Synthesis and Reduction Kinetics of Sterically Shielded Pyrrolidine Nitroxides

被引：125

作者：

Paletta, Joseph T. ^{[1
]}

Pink, Maren ^{[2
]}

Foley, Bridget ^{[1
]}

Rajca, Suchada ^{[1
]}

Rajca, Andrzej ^{[1
]}

机构：

[1] Univ Nebraska, Dept Chem, Lincoln, NE 68588 USA

[2] Indiana Univ, Dept Chem, IUMSC, Bloomington, IN 47405 USA

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 20期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

ASCORBIC-ACID; SPIN-LABEL; RESONANCE; AGENTS;

D O I：

10.1021/ol302506f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of sterically shielded pyrrolidine nitroxides were synthesized, and their reduction by ascorbate (vitamin C) indicate that nitroxide 3, a tetraethyl derivative of 3-carboxy-PROXYL, is reduced at the slowest rate among known nitroxides, i.e., at a 60-fold slower rate than that for 3-carboxy-PROXYL.

引用

收藏

页码：5322 / 5325

页数：4

相关论文

共 30 条

[1]

[Anonymous], J CHEM SOC REV

[2] Synthesis of novel bicyclic nitroxides using partial favorskii rearrangement [J].

Babic, Andrej ;

Pecar, Slavko .

SYNLETT, 2008, (08) :1155-1158

[3] MECHANISM OF DISPROPORTIONATION OF ASCORBATE RADICALS [J].

BIELSKI, BHJ ;

ALLEN, AO ;

SCHWARZ, HA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (12) :3516-3518

[4] Reversible reduction of nitroxides to hydroxylamines: Roles for ascorbate and glutathione [J].

Bobko, Andrey A. ;

Kirilyuk, Igor A. ;

Grigor'ev, Igor A. ;

Zweier, Jav L. ;

Khramtsov, Valery V. .

FREE RADICAL BIOLOGY AND MEDICINE, 2007, 42 (03) :404-412

[5] The Effect of Structure on Nitroxide EPR Spectral Linewidth [J].

Burks, Scott R. ;

Makowsky, Mallory A. ;

Yaffe, Zachary A. ;

Hoggle, Chad ;

Tsai, Pei ;

Muralidharan, Sukumaran ;

Bowman, Michael K. ;

Kao, Joseph P. Y. ;

Rosen, Gerald M. .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (14) :4737-4741

[6]

CELLA JA, 1974, J CHEM SOC CHEM COMM, P943

[7] Synthesis of a BDPA-TEMPO Biradical [J].

Dane, Eric L. ;

Maly, Thorsten ;

Debelouchina, Galia T. ;

Griffin, Robert G. ;

Swager, Timothy M. .

ORGANIC LETTERS, 2009, 11 (09) :1871-1874

[8] A novel nitroxide is an effective brain redox imaging contrast agent and in vivo radioprotector [J].

Davis, Ryan M. ;

Sowers, Anastasia L. ;

DeGraff, William ;

Bernardo, Marcelino ;

Thetford, Angela ;

Krishna, Murali C. ;

Mitchell, James B. .

FREE RADICAL BIOLOGY AND MEDICINE, 2011, 51 (03) :780-790

[9] A novel ascorbic acid-resistant nitroxide in fat emulsion is an efficient brain imaging probe for in vivo EPR imaging of mouse [J].

Emoto, Miho ;

Mito, Fumiya ;

Yamasaki, Toshihide ;

Yamada, Ken-Ichi ;

Sato-Akaba, Hideo ;

Hirata, Hiroshi ;

Fujii, Hirotada .

FREE RADICAL RESEARCH, 2011, 45 (11-12) :1325-1332

[10]

Frisch M. J., 2016, Gaussian 03 Revision B.03