Novel antiprotozoal products: imidazole and benzimidazole N-oxide derivatives and related compounds.
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.
Aguirre
Gabriela
G
Departamento de Química Orgánica, Facultad de Química-Facultad de Ciencias, Montevideo, Uruguay.
Boiani
Mariana
M
Cerecetto
Hugo
H
Gerpe
Alejandra
A
González
Mercedes
M
Sainz
Yolanda Fernández
YF
Denicola
Ana
A
De Ocáriz
Carmen Ochoa
CO
Nogal
Juan José
JJ
Montero
David
D
Escario
José Antonio
JA
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
D000981:Antiprotozoal Agents; D001562:Benzimidazoles; D003497:Cyclic N-Oxides; D007093:Imidazoles; C487731:ethyl-1-(i-butyloxycarbonyloxy)-6-nitrobenzimid-azole-2-carboxylate