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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...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2017
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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. |
format | Online Article Text |
id | pubmed-6151727 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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