1,4-Di-N-oxide quinoxaline-2-carboxamide: Cyclic voltammetry and relationship between electrochemical behavior, structure and anti-tuberculosis activity
To gain insight into the mechanism of action, the redox properties of 37 quinoxaline-2-carboxamide 1,4-di-N-oxides with varying degrees of anti-tuberculosis activity were studied in dimethylformamide (DMF) using cyclic voltammetry and first derivative cyclic voltammetry. For all compounds studied, e...
| Main Authors: | , , , , , , , , |
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| Format: | info:eu-repo/semantics/article |
| Language: | eng |
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Elsevier
2011
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10171/18731 |
| _version_ | 1793400187666825216 |
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| author | Moreno-de-Viguri, E. (Elsa) Pérez-Silanes, S. (Silvia) Gouravaram, S. (S.) Macharam, A. (Abinav) Ancizu, S. (Saioa) Torres, E. (Enrique) Aldana, I. (Ignacio) Monge, A. (Antonio) Crawford, P.W. (Philip W.) |
| author_facet | Moreno-de-Viguri, E. (Elsa) Pérez-Silanes, S. (Silvia) Gouravaram, S. (S.) Macharam, A. (Abinav) Ancizu, S. (Saioa) Torres, E. (Enrique) Aldana, I. (Ignacio) Monge, A. (Antonio) Crawford, P.W. (Philip W.) |
| author_sort | Moreno-de-Viguri, E. (Elsa) |
| collection | DSpace |
| description | To gain insight into the mechanism of action, the redox properties of 37 quinoxaline-2-carboxamide 1,4-di-N-oxides with varying degrees of anti-tuberculosis activity were studied in dimethylformamide (DMF) using cyclic voltammetry and first derivative cyclic voltammetry. For all compounds studied, electrochemical reduction in DMF is consistent with the reduction of the N-oxide functionality to form a radical anion. The influence of molecular structure on reduction potential is addressed and it can be said that a general relationship exists between reduction potential and reported antimicrobial activity. For those compounds which have demonstrated promising biological activity, the more active the compound the less negative the reduction potential typically is. The results suggest the possible participation of charge transfer processes in the mechanism of action of quinoxaline di-N-oxides against tuberculosis and offer new insights into the design of future antitubercular drugs. |
| format | info:eu-repo/semantics/article |
| id | oai:dadun.unav.edu:10171-18731 |
| institution | Universidad de Navarra |
| language | eng |
| publishDate | 2011 |
| publisher | Elsevier |
| record_format | dspace |
| spelling | oai:dadun.unav.edu:10171-187312020-03-04T06:15:55Z 1,4-Di-N-oxide quinoxaline-2-carboxamide: Cyclic voltammetry and relationship between electrochemical behavior, structure and anti-tuberculosis activity Moreno-de-Viguri, E. (Elsa) Pérez-Silanes, S. (Silvia) Gouravaram, S. (S.) Macharam, A. (Abinav) Ancizu, S. (Saioa) Torres, E. (Enrique) Aldana, I. (Ignacio) Monge, A. (Antonio) Crawford, P.W. (Philip W.) Electrochemical behavior Anti-tuberculosis activity Cyclic voltammetry To gain insight into the mechanism of action, the redox properties of 37 quinoxaline-2-carboxamide 1,4-di-N-oxides with varying degrees of anti-tuberculosis activity were studied in dimethylformamide (DMF) using cyclic voltammetry and first derivative cyclic voltammetry. For all compounds studied, electrochemical reduction in DMF is consistent with the reduction of the N-oxide functionality to form a radical anion. The influence of molecular structure on reduction potential is addressed and it can be said that a general relationship exists between reduction potential and reported antimicrobial activity. For those compounds which have demonstrated promising biological activity, the more active the compound the less negative the reduction potential typically is. The results suggest the possible participation of charge transfer processes in the mechanism of action of quinoxaline di-N-oxides against tuberculosis and offer new insights into the design of future antitubercular drugs. 2011-07-04T18:10:07Z 2011-07-04T18:10:07Z 2011 info:eu-repo/semantics/article https://hdl.handle.net/10171/18731 eng info:eu-repo/semantics/openAccess application/pdf Elsevier |
| spellingShingle | Electrochemical behavior Anti-tuberculosis activity Cyclic voltammetry Moreno-de-Viguri, E. (Elsa) Pérez-Silanes, S. (Silvia) Gouravaram, S. (S.) Macharam, A. (Abinav) Ancizu, S. (Saioa) Torres, E. (Enrique) Aldana, I. (Ignacio) Monge, A. (Antonio) Crawford, P.W. (Philip W.) 1,4-Di-N-oxide quinoxaline-2-carboxamide: Cyclic voltammetry and relationship between electrochemical behavior, structure and anti-tuberculosis activity |
| title | 1,4-Di-N-oxide quinoxaline-2-carboxamide: Cyclic voltammetry and relationship between electrochemical behavior, structure and anti-tuberculosis activity |
| title_full | 1,4-Di-N-oxide quinoxaline-2-carboxamide: Cyclic voltammetry and relationship between electrochemical behavior, structure and anti-tuberculosis activity |
| title_fullStr | 1,4-Di-N-oxide quinoxaline-2-carboxamide: Cyclic voltammetry and relationship between electrochemical behavior, structure and anti-tuberculosis activity |
| title_full_unstemmed | 1,4-Di-N-oxide quinoxaline-2-carboxamide: Cyclic voltammetry and relationship between electrochemical behavior, structure and anti-tuberculosis activity |
| title_short | 1,4-Di-N-oxide quinoxaline-2-carboxamide: Cyclic voltammetry and relationship between electrochemical behavior, structure and anti-tuberculosis activity |
| title_sort | 1,4-di-n-oxide quinoxaline-2-carboxamide: cyclic voltammetry and relationship between electrochemical behavior, structure and anti-tuberculosis activity |
| topic | Electrochemical behavior Anti-tuberculosis activity Cyclic voltammetry |
| url | https://hdl.handle.net/10171/18731 |
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