title: In vitro antiparasitic activity of new thiosemicarbazones in strains of Trypanosoma cruzi.
abstract: In this study thiosemicarbazones derivatives of 5-[(trifluoromethyl)phenylthio]-2-furaldehyde were synthesized and evaluated in terms of their efficiency in challenging the growth of epimastigote forms of Trypanosoma cruzi, the etiological agent of Chagas' disease. A number of compounds were synthesized from 5-bromo-2-furfuraldehyde using nucleophilic aromatic substitution, with a series of trifluoromethyl thiolates, followed by condensation reactions with thiosemicarbazide. Their molecular structures were determined by (1)H, (13)C and (19)F NMR, MS and IR spectroscopy. When tested with T. cruzi, they showed a stronger reaction, similar to nifurtimox and benznidazole, with the 5-[nitro-4-(trifluoromethyl)phenyltio]-2-furaldehyde thiosemicarbazone (compound 4) showing the highest antiparasitic activity. This improved activity may be explained due to the nitro group present in the molecule, which potentiates its activity. The thiosemicarbazone derivatives in this study showed no apoptosis in platelets or monocytes, nor did they induce platelet activation. The trypanocidal activity of these substances represents a good starting point for a medicinal chemistry program aimed at therapy for Chagas' disease.
authors.affiliation: Facultad de Ciencias Químicas, Área de Inorgánica, UABJO, Oaxaca 68120, Mexico; Unidad de Bioquímica e Inmunología, ITO-UNAM, Oaxaca 68030, Mexico.
authors.forename: Adriana
authors.initials: A
authors.lastname: Moreno-Rodríguez
authors.affiliation: Facultad de Medicina, Departamento de Microbiología y Parasitología, UNAM, México DF 04510, Mexico.
authors.forename: Paz María
authors.initials: PM
authors.lastname: Salazar-Schettino
authors.affiliation: Facultad de Ciencias Químicas, Área de Inorgánica, UABJO, Oaxaca 68120, Mexico.
authors.forename: Juan Luis
authors.initials: JL
authors.lastname: Bautista
authors.affiliation: Facultad de Química, UNAM, México DF 04510, Mexico.
authors.forename: Francisco
authors.initials: F
authors.lastname: Hernández-Luis
authors.affiliation: Facultad de Química, UNAM, México DF 04510, Mexico.
authors.forename: Hugo
authors.initials: H
authors.lastname: Torrens
authors.affiliation: Facultad de Medicina, Departamento de Microbiología y Parasitología, UNAM, México DF 04510, Mexico.
authors.forename: Yolanda
authors.initials: Y
authors.lastname: Guevara-Gómez
authors.affiliation: Centro de Investigación Facultad de Medicina UNAM-UABJO, Oaxaca CP68020, Mexico.
authors.forename: Socorro
authors.initials: S
authors.lastname: Pina-Canseco
authors.affiliation: Facultad de Medicina, Departamento de Microbiología y Parasitología, UNAM, México DF 04510, Mexico.
authors.forename: Martha Bucio
authors.initials: MB
authors.lastname: Torres
authors.affiliation: Facultad de Medicina, Departamento de Microbiología y Parasitología, UNAM, México DF 04510, Mexico.
authors.forename: Margarita
authors.initials: M
authors.lastname: Cabrera-Bravo
authors.affiliation: Facultad de Química, UNAM, México DF 04510, Mexico.
authors.forename: Cesar Mendoza
authors.initials: CM
authors.lastname: Martinez
authors.affiliation: Unidad de Bioquímica e Inmunología, ITO-UNAM, Oaxaca 68030, Mexico; Centro de Investigación Facultad de Medicina UNAM-UABJO, Oaxaca CP68020, Mexico. Electronic address: perezcampos@prodigy.net.mx.
authors.forename: Eduardo
authors.initials: E
authors.lastname: Pérez-Campos
mesh_terms: D017209:Apoptosis / Q000187:drug effects; D001792:Blood Platelets / Q000187:drug effects* / Q000469:parasitology; D002478:Cells, Cultured; D014355:Chagas Disease / Q000188:drug therapy*; D005434:Flow Cytometry; D006801:Humans; D066298:In Vitro Techniques; D015394:Molecular Structure; D009000:Monocytes / Q000187:drug effects* / Q000469:parasitology; D015539:Platelet Activation / Q000187:drug effects*; D013882:Thiosemicarbazones / Q000737:chemistry*; D014344:Trypanocidal Agents / Q000737:chemistry / Q000494:pharmacology*; D014349:Trypanosoma cruzi / Q000187:drug effects*
chemical_list: D013882:Thiosemicarbazones; D014344:Trypanocidal Agents
keywords: Apoptosis; Platelet activation; Structure–activity relationship; Thiosemicarbazones; Trypanocidal activity