JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 65 No 1 (2020): Journal of the Chilean Chemical Society
Original Research Papers

ELECTROCHEMICAL, ESR, THEORETICAL STUDIES AND IN VITRO ANTI–T. CRUZI ACTIVITY OF 2-ORGANOMETALLIC-5-NITRO-BENZIMIDAZOLES

Germán Barriga-González
Universidad Metropolitana de Ciencias de la Educación
Carla Olivares-Petit
Universidad Metropolitana de Ciencias de la Educación
Patricia Toro
Pontificia Universidad Católica de Valparaíso
A. Hugo Klahn
Pontificia Universidad Católica de Valparaíso
Claudio Olea-Azar
Universidad de Chile
Juan D. Maya
Universidad de Chile
Yosselin Huentupil
Universidad de Concepción
Rodrigo Arancibia
Universidad de Concepción
Published March 8, 2020
Keywords
  • Organometallic-benzimidazoles,
  • Cyclic voltammetry,
  • ESR,
  • Trypanocidal activity,
  • computational calculations,
  • DFT
  • ...More
    Less

Abstract

The bioorganometallic compounds 2-cyrhetrenyl-5-nitro-benzimidazole (Bzn-1) and 2-ferrocenyl-5-nitro-benzimidazole (Bzn-2) have been proposed as potential anti-Trypanosoma cruzi agents. On this regard, electrochemical, electron spin resonance and biological studies were carried out. Cyclic voltammetry experiments showed the generation of nitro anion radical derivatives and a self-protonation process was observed. Nitro anion radicals generated were characterized and analyzed using electron spin resonance spectroscopy. The compounds were tested in vitro against Trypanosoma cruzi (Dm28c strain). Biological evaluation display that 2-cyrhetrenyl-5-nitro-benzimidazole (Bzn-1) was more active than its ferrocene analogue (Bzn-2) and purely organic derivate (Bzn-3), associated with the electron-withdrawing properties of the (η5-C5H4)Re(CO)3 moiety. Finally, theoretical studies were carried out in order to elucidate the correlation between organometallic fragment, nitro-reduction potentials and trypanocidal activity.

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