Cyclic voltammetric study of some anti-Chagas-active 1,4-dioxidoquinoxalin-2-yl ketone derivatives
The electrochemical properties of 24 1,4-dioxidoquinoxalin-2-yl ketone derivatives with varying degrees of anti-Chagas activity were investigated in the aprotic solvent dimethylformamide (DMF) by cyclic voltammetry and first-derivative cyclic voltammetry. For this group of compounds, the first re...
| Main Authors: | , , , , , , |
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| Format: | info:eu-repo/semantics/article |
| Language: | eng |
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Wiley
2014
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| Online Access: | https://hdl.handle.net/10171/35792 |
| _version_ | 1793400193468596224 |
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| author | Crawford, P.W. (Philip W.) Monge, A. (Antonio) Aldana, I. (Ignacio) Moreno-de-Viguri, E. (Elsa) Torres, E. (Enrique) Devarapally, G. (Goutham) Peres-Silanes, S. (Silvia) |
| author_facet | Crawford, P.W. (Philip W.) Monge, A. (Antonio) Aldana, I. (Ignacio) Moreno-de-Viguri, E. (Elsa) Torres, E. (Enrique) Devarapally, G. (Goutham) Peres-Silanes, S. (Silvia) |
| author_sort | Crawford, P.W. (Philip W.) |
| collection | DSpace |
| description | The electrochemical properties of 24 1,4-dioxidoquinoxalin-2-yl ketone derivatives with varying
degrees of anti-Chagas activity were investigated in the aprotic solvent dimethylformamide (DMF) by
cyclic voltammetry and first-derivative cyclic voltammetry. For this group of compounds, the first
reduction in DMF was either reversible or quasireversible and consistent with reduction of the N-oxide
functionality to form the radical anion. The second reduction process for these compounds was
irreversible under the conditions used. The reduction potentials correlated well with molecular structure.
Substitution in the 3-, 6-, and 7- positions of the quinoxaline ring by electron-withdrawing substituents
directly affected the ease of reduction and improved the biological activities of these compounds,
whereas substitution by electron-donating groups had the opposite effect. The electrochemical results,
when combined with previous work on their mechanism of action against Chagas disease and their
measured anti-Chagas activities, indicated that the quinoxaline 1,4-dioxide system serves as a promising
starting point for chemical modifications aimed at improving the T. cruzi activity via a possible
bioreduction mechanism. |
| format | info:eu-repo/semantics/article |
| id | oai:dadun.unav.edu:10171-35792 |
| institution | Universidad de Navarra |
| language | eng |
| publishDate | 2014 |
| publisher | Wiley |
| record_format | dspace |
| spelling | oai:dadun.unav.edu:10171-357922020-03-04T00:23:01Z Cyclic voltammetric study of some anti-Chagas-active 1,4-dioxidoquinoxalin-2-yl ketone derivatives Crawford, P.W. (Philip W.) Monge, A. (Antonio) Aldana, I. (Ignacio) Moreno-de-Viguri, E. (Elsa) Torres, E. (Enrique) Devarapally, G. (Goutham) Peres-Silanes, S. (Silvia) Voltammetric Study Quinoxaline Quinoxaline 1,4-di-N-oxide Chagas The electrochemical properties of 24 1,4-dioxidoquinoxalin-2-yl ketone derivatives with varying degrees of anti-Chagas activity were investigated in the aprotic solvent dimethylformamide (DMF) by cyclic voltammetry and first-derivative cyclic voltammetry. For this group of compounds, the first reduction in DMF was either reversible or quasireversible and consistent with reduction of the N-oxide functionality to form the radical anion. The second reduction process for these compounds was irreversible under the conditions used. The reduction potentials correlated well with molecular structure. Substitution in the 3-, 6-, and 7- positions of the quinoxaline ring by electron-withdrawing substituents directly affected the ease of reduction and improved the biological activities of these compounds, whereas substitution by electron-donating groups had the opposite effect. The electrochemical results, when combined with previous work on their mechanism of action against Chagas disease and their measured anti-Chagas activities, indicated that the quinoxaline 1,4-dioxide system serves as a promising starting point for chemical modifications aimed at improving the T. cruzi activity via a possible bioreduction mechanism. 2014-04-12T17:32:38Z 2014-04-12T17:32:38Z 2013-02 info:eu-repo/semantics/article https://hdl.handle.net/10171/35792 eng PIUNA project from de University of Navarra FIMA (Fundacion para la Investigacion Medica Aplicada) from the University of Navarra. info:eu-repo/semantics/openAccess application/pdf Wiley |
| spellingShingle | Voltammetric Study Quinoxaline Quinoxaline 1,4-di-N-oxide Chagas Crawford, P.W. (Philip W.) Monge, A. (Antonio) Aldana, I. (Ignacio) Moreno-de-Viguri, E. (Elsa) Torres, E. (Enrique) Devarapally, G. (Goutham) Peres-Silanes, S. (Silvia) Cyclic voltammetric study of some anti-Chagas-active 1,4-dioxidoquinoxalin-2-yl ketone derivatives |
| title | Cyclic voltammetric study of some anti-Chagas-active 1,4-dioxidoquinoxalin-2-yl ketone derivatives |
| title_full | Cyclic voltammetric study of some anti-Chagas-active 1,4-dioxidoquinoxalin-2-yl ketone derivatives |
| title_fullStr | Cyclic voltammetric study of some anti-Chagas-active 1,4-dioxidoquinoxalin-2-yl ketone derivatives |
| title_full_unstemmed | Cyclic voltammetric study of some anti-Chagas-active 1,4-dioxidoquinoxalin-2-yl ketone derivatives |
| title_short | Cyclic voltammetric study of some anti-Chagas-active 1,4-dioxidoquinoxalin-2-yl ketone derivatives |
| title_sort | cyclic voltammetric study of some anti-chagas-active 1,4-dioxidoquinoxalin-2-yl ketone derivatives |
| topic | Voltammetric Study Quinoxaline Quinoxaline 1,4-di-N-oxide Chagas |
| url | https://hdl.handle.net/10171/35792 |
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