In vivo trypanosomicidal activity of imidazole- or pyrazole-based benzo[g]phthalazine derivatives against acute and chronic phases of Chagas disease

  • J Med Chem. 2011 Feb 24;54(4):970-9. doi: 10.1021/jm101198k.
Manuel Sánchez-Moreno  1 ,  Ana M Sanz ,  Fernando Gómez-Contreras ,  Pilar Navarro ,  Clotilde Marín ,  Inmaculada Ramírez-Macias ,  María Jose Rosales ,  Francisco Olmo ,  Isabel Garcia-Aranda ,  Lucrecia Campayo ,  Carmen Cano ,  Francisco Arrebola ,  María J R Yunta
Affiliations
  • 1. Instituto de Biotecnología, Facultad de Ciencias, Universidad de Granada, 18071 Granada, Spain. [email protected]
Abstract

The in vivo trypanosomicidal activity of the imidazole-based benzo[g]phthalazine derivatives 1-4 and of the new related pyrazole-based compounds 5 and 6 has been studied in both the acute and chronic phases of Chagas disease. As a rule, compounds 1-6 were more active and less toxic than benznidazole in the two stages of the disease, and the monosubstituted derivatives 2, 4, and 6 were more effective than their disubstituted analogs. Feasible mechanisms of action of compounds 1-6 against the Parasite have been explored by considering their inhibitory effect on the Fe-SOD enzyme, the nature of the excreted metabolites and the ultrastructural alterations produced. A complementary histopathological analysis has confirmed that the monosubstituted derivatives are less toxic than the reference drug, with the behavior of the imidazole-based compound 4 being especially noteworthy.