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Nitrogen-oxygen free radical compound with anti-hypoxia injury activity and preparation and application thereof

A nitroxide free radical, anti-hypoxia technology, applied in organic chemistry, anti-toxic agent, drug combination, etc., can solve the problems of increased generation of free radicals, decompensation of antioxidant system, etc.

Inactive Publication Date: 2015-03-11
贾正平
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Studies have shown that hypoxia can lead to oxidative stress in the body, activation of the mitochondrial redox pathway, decompensation of the antioxidant system, and increased production of free radicals, leading to the occurrence of hypoxia-related diseases

Method used

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  • Nitrogen-oxygen free radical compound with anti-hypoxia injury activity and preparation and application thereof
  • Nitrogen-oxygen free radical compound with anti-hypoxia injury activity and preparation and application thereof
  • Nitrogen-oxygen free radical compound with anti-hypoxia injury activity and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1, the synthesis and structural characterization of compound 1

[0054] (1) Synthesis of 4-(2-bromoethoxy)benzaldehyde: 1.22 g (10 mmol) 4-hydroxybenzaldehyde, 2.07 g (15 mmol) K 2 CO 3 and 2.82 g (15 mmol) of 1,2-dibromoethane were dissolved in 50 mL of acetone, refluxed for 8 h, and the reaction was stopped. After cooling to room temperature, the acetone was removed under reduced pressure, and 100 mL of water was added. 2 Cl 2 Extraction (50 mL × 3), combined organic phase, anhydrous Na 2 SO 4 Dry overnight, filter, remove the solvent under reduced pressure and separate by flash column chromatography to obtain 4-(2-bromoethoxy)benzaldehyde. White solid 1.83 g, yield 80%. 1 H-NMR (CDCl 3 , 400 MHz) δ : 9.89(s, 1H), 7.85(d, J =8.8 Hz, 2H), 7.02 (d, J =8.4 Hz, 2H), 4.38 (t, J =6.0 Hz, 2H), 3.68 (t, J = 6.0 Hz, 2H). ESI-MS (m / z): 230 [M+H] + .

[0055] (2) Synthesis of 4-(2-(dimethylamino)ethoxy)benzaldehyde: 2.29 g (10 mmol) 4-(2-bromoethoxy)benz...

Embodiment 2

[0058] Embodiment 2, the synthesis and structural characterization of compound 2

[0059] (1) Synthesis of 4-(2-bromoethoxy)benzaldehyde: same as Example 1.

[0060] (2) Synthesis of 4-(2-(diethylamino)ethoxy)benzaldehyde: 2.29 g (10 mmol) 4-(2-bromoethoxy)benzaldehyde, 2.07 g (15 mmol) K 2 CO 3 and 15 mmol of diethylamine were dissolved in 50 mL of acetonitrile, and refluxed for 11 h. After the reaction was complete as monitored by TLC, the reaction system was cooled to room temperature, filtered, and the filter cake was washed with a small amount of acetonitrile. After removing the acetonitrile under reduced pressure, flash column chromatography Separation gave 4-(2-(diethylamino)ethoxy)benzaldehyde. 1.50 g of light yellow oily matter, yield 68%. 1 H-NMR (CDCl 3 , 400 MHz) δ : 9.88(s, 1H), 7.83(d, J =8.8 Hz, 2H), 7.01 (d, J =8.4 Hz, 2H), 4.13(t, J =6.0 Hz, 2H), 2.90 (t, J=6.0 Hz, 2H) 2.68~2.62 (m, 4H), 1.08 (t, J =6.8Hz, 6H). 13 C-NMR (CDCl 3 , 100 MHz) δ : 190...

Embodiment 3

[0063] Example 3: Synthesis and structural characterization of compound 3

[0064] (1) Synthesis of 4-(2-bromoethoxy)benzaldehyde: same as Example 1.

[0065] (2) Synthesis of 4-(2-(tetrahydropyrrolyl)ethoxy)benzaldehyde: 2.29 g (10 mmol) 4-(2-bromoethoxy)benzaldehyde, 2.07 g (15 mmol) K 2 CO 3 and 15 mmol tetrahydropyrrole were dissolved in 50 mL acetonitrile, and refluxed for 17 h. After the reaction was complete as monitored by TLC, the reaction system was cooled to room temperature, filtered, and the filter cake was washed with a small amount of acetonitrile. After removing the acetonitrile under reduced pressure, flash column chromatography After separation, 1.35 g of light yellow oil was obtained, with a yield of 62%. 1 H-NMR (CDCl 3 , 400 MHz) δ : 9.88(s, 1H), 7.83(d, J =8.4 Hz, 2H), 7.02 (d, J =8.8 Hz, 2H), 4.21(t, J =5.6 Hz, 2H), 2.95 (t, J =6.0 Hz, 2H), 2.65 (s, 4H), 1.86 (s, 4H). 13 C-NMR (CDCl 3 , 100 MHz) δ : 190.7, 163.7, 131.9, 129.9, 114.8, 67.3, 54....

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Abstract

The invention discloses a nitrogen-oxygen free radical compound with anti-hypoxia injury activity. The structural general formula of the nitrogen-oxygen free radical compound is shown as the following formula. Animal activity tests show that the nitrogen-oxygen free radical compound can enable the contents of H2O2, NO, MDA and LD in the brain tissue of an anoxic mouse to tend to be normal, enable the SOD, GSH-px and LDH activities to be significantly improved, enable the CAT activity to tend to be normal, and enable the anoxic mouse to have a remarkable anti-hypoxia activity; the nitrogen-oxygen free radical compound has a remarkable prevention and treatment effect on acute high altitude diseases, cerebral ischemia and hypoxia diseases and myocardial ischemia hypoxia diseases caused by hypobaric hypoxia on plateau.

Description

technical field [0001] The field of chemical synthesis and medical application of the present invention relates to a nitrogen-oxygen free radical compound, in particular to a class of nitrogen-oxygen free radical compound with anti-hypoxic damage activity; the present invention also relates to a synthesis method of the compound and its Preparation of anti-hypoxic drugs from injury applications. Background technique [0002] With the continuous acceleration of people's life rhythm, hypoxia has become a quite common pathological phenomenon. Various factors, such as the reduction of oxygen content or partial pressure in the atmosphere in the environment, respiratory, blood, circulatory and other system diseases, and the body's oxygen consumption is greater than the supply can all lead to hypoxic symptoms in the body. Especially the special low-pressure and low-oxygen environment in plateau areas often causes acute altitude sickness such as headache, heart palpitations, chest t...

Claims

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Application Information

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IPC IPC(8): C07D233/22C07D401/12C07D403/12C07D233/60A61P39/00A61P9/10
CPCC07D233/22C07D233/60C07D401/12C07D403/12
Inventor 景临林马慧萍樊鹏程何蕾蒙萍贾正平
Owner 贾正平
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