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Neuroprotective multifunctional antioxidants and their monofunctional analogs

一种抗氧化剂、神经保护的技术，应用在抗毒剂、神经系统疾病、神经肌肉系统疾病等方向，能够解决氧化损害等问题

Active Publication Date: 2016-03-23
彼得 F 卡罗
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

An increase in free ferrous ions can lead to oxidative damage

Method used

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  • Neuroprotective multifunctional antioxidants and their monofunctional analogs
  • Neuroprotective multifunctional antioxidants and their monofunctional analogs
  • Neuroprotective multifunctional antioxidants and their monofunctional analogs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] N-Benzyl-4,6-dimethoxypyrimidin-2-amine

[0067] (compound 28)

[0068] 2-Chloro-4,6-dimethoxypyrimidine (27) (50.0g, 0.29mol), BnNH 2 (93.3ml, 0.85mol) and potassium carbonate (2.5g, 0.45mol) in dioxane (1.0L) was refluxed for 4 days. The reaction was filtered and the filtrate was concentrated in vacuo to give a yellow oil, which was then purified by silica gel column chromatography with 20:1 to 10:1 hexane:EtOAc to yield 61.7 g (87%) of 28 as a white solid. 1 HNMR (CDCL 3 ) δ 7.36-7.27 (m, 5H), 5.42 (s, 1H), 5.25 (s, 1H), 4.61 (d, J=5.86Hz, 2H), 3.83 (s, 6H).

Embodiment 2

[0070] 2-amino-4,6-dimethoxypyrimidine

[0071] (compound 22)

[0072] Compound 28 (27.0 g, 0.11 mol) in 400 ml MeOH was dissolved in 5.4 g 20% ​​Pd(OH 2 ) hydrogenation at room temperature for 2 days in the presence of a catalyst. After filtration and solvent evaporation, after silica gel column chromatography by using compound 22 in 50:1 CHCl 3 : 16.8 g*98% from MeOH) to obtain a white solid. 1 HNMR (CDCL 3 ) δ 5.47 (s, 1H, 4.90 (s, 2H), 3.84 (s.6H).

Embodiment 3

[0074] Synthesis of HK-1, HK-3, HK-5, and HK-7

[0075] The following describes l-(2-pyrimidinyl)pyrrolidine-2,5-dione (HK-1), l-(4,6-dimethoxy-2-pyrimidinyl)pyrrolidine-2,5 -Diketone (HK-3), l-(2-pyrimidinyl)piperidine-2,6-dione (HK-5), l-(4,6-dimethoxy-2-pyrimidinyl)piperidine Pyridine-2,6-dione (HK-7), l-(5-benzyloxy-2-pyrimidinyl)pyrrolidine-2,5 (compound 23), l-(5-benzyloxy-2-pyrimidinyl) piperidine-2,6-dione (compound 24), l-(4,6-dimethoxy-5 benzyloxy-2 pyrimidinyl)pyrrolidine-2,5-dione (compound 25), and l - General synthesis of (4,6-dimethoxy-5benzyloxy-2-pyrimidinyl)piperidine-2,6-dione (compound 26).

[0076] refer to image 3 , 42.0g (0.42mol) of succinic anhydride (17) was dissolved in 300ml of toluene, 200ml of acetone dissolved with 20g (0.21mol) of 2-aminopyrimidine (21) was added, and the mixture was heated to 85°C for 3 days. After cooling to (room temperature) the product precipitated, filtered and washed with toluene. The filtrate was dried under vacuum...

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Abstract

The neuroprotective multifunctional antioxidants are compounds that contain a 2-diacetylamino-5-hydroxypyrimidine moiety, having the structural formula: wherein R1 is CH2 or C2H4; R2 is H or -OR4 where R4 is H or aryl; and R3a and R3b are independently selected from the group consisting of H and -O-alkyl. The antioxidants are orally bioavailable metal-attenuating multifunctional antioxidants that can independently attenuate transition metals, as well as scavenger free radicals. The multifunctional antioxidant compounds, by their ability to independently chelate metals, such as Fe, Cu or Zn, and scavenge free radicals generated from different sources, are neuroprotective and are beneficial for the treatment of various neurological disorders, such as Alzheimer's disease, Parkinson's disease, ALS, traumatic brain injury, ocular disorders, such as cataract, glaucoma, age-related macular degeneration and other retinal degeneration, as well as for reducing the progression of diabetic complications.

Description

technical field [0001] The present invention relates to an antioxidant, in particular to neuroprotective multifunctional antioxidants, which can not only chelate metals (such as iron, copper or zinc), but also scavenge free radicals. The present invention also relates to antioxidant monofunctional analogs of neuroprotective multifunctional antioxidant compounds. The multifunctional compound can be taken orally and can pass through the blood-brain barrier, so the multifunctional compound has a single function on various neurological diseases (for example, Alzheimer's disease, Parkinson's disease, ALS (muscle atrophy side cord sclerosis), traumatic brain injury, eye diseases (eg, cataracts, glaucoma, age-related macular degeneration, and other retinal degenerations), and in reducing the development of diabetic complications. Background technique [0002] Oxidative damage is a hallmark of neurodegenerative diseases. Oxidative stress is caused by reactive oxygen species (ROS),...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/506C07D403/04C07D401/04A61P25/00A61P39/06
CPCA61P3/10A61P21/02A61P25/00A61P25/16A61P25/28A61P27/02A61P27/06A61P27/12A61P39/06C07D239/42C07D239/47C07D239/52C07D239/60C07D401/04C07D403/04
Inventor 彼得·F·卡罗
Owner 彼得 F 卡罗
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