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Voltammetric Study of Some 3-Aryl-quinoxaline-2-carbonitrile 1,4-di-N-oxide Derivatives with Anti-Tumor Activities

The electrochemical properties of twenty 3-aryl-quinoxaline-2-carbonitrile 1,4-di-N-oxide derivatives with varying degrees of cytotoxic activity were investigated in dimethylformamide (DMF) using cyclic voltammetry and first derivative cyclic voltammetry. With one exception, the first reduction of t...

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Autores principales: Miller, Eric M., Xia, Qing, Cella, Mariah E., Nenninger, Austin W., Mruzik, Monica N., Brillos-Monia, Krystina A., Hu, Yong Zhou, Sheng, Rong, Ragain, Christina M., Crawford, Philip W.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6151727/
https://www.ncbi.nlm.nih.gov/pubmed/28858261
http://dx.doi.org/10.3390/molecules22091442
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author Miller, Eric M.
Xia, Qing
Cella, Mariah E.
Nenninger, Austin W.
Mruzik, Monica N.
Brillos-Monia, Krystina A.
Hu, Yong Zhou
Sheng, Rong
Ragain, Christina M.
Crawford, Philip W.
author_facet Miller, Eric M.
Xia, Qing
Cella, Mariah E.
Nenninger, Austin W.
Mruzik, Monica N.
Brillos-Monia, Krystina A.
Hu, Yong Zhou
Sheng, Rong
Ragain, Christina M.
Crawford, Philip W.
author_sort Miller, Eric M.
collection PubMed
description The electrochemical properties of twenty 3-aryl-quinoxaline-2-carbonitrile 1,4-di-N-oxide derivatives with varying degrees of cytotoxic activity were investigated in dimethylformamide (DMF) using cyclic voltammetry and first derivative cyclic voltammetry. With one exception, the first reduction of these compounds was found to be reversible or quasireversible and is attributed to reduction of the N-oxide moiety to form a radical anion. The second reduction of the diazine ring was found to be irreversible. Compounds containing a nitro group on the 3-phenyl ring also exhibited a reduction process that may be attributed to that group. There was good correlation between molecular structure and reduction potential, with reduction being facilitated by an enhanced net positive charge at the electroactive site created by electron withdrawing substituents. Additionally, the reduction potential was calculated using two common basis sets, 6-31g and lanl2dz, for five of the test molecules. There was a strong correlation between the computational data and the experimental data, with the exception of the derivative containing the nitro functionality. No relationship between the experimentally measured reduction potentials and reported cytotoxic activities was evident upon comparison of the data.
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spelling pubmed-61517272018-11-13 Voltammetric Study of Some 3-Aryl-quinoxaline-2-carbonitrile 1,4-di-N-oxide Derivatives with Anti-Tumor Activities Miller, Eric M. Xia, Qing Cella, Mariah E. Nenninger, Austin W. Mruzik, Monica N. Brillos-Monia, Krystina A. Hu, Yong Zhou Sheng, Rong Ragain, Christina M. Crawford, Philip W. Molecules Article The electrochemical properties of twenty 3-aryl-quinoxaline-2-carbonitrile 1,4-di-N-oxide derivatives with varying degrees of cytotoxic activity were investigated in dimethylformamide (DMF) using cyclic voltammetry and first derivative cyclic voltammetry. With one exception, the first reduction of these compounds was found to be reversible or quasireversible and is attributed to reduction of the N-oxide moiety to form a radical anion. The second reduction of the diazine ring was found to be irreversible. Compounds containing a nitro group on the 3-phenyl ring also exhibited a reduction process that may be attributed to that group. There was good correlation between molecular structure and reduction potential, with reduction being facilitated by an enhanced net positive charge at the electroactive site created by electron withdrawing substituents. Additionally, the reduction potential was calculated using two common basis sets, 6-31g and lanl2dz, for five of the test molecules. There was a strong correlation between the computational data and the experimental data, with the exception of the derivative containing the nitro functionality. No relationship between the experimentally measured reduction potentials and reported cytotoxic activities was evident upon comparison of the data. MDPI 2017-08-31 /pmc/articles/PMC6151727/ /pubmed/28858261 http://dx.doi.org/10.3390/molecules22091442 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Miller, Eric M.
Xia, Qing
Cella, Mariah E.
Nenninger, Austin W.
Mruzik, Monica N.
Brillos-Monia, Krystina A.
Hu, Yong Zhou
Sheng, Rong
Ragain, Christina M.
Crawford, Philip W.
Voltammetric Study of Some 3-Aryl-quinoxaline-2-carbonitrile 1,4-di-N-oxide Derivatives with Anti-Tumor Activities
title Voltammetric Study of Some 3-Aryl-quinoxaline-2-carbonitrile 1,4-di-N-oxide Derivatives with Anti-Tumor Activities
title_full Voltammetric Study of Some 3-Aryl-quinoxaline-2-carbonitrile 1,4-di-N-oxide Derivatives with Anti-Tumor Activities
title_fullStr Voltammetric Study of Some 3-Aryl-quinoxaline-2-carbonitrile 1,4-di-N-oxide Derivatives with Anti-Tumor Activities
title_full_unstemmed Voltammetric Study of Some 3-Aryl-quinoxaline-2-carbonitrile 1,4-di-N-oxide Derivatives with Anti-Tumor Activities
title_short Voltammetric Study of Some 3-Aryl-quinoxaline-2-carbonitrile 1,4-di-N-oxide Derivatives with Anti-Tumor Activities
title_sort voltammetric study of some 3-aryl-quinoxaline-2-carbonitrile 1,4-di-n-oxide derivatives with anti-tumor activities
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6151727/
https://www.ncbi.nlm.nih.gov/pubmed/28858261
http://dx.doi.org/10.3390/molecules22091442
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