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带有硝酮自旋捕捉剂的N-芳基吡啶鎓盐的合成作为潜在的线粒体靶向抗氧化剂。

Synthesis of N-arylpyridinium salts bearing a nitrone spin trap as potential mitochondria-targeted antioxidants.

作者信息

Robertson Linsey, Hartley Richard C

机构信息

Centre for the Chemical Research of Ageing, WestCHEM Department of Chemistry, University of Glasgow, Glasgow G12 8QQ, UK.

出版信息

Tetrahedron. 2009 Jul 4;65(27):5284-5292. doi: 10.1016/j.tet.2009.04.083.

DOI:10.1016/j.tet.2009.04.083
PMID:19693262
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2722452/
Abstract

The generation of excess reactive oxygen species (ROS) in mitochondria is responsible for much of the oxidative stress associated with ageing (aging), and mitochondrial dysfunction is part of the pathology of neurodegeneration and type 2 diabetes. Lipophilic pyridinium ions are known to accumulate in mitochondria and this paper describes a general route for the preparation of nitrone-containing N-arylpyridinium salts having a range of lipophilicities, as potential therapeutic antioxidants. The compatibility of nitrones with the Zincke reaction is the key to their synthesis. Their trapping of carbon-centred radicals and the EPR spectra of the resulting nitroxides are reported.

摘要

线粒体中过量活性氧(ROS)的产生是与衰老相关的许多氧化应激的原因,线粒体功能障碍是神经退行性变和2型糖尿病病理学的一部分。已知亲脂性吡啶鎓离子会在线粒体中积累,本文描述了一种制备具有一系列亲脂性的含硝酮N-芳基吡啶鎓盐的通用方法,作为潜在的治疗性抗氧化剂。硝酮与津克反应的相容性是其合成的关键。报道了它们对碳中心自由基的捕获以及所得氮氧化物的电子顺磁共振光谱。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8956/2722452/206107a9e486/gr9.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8956/2722452/95a8d05769b9/fx1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8956/2722452/fbf7e7d10f5f/sc1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8956/2722452/e4e24b334f57/gr1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8956/2722452/14e66ac0aa87/gr2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8956/2722452/1f36ea03ba79/gr3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8956/2722452/5cc2a66ab031/gr4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8956/2722452/97afeab77de9/sc2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8956/2722452/49702954e373/sc3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8956/2722452/e38b1ee71fe0/sc4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8956/2722452/f15bdc1a94a7/sc5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8956/2722452/76812c739af1/sc6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8956/2722452/27c0ebad8677/sc7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8956/2722452/36cd6ccaf101/sc8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8956/2722452/e3c3f73a1439/gr5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8956/2722452/51ed02134ea6/gr6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8956/2722452/4ce28af3ffce/gr7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8956/2722452/af7af0aaf2a8/gr8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8956/2722452/206107a9e486/gr9.jpg

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