Nitro radical anion formation from nitrofuryl substituted 1,4-dihydropyridine derivatives in mixed and non-aqueous media.
Three new nitrofuryl substituted 1,4-dihydropyridine derivatives were electrochemically tested in the scope of newly found compounds useful as chemotherapeutic alternative to the Chagas' disease. All the compounds were capable to produce nitro radical anions sufficiently stabilized in the time window of the cyclic voltammetric experiment. In order to quantify the stability of the nitro radical anion we have calculated the decay constant, k2. Furthermore, from the voltammetric results, some parameters of biological significance as E7(1) (indicative of in vivo nitro radical anion formation) and KO2 (thermodynamic indicator of oxygen redox cycling) have been calculated. From the comparison of E7(1), KO2 and k2 values between the studied nitrofuryl 1,4-DHP derivatives and well-known current drugs an auspicious activity for one of the studied compounds i.e. FDHP2, can be expected.
Argüello
J
J
Bioelectrochemistry Laboratory, Chemical and Pharmaceutical Sciences Faculty, University of Chile, POB 233, Santiago 1, Chile.
Núñez-Vergara
L J
LJ
Bollo
S
S
Squella
J A
JA
D000838:Anions / Q000138:chemical synthesis / Q000737:chemistry; D004095:Dihydropyridines / Q000737:chemistry*; D004563:Electrochemistry; D005609:Free Radicals / Q000138:chemical synthesis / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D015394:Molecular Structure; D009525:Niacin / Q000031:analogs & derivatives* / Q000737:chemistry; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009581:Nitrofurans / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*
C514683:3,5-dicyano-4-(5'-nitro-2'-furyl)-2,6-dimethyl-1,4-dihydropyridine; D000838:Anions; D004095:Dihydropyridines; D005609:Free Radicals; D009574:Nitro Compounds; D009581:Nitrofurans; D000644:Quaternary Ammonium Compounds; C514733:ethyl 3-cyano-4-(5'-nitro-2'-furyl)-2,6-dimethyl-1,4-dihydropyridine-5-carboxylate; C514682:ethyl 4-(5'-nitro-2'-furyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; D009525:Niacin; C038806:1,4-dihydropyridine; C009405:tetrabutylammonium