title: Novel antiprotozoal products: imidazole and benzimidazole N-oxide derivatives and related compounds.
abstract: The syntheses and biological evaluation of the first anti-protozoa imidazole N-oxide and benzimidazole N-oxide and their derivatives are reported. They were tested in vitro against two different protozoa, Trypanosoma cruzi and Trichomonas vaginalis. Derivative 7c, ethyl-1-(i-butyloxycarbonyloxy)-6-nitrobenzimid-azole-2-carboxylate, displayed activity on both protozoa. Lipophilicity and redox potential were experimentally determined in order to study the relationship with activity of the compounds. These properties are well related with the observed bioactivity. Imidazole and benzimidazole N-oxide derivatives are becoming leaders for further chemical modifications and advanced biological studies.
authors.affiliation: Departamento de Química Orgánica, Facultad de Química-Facultad de Ciencias, Montevideo, Uruguay.
authors.forename: Gabriela
authors.initials: G
authors.lastname: Aguirre
authors.forename: Mariana
authors.initials: M
authors.lastname: Boiani
authors.forename: Hugo
authors.initials: H
authors.lastname: Cerecetto
authors.forename: Alejandra
authors.initials: A
authors.lastname: Gerpe
authors.forename: Mercedes
authors.initials: M
authors.lastname: González
authors.forename: Yolanda Fernández
authors.initials: YF
authors.lastname: Sainz
authors.forename: Ana
authors.initials: A
authors.lastname: Denicola
authors.forename: Carmen Ochoa
authors.initials: CO
authors.lastname: De Ocáriz
authors.forename: Juan José
authors.initials: JJ
authors.lastname: Nogal
authors.forename: David
authors.initials: D
authors.lastname: Montero
authors.forename: José Antonio
authors.initials: JA
authors.lastname: Escario
mesh_terms: D000818:Animals; D000981:Antiprotozoal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003497:Cyclic N-Oxides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015195:Drug Design; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D066298:In Vitro Techniques; D013329:Structure-Activity Relationship; D014246:Trichomonas vaginalis / Q000187:drug effects; D014349:Trypanosoma cruzi / Q000187:drug effects
chemical_list: D000981:Antiprotozoal Agents; D001562:Benzimidazoles; D003497:Cyclic N-Oxides; D007093:Imidazoles; C487731:ethyl-1-(i-butyloxycarbonyloxy)-6-nitrobenzimid-azole-2-carboxylate