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Mitochondrial function protecting agent, preparation method therefor and application thereof

A route and reaction technology, applied in the field of medicine, can solve problems such as insufficient efficacy, limited resistance to oxidative damage in neurodegenerative diseases, poor selectivity of antioxidants, etc., to achieve clear protective effects, protect neuron cells, and efficiently remove harmful free radicals Effect

Inactive Publication Date: 2015-10-28
FOURTH MILITARY MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are many kinds of antioxidants, such as vitamin E (tocopherol), coenzyme Q, curcumin, etc., due to the poor selectivity of these traditional antioxidants, they cannot selectively enter the ROS-bursting mitochondria, which is very important for the resistance to neurodegeneration. Oxidative damage caused by disease is limited
This suggests that mitochondria-targeted antioxidants will overcome the shortcomings of traditional antioxidants that are less effective

Method used

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  • Mitochondrial function protecting agent, preparation method therefor and application thereof
  • Mitochondrial function protecting agent, preparation method therefor and application thereof
  • Mitochondrial function protecting agent, preparation method therefor and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: the synthetic method of compound 1

[0024] In 4.41 g (30 mmol) 1H-indole-2-carbaldehyde and added to 100 mL CH 2 Cl 2 Add 4.4 mL of triethylamine, stir magnetically under ice bath, then slowly add 30 mL of CH containing 2.01 g (30 mmol) bromoacetyl bromide dropwise to the reaction solution 2 Cl 2 solution. After the dropwise addition, the ice bath was removed, and the reaction was stirred at room temperature for 24 h, the organic phase was separated, washed twice with water, and the organic phase was washed with anhydrous MgSO 4 After drying, the solvent was removed to obtain a white solid product, which was purified by column chromatography to obtain 7.16 g of the product, with a yield of 89%. MS( m / z ): 266.01[M] + ; 1 H NMR (CDCl 3 ): d 9.25(s, 1H), 7.23(d, 1H), 7.20(d, 1H), 7.14(s, 1H), 7.04(s, 1H), 4.90(m, 1H), 4.25(s, 1H ), 3.11(d, 2H); Anal. Calcd for C 11 h 10 BrNO 2 : C,49.28; H, 3.76; N,5.22, Found: C,49.21; H, 3.79; N,5.28%.

[0...

Embodiment 2

[0027] Embodiment 2: the synthetic method of compound 2

[0028] In 6.21 g (30 mmol) of 5-methoxy-6-methoxy-1H-indole-2-carbaldehyde and added to 100 mL of CH 2 Cl 2 Add 4.4 mL of triethylamine, stir magnetically under ice bath, then slowly add 30 mL of CH containing 2.01 g (30 mmol) bromopropionyl bromide dropwise to the reaction solution 2 Cl 2 solution. After the dropwise addition, the ice bath was removed, and the reaction was stirred at room temperature for 24 h, the organic phase was separated, washed twice with water, and the organic phase was washed with anhydrous MgSO 4After drying, the solvent was removed to obtain a white solid product, which was purified by column chromatography to obtain 7.98 g of the product, with a yield of 78%. MS( m / z ): 341.62 [M] + ; 1 H NMR (CDCl 3 ): d 9.59 (d, 1H), 6.84(s, 1H), 6.73(s, 1H), 4.87(m, 1H), 3.81(s, 6H), 3.71(m, 2H), 3.15(m, 2H ), 2.74(m, 2H); Anal. Calcd for C 14 h 16 BrNO 2 : C,49.14; H, 4.71; N,4.09, Found: C...

Embodiment 3

[0031] Embodiment 3: the synthetic method of compound 5

[0032] In 5.76 g (30 mmol) of 7-nitro-1H-indole-2-carbaldehyde and added to 100 mL CH 2 Cl 2 Add 4.4 mL of triethylamine, stir magnetically under ice bath, then slowly add 30 mL of CH containing 2.01 g (30 mmol) bromoundecanoyl bromide to the reaction liquid 2 Cl 2 solution. After the dropwise addition, the ice bath was removed, and the reaction was stirred at room temperature for 24 h, the organic phase was separated, washed twice with water, and the organic phase was washed with anhydrous MgSO 4 After drying, the solvent was removed to obtain a white solid product, which was purified by column chromatography to obtain 8.14 g of the product, with a yield of 62%. MS( m / z ): 438.23[M] + ; 1 H NMR (CDCl 3 ): d 9.72(d, 1H), 8.17(d, 1H), 7.53(d, 1H), 7.39(d, 1H), 4.83(m, 1H), 3.32(m, 2H) 3.15(d, 2H) , 2.24~1.23(m, 18H); Anal. Calcd for C 20 h 27 BrN 2 o 4 : C,54.68; H, 6.19; N,6.38, Found: C,54.62; H, 6.23; ...

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Abstract

The present invention relates to a mitochondrial function protecting agent shown in formula (I), a preparation method therefor and applications thereof to the treatment of Parkinson disease and Alzheimer disease, wherein R1, R2, R3, R4 are independently selected from -NO2, -OH, -F, -CL, -Br, -H, -OCH3 and -CH3; and n=1-9. The mitochondrial function protecting agent provided by the present invention uses triphenyl phosphine cationic as a structural unit, is bound to an antioxidant component (nitroxyl radical unit) by covalent bonds, and drives an entire molecule to be rapidly enriched in the mitochondrion in a potential-dependent manner under the driving of cell membrane potential and mitochondrial membrane potential, thereby realizing mitochondrial targeting of new drug molecules .

Description

technical field [0001] The invention relates to a mitochondrial function protection agent and a preparation method thereof and its application in treating Parkinson's and Alzheimer's diseases, belonging to the technical field of medicine. Background technique [0002] Neurodegenerative diseases are a kind of chronic progressive nervous system degenerative diseases clinically manifested in different degrees of impairment of memory, sensory ability, judgment, thinking ability and motor ability. Such diseases mainly include Alzheimer's disease (that is, senile dementia), Parkinson's disease and spinal muscular atrophy. With the advent of the world's aging population, the incidence of neurodegenerative diseases is increasing year by year. At present, the elderly population over 60 years old in my country has exceeded 120 million, and neurodegenerative diseases have become serious diseases that threaten the health of the elderly. [0003] At present, neurodegenerative diseases ...

Claims

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Application Information

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IPC IPC(8): C07F9/6558A61K31/675A61P25/28A61P25/16
Inventor 王海波高鹏鹿成韬孙晓莉丁桂荣
Owner FOURTH MILITARY MEDICAL UNIVERSITY
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