Expanding the chemical space of aryloxy-naphthoquinones as potential anti-Chagasic agents: synthesis and trypanosomicidal activity

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dc.contributor.authorBecerra, Nohemi A.
dc.contributor.authorEspinosa Bustos, Christian
dc.contributor.authorVazquez, Karina
dc.contributor.authorRivera, Gildardo
dc.contributor.authorPaulino, Margot
dc.contributor.authorCantero, Jorge
dc.contributor.authorNogueda, Benjamin
dc.contributor.authorChacon Vargas, Fabiola
dc.contributor.authorCastillo Velazquez, Uziel
dc.contributor.authorElizondo Rodriguez, Ana F.
dc.contributor.authorToledo, Sofia
dc.contributor.authorMoreno Rodriguez, Adriana
dc.contributor.authorAranda, Mario
dc.contributor.authorSalas, Cristian O.
dc.date.accessioned2024-01-10T14:23:06Z
dc.date.available2024-01-10T14:23:06Z
dc.date.issued2021
dc.description.abstractIn continuation our effort to research the chemical space of aryloxy-naphthoquinones as potential anti-Chagas agents, we synthesized nine derivatives and these compounds were evaluated in vitro against the epimastigote and trypomastigote forms of Mexican strains of Trypanosoma cruzi (T. cruzi). Most of these derivatives are highly active against epimastigote forms (IC50 < 1.0 mu M) compared to the reference drug benznidazole (Bzn). Then these were evaluated on trypomastigotes, which is showing better potency results than Bzn for compounds 3b and 3g. In addition, the cytotoxicity of these compounds was determined on the murine macrophage cell line J774. 3b and 3i were the most selective compounds against NINOA trypomastigote and INC-5 epimastigote forms, respectively. Further these compounds also have good oral bioavailability according to theoretical predictions. Finally, we were able to determine optimal substitution patterns using pharmacophoric models. All these results are provided very useful structural information to continue our designing of naphthoquinone derivatives against T. cruzi.
dc.description.abstract[GRAPHICS]
dc.description.funderFONDECYT
dc.description.funderDIPOG
dc.fechaingreso.objetodigital2024-03-21
dc.format.extent10 páginas
dc.fuente.origenWOS
dc.identifier.doi10.1007/s00044-021-02809-3
dc.identifier.eissn1554-8120
dc.identifier.issn1054-2523
dc.identifier.urihttps://doi.org/10.1007/s00044-021-02809-3
dc.identifier.urihttps://repositorio.uc.cl/handle/11534/80044
dc.identifier.wosidWOS:000710058300001
dc.information.autorucFacultad de Química y de Farmacia; Aranda Bustos, Mario Antonio; S/I; 1103178
dc.language.isoen
dc.nota.accesocontenido parcial
dc.publisherSPRINGER BIRKHAUSER
dc.revistaMEDICINAL CHEMISTRY RESEARCH
dc.rightsacceso restringido
dc.subjectTrypanosoma cruzi
dc.subjectTrypomastigote
dc.subjectEpimastigote
dc.subjectAryloxy-naphthoquinones
dc.subjectPharmacophoric analysis
dc.subjectADME properties
dc.subjectDRUG CANDIDATES
dc.subjectBENZNIDAZOLE
dc.subjectDERIVATIVES
dc.subject.ods03 Good Health and Well-being
dc.subject.odspa03 Salud y bienestar
dc.titleExpanding the chemical space of aryloxy-naphthoquinones as potential anti-Chagasic agents: synthesis and trypanosomicidal activity
dc.typeartículo
sipa.codpersvinculados1103178
sipa.indexWOS
sipa.trazabilidadCarga SIPA;09-01-2024
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