Nitrofurazone and its nitroheterocyclic analogues: a study of the electrochemical behavior in aqueous medium

Autor(es)

Brito, Charles de Lima ^[1] ; Goulart Trossini, Gustavo Henrique ^[1] ; Ferreira, Elizabeth Igne ^[1] ; La-Scalea, Mauro Aquiles ^[2]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Fac Ciencias Farmaceut, Dept Farm, Lab Planejamento & Sintese Quimioterap Potencialm, BR-05508000 Sao Paulo - Brazil

^[2] Univ Fed Sao Paulo UNIFESP, Dept Ciencias Exatas & Terra, BR-09972270 Diadema, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of the Brazilian Chemical Society; v. 24, n. 12, p. 1964+, DEC 2013.
• Citações Web of Science: 5

Resumo

The biological action of drugs with potential antichagasic activities can be better understood by knowing their reduction mechanism. For this proposal, the electrochemical reduction of nitrofurazone (NF) and its analogues, nitrofurfurilidene thiosemicarbazone (NFS), nitrothiophene semicarbazone (NT), nitrothiophene thiosemicarbazone (NTS), was studied by differential pulse and cyclic voltammetries and chronoamperometry in aqueous medium by using a glassy carbon electrode. Those three synthetic analogues have oxygen and sulfur atoms arranged between the nitroheterocyclic ring (furan and thiophene, respectively) and the carbonyl group (semicarbazone and thiosemicarbazone, respectively). The respective hydroxylamine derivatives are the main products formed in acidic medium, being its formation linearly pH dependent. Although chronoamperometric data show that this reduction involves 4 electrons, its corresponding reduction voltammetric wave, in alkaline medium, is unfolded and a reversible reduction peak at a more positive potential appears. This peak is characterized as a nitro anion radical formation, whose decay is caused by a disproportionation reaction. Its kinetic stability was studied by the current ratio values of the R - NO2/R - NO2• - redox couple and the second-order constant (k2) was determined, being NTS the analogue that registered the highest stability. (AU)

• Processo FAPESP: 11/11499-0 - Aplicação de bioisosterismo no planejamento de agentes antichagásicos: integração entre estratégias computacionais e experimentais
• Beneficiário: Gustavo Henrique Goulart Trossini
• Modalidade de apoio: Auxílio à Pesquisa - Regular