug containing phenols and synthesis and application thereof
  • Dual-functional radiation damage protection drug containing phenols and synthesis and application thereof
  • Dual-functional radiation damage protection drug containing phenols and synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Embodiment 1: the synthesis of above-mentioned compound (1):

[0055] 1.36 g (10.0 mmol) of p-hydroxyphenylacetaldehyde and 1.48 g (10.0 mmol) of dihydroxylamine were dissolved in 50 mL of methanol and refluxed for 24 h. A large amount of white insoluble matter was formed, filtered, and the filter cake was washed with a small amount of methanol. Suspend the filter cake in 50.0 mL CH 2 Cl 2 , cooled in an ice-water bath, and added 30.0 mL NaIO 4 (1.7 g) aqueous solution, the reaction was stopped after stirring for 15 min. After static separation, the aqueous phase was washed with CH 2 Cl 2 Extract twice, combine the organic phases, dry overnight, filter, remove the solvent under reduced pressure, and purify by column chromatography to obtain 1.15 g of the product with a yield of 44%. Mp: 145-147℃.R f =0.46 (CHCl 3 / CH 3 OH, 20:1). EI-MS(m / z) 263.1[M] + .IR(KBr) 3340 (OH); 1600, 1350, 1330, 910, 810, 670 cm -1 . Anal. Calcd for C 14 h 19 N 2 o 3 H, 7.28; ...

Embodiment 2

[0056] Embodiment 2: the synthesis of above-mentioned compound (2):

[0057] Dissolve 1.66 g (10.0 mmol) of p-2-methoxy-4-A; hydroxybenzaldehyde and 1.48 g (10.0 mmol) of dihydroxylamine in 50 mL of methanol, and reflux for 24 h. A large amount of white insoluble matter was formed, filtered, and the filter cake was washed with a small amount of methanol. Suspend the filter cake in 50.0 mL CH 2 Cl 2 , cooled in an ice-water bath, and added 30.0 mL NaIO4 (1.7 g) aqueous solution, the reaction was stopped after stirring for 15 min. After static separation, the aqueous phase was washed with CH 2 Cl 2 Extracted twice, combined the organic phases, dried overnight, filtered, removed the solvent under reduced pressure, and purified by column chromatography to obtain 1.65 g of the product, with a yield of 56%. Mp: 133-135℃.R f = 0.60(CHCl 3 / CH 3 OH, 20:1). EIMS(m / z) 294.3 [M] + .IR (KBr) 1610, 1430, 1322, 996, 820, 790 cm -1 . Anal. Calcd for C 15 h 21 N 2 o 4 : C, 62....

Embodiment 3

[0058] Embodiment 3: the synthesis of above-mentioned compound (6):

[0059] 1.50 g (10.0 mmol) of 4-hydroxyphenylpropionaldehyde and 1.48 g (10.0 mmol) of dihydroxylamine were dissolved in 50 mL of methanol and refluxed for 24 h. A large amount of white insoluble matter was formed, filtered, and the filter cake was washed with a small amount of methanol. Suspend the filter cake in 50.0 mL CH 2 Cl 2 , cooled in an ice-water bath, and added 30.0 mL NaIO 4 (1.7 g) aqueous solution, the reaction was stopped after stirring for 15 min. After static separation, the aqueous phase was washed with CH 2 Cl 2 Extracted twice, combined the organic phases, dried overnight, filtered, removed the solvent under reduced pressure, and purified by column chromatography to obtain 1.13 g of the product, with a yield of 41%. Mp: 122-124℃.R f =0.62 (CHCl 3 / CH 3 OH, 20:1). EI-MS (m / z) 278[M] + .IR (KBr) 1599, 1440, 1350, 1020, 800 cm -1 . Anal. Calcd for C 15 h 21 N 2 o 3 : C, 64.96;...

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PUM

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Abstract

The invention relates to a dual-functional radiation damage protection drug containing phenols and synthesis and application thereof. Phenolic compound acting as radiation protection drug is carried out in a stoichiometric ration of 1:1, so there is nothing to do about damage arising from high-dose and continuous radiation. The related compound in the invention has a structure as described in the description, wherein at least one of R1-R5 is OH, while others are respectively selected from H, OCH3, NO2, and X, and n is 1 or 2. The drug has outstanding protection effect on damages caused by ionizing radiation and non-ionizing radiation, has a similar control effect with anti-radiation drug WR2721 in current market, however, the drug has lower toxicity, and can be used in the protection against damage caused by high-dose and continuous radiation.

Description

technical field [0001] The invention relates to a medicine, in particular to a phenolic bifunctional radiation damage protection medicine and its synthesis and application. Background technique [0002] Electromagnetic radiation widely exists in many fields, becoming an "invisible pollution source" and seriously threatening human health. Radiation can cause a series of physiological and pathological changes in the body, causing serious radiation damage. The target molecules of radiation are genomic DNA and cell membrane. Among them, DNA is prone to structural changes when ionized, which is the root of cell mutation and cancer. Radiation mutagenesis, radiation carcinogenesis, organ lesions, etc. Therefore, the research on the protection of radiation damage has always been a topic of great concern to scholars from all over the world. [0003] There are many types of radiopharmaceutical protective agents currently being studied, among which phenolic compounds are a class of ...

Claims

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Application Information

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IPC IPC(8): C07D233/22A61K31/4174A61P39/00
CPCC07D233/22
Inventor 田敏张改牛小玲孙晓莉
Owner XIAN TECHNOLOGICAL UNIV
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