Theoretical and voltammetric studies of 5-Nitro-heterocyclic derivatives with potential trypanocidal activities

Autor(es)

Paula, Favero R. ^{[1, 2]} ; Trossini, Gustavo H. G. ^[3] ; Ferreira, Elizabeth I. ^[3] ; Serrano, Silvia H. P. ^[4] ; Menezes, Carla M. S. ^[3] ; Tavares, Leoberto C. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Dept Biochem Pharmaceut Technol, BR-05508900 Sao Paulo - Brazil

^[2] State Univ W Ctr Parana, Dept Pharm, BR-85040080 Guarapuava, PR - Brazil

^[3] Univ Sao Paulo, Dept Pharm, Fac Pharmaceut Sci, BR-05508900 Sao Paulo - Brazil

^[4] Univ Sao Paulo, Inst Chem, BR-05508900 Sao Paulo - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of the Brazilian Chemical Society; v. 21, n. 4, p. 740-749, 2010.
• Citações Web of Science: 5

Resumo

Stereoelectronic properties of nitro-heterocyclic bioisosteric congeners were investigated using theory-level quantum chemistry and cyclic voltammetry with the goal of determining physico-chemical properties that affect the redox potential of the nitro group. Molecular geometry, physicochemical properties and stereoelectronic surfaces, such as molecular electrostatic potential, and HOMO and LUMO orbitalar distributions, were calculated using the AM1 semiempirical method. The redox potential of nitro-heterocyclic compounds, which corresponds to the (Ar-NO2/Ar-NO2•- ) redox couple, was measured in aprotic media (DMSO and 0.1 mol L-1 Bu4NH4BF4) using glassy carbon as working electrode, Pt wire, Ag/AgCl, KCl(sat) as counter and reference electrodes, respectively. Analysis of minimal energy conformers of all derivatives indicated a break in structural planarity located between the hydrazine nitrogen and benzamide moiety. No statistical correlation was obtained using the PLS regression method, taking in account all physicochemical properties and the redox potential, which might result from the lack of coplanarity effect in the molecular structure of the compounds. (AU)

• Processo FAPESP: 01/01192-3 - Antichagásicos potenciais derivados de compostos nitro-heterocíclicos
• Beneficiário: Elizabeth Igne Ferreira
• Modalidade de apoio: Auxílio à Pesquisa - Temático