Phenoxy- and Phenylamino-Heterocyclic Quinones: Synthesis and Preliminary Anti-Pancreatic Cancer Activity

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dc.contributor.authorSanchez, Patricio
dc.contributor.authorSalas, Cristian O.
dc.contributor.authorGallardo-Fuentes, Sebastian
dc.contributor.authorVillegas, Alondra
dc.contributor.authorVeloso, Nicolas
dc.contributor.authorHonores, Jessica
dc.contributor.authorInman, Martyn
dc.contributor.authorIsaacs, Mauricio
dc.contributor.authorContreras, Renato
dc.contributor.authorMoody, Christopher J.
dc.contributor.authorCisterna, Jonathan
dc.contributor.authorBrito, Ivan
dc.contributor.authorTapia, Ricardo A.
dc.date.accessioned2024-01-10T12:37:11Z
dc.date.available2024-01-10T12:37:11Z
dc.date.issued2022
dc.description.abstractThe successful application of fragment-based drug discovery strategy for the efficient synthesis of phenoxy- or phenylamino-2-phenyl-benzofuran, -benzoxazole and -benzothiazole quinones is described. Interestingly, in the final step of the synthesis of the target compounds, unusual results were observed on the regiochemistry of the reaction of bromoquinones with phenol and aniline. A theoretical study was carried out for better understanding the factors that control the regiochemistry of these reactions. The substituted heterocyclic quinones were evaluated in vitro to determine their cytotoxicity by the MTT method in three pancreatic cancer cell lines (MIA-PaCa-2, BxPC-3, and AsPC-1). Phenoxy benzothiazole quinone 26a showed potent cytotoxic activity against BxPC-3 cell lines, while phenylamino benzoxazole quinone 20 was the most potent on MIA-PaCa-2 cells. Finally, electrochemical properties of these quinones were determined to correlate with a potential mechanism of action. All these results, indicate that the phenoxy quinone fragment led to compounds with increased activity against pancreatic cancer cells.
dc.fechaingreso.objetodigital04-04-2024
dc.fuente.origenWOS
dc.identifier.doi10.1002/cbdv.202101036
dc.identifier.eissn1612-1880
dc.identifier.issn1612-1872
dc.identifier.urihttps://doi.org/10.1002/cbdv.202101036
dc.identifier.urihttps://repositorio.uc.cl/handle/11534/76778
dc.identifier.wosidWOS:000796760600001
dc.information.autorucFacultad de Química y de Farmacia; Honores Sotelo, Jessica Scarlet; S/I; 217991
dc.issue.numero6
dc.language.isoen
dc.nota.accesoContenido parcial
dc.publisherWILEY-V C H VERLAG GMBH
dc.rightsacceso restringido
dc.subjectheterocycles
dc.subjectquinones
dc.subjecttheoretical study
dc.subjectantitumor agents
dc.subjectcyclic voltammetry
dc.subject.ods03 Good Health and Well-being
dc.subject.odspa03 Salud y bienestar
dc.titlePhenoxy- and Phenylamino-Heterocyclic Quinones: Synthesis and Preliminary Anti-Pancreatic Cancer Activity
dc.typeartículo
dc.volumen19
sipa.codpersvinculados217991
sipa.indexWOS
sipa.trazabilidadCarga SIPA;09-01-2024
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