Antiplasmodial and Leishmanicidal Activities of 2-Cyano-3-(4-phenylpiperazine-1-carboxamido) Quinoxaline 1,4-Dioxide Derivatives
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Pharmacology and Structure-Activity Relationship
Compd. | MW | R 6 | R 7 | R 2' | R 4' | IC50 (µM) a | IC50 (µM) b | CC50 (µM) c | SI d |
---|---|---|---|---|---|---|---|---|---|
1 | 537.5 | H | Cl | NO2 | CF3 | 24.5 | 21.8 | 7.0 | 0.3 |
2 | 517 | H | CH3 | NO2 | CF3 | 44.7 | 36.3 | 17.7 | 0.5 |
3 | 521 | H | F | NO2 | CF3 | 14.6 | 41.1 | 11.0 | 0.3 |
4 | 572 | Cl | Cl | NO2 | CF3 | 13.9 | 22.7 | 1.6 | 0.1 |
5 | 492.5 | H | Cl | H | CF3 | 18.6 | 7.6 | 6.4 | 0.8 |
6 | 472 | H | CH3 | H | CF3 | 30.5 | 23.3 | 12.1 | 0.5 |
7 | 476 | H | F | H | CF3 | 30.9 | 28.8 | 12.2 | 0.4 |
8 | 527 | Cl | Cl | H | CF3 | 18.5 | 5.7 | 2.2 | 0.4 |
9 | 422 | H | CH3 | H | F | 36.3 | 23.0 | 24.1 | 1.1 |
10 | 426 | H | F | H | F | 34.3 | 31.3 | 24.3 | 0.8 |
11 | 454.5 | H | Cl | H | CH3O | 12.8 | 18.8 | 47.5 | 2.5 |
12 | 434 | H | CH3 | H | CH3O | 30.4 | 30.0 | 183.5 | 6.1 |
13 | 489 | Cl | Cl | H | CH3O | 26.1 | 10.9 | 14.0 | 1.3 |
CQ | 320 | 0.1 | |||||||
DOX | 543.5 | 6.4 | 0.4 | >10 |
3. Experimental
3.1. Chemical Synthesis
3.1.1. General Remarks
3.1.2. General Procedure for the Synthesis of Cyanoamines II
3.1.3. General Procedure for the Synthesis of 2-Cyano-3-(4-phenylpiperazine-1-carboxamido) Quinoxaline 1,4-Dioxide (CPCQs)
3.2. Pharmacology
3.2.1. In Vitro Antiplasmodial Drug Assay
3.2.2. In Vitro Cytotoxicity
3.2.3.In Vitro Antileishmanial Drug Assay
4. Conclusions
Acknowledgments
References
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Barea, C.; Pabón, A.; Galiano, S.; Pérez-Silanes, S.; Gonzalez, G.; Deyssard, C.; Monge, A.; Deharo, E.; Aldana, I. Antiplasmodial and Leishmanicidal Activities of 2-Cyano-3-(4-phenylpiperazine-1-carboxamido) Quinoxaline 1,4-Dioxide Derivatives. Molecules 2012, 17, 9451-9461. https://doi.org/10.3390/molecules17089451
Barea C, Pabón A, Galiano S, Pérez-Silanes S, Gonzalez G, Deyssard C, Monge A, Deharo E, Aldana I. Antiplasmodial and Leishmanicidal Activities of 2-Cyano-3-(4-phenylpiperazine-1-carboxamido) Quinoxaline 1,4-Dioxide Derivatives. Molecules. 2012; 17(8):9451-9461. https://doi.org/10.3390/molecules17089451
Chicago/Turabian StyleBarea, Carlos, Adriana Pabón, Silvia Galiano, Silvia Pérez-Silanes, German Gonzalez, Chloe Deyssard, Antonio Monge, Eric Deharo, and Ignacio Aldana. 2012. "Antiplasmodial and Leishmanicidal Activities of 2-Cyano-3-(4-phenylpiperazine-1-carboxamido) Quinoxaline 1,4-Dioxide Derivatives" Molecules 17, no. 8: 9451-9461. https://doi.org/10.3390/molecules17089451