Artículo de revista
Voltammetric redox behavior of nitrofuryl 1,4-dihydropyridine derivatives: Interdependence between two redox centers
Fecha
2006-06-01Registro en:
JOURNAL OF ELECTROANALYTICAL CHEMISTRY 591(1): 99-104
0022-0728
Autor
Argüello da Silva, Jacqueline
Núñez Vergara, Luis
Bollo Dragnic, Soledad
Squella Serrano, Juan
Institución
Resumen
To investigate new chemotherapeutics alternatives to Chagas' disease, three 4-(5'-nitro-2'-furyl)-1,4-dihydropyridine derivatives were synthesized and electrochemically investigated in order to clarify their redox behavior. The redox behavior of these compounds is very attractive as they share a reducible (nitrofuryl) and an oxidizable (1,4-DHP) moiety, the interdependence of these two redox centers will be our current challenge. The reduction of the nitrofuryl derivatives was studied in two different protogenic aqueous-organic media (Britton-Robinson buffer/ethanol: 70/30 and citrate buffer/DMF: 60/40) and working at two different experimental time windows (i.e., Polarographic and cyclic voltammetric experiments). The current work reveals that both redox centers showed a great interdependence and electronic communication, determining its electrochemical properties. The reduction potential of the nitrofuryl moiety can be modulated at both fine tuning (tens of mV) by changing the electronic properties of the 3,5 substituents in the 1,4-DHP ring, and coarse tuning (cents of mV) by changing the oxidation state of the 1,4-DHP ring into a pyridine ring, thus producing nitrofuryl derivatives with very low reduction potentials, i.e., good candidates to be reduced by nitroreductases.