Furanyl chalcone derivatives as efficient singlet oxygen quenchers. An experimental and DFT/MRCI study

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dc.contributor.authorDiaz Uribe, Carlos
dc.contributor.authorVallejo, William
dc.contributor.authorFlorez, Jiress
dc.contributor.authorTrilleras, Jorge
dc.contributor.authorGutierrez, Margarita
dc.contributor.authorRodriguez Serrano, Angela
dc.contributor.authorSchott, Eduardo
dc.contributor.authorZarate, Ximena
dc.date.accessioned2024-01-10T13:48:39Z
dc.date.available2024-01-10T13:48:39Z
dc.date.issued2020
dc.description.abstractThis study reports the antioxidant activity against singlet oxygen (O-1(2)) of five newly synthesized furanyl chalcones (FCs) (E)-3 (5-(4 chlorophenyl)furan-2-yl)-1-arylprop-2-en-1-ones (3a-e). Their structural difference is based on the aryl substituent as follows (Ar): 3a = -C6H4-OCH3, 3b = -C6H3-(1,2-OCH3), 3c = -C6H4OC6H4, 3d = - C10H6-(OCH3) and 3e = -C4H3O. We used a Claisen-Schmidt condensation involving a 5-(4-chlorophenyl)furan-2-carbaldehyde and the corresponding ketones under ultrasonic irradiation. Their property to O-1(2) quenching was analyzed in terms of the rate constant for the process (k(Q) at 25 degrees C) determined by the Stern-Volmer model in ethanol. For the compounds 3c, 3d and 3e, the k(Q) values are slightly larger respect to 3a and 3b. The FCs 3c behaves as the best quencher (k(Q )of 8.44 (+/- 0.09) x 10(7) M-1 s(-1)). Geometry analysis and electronic structure calculations have been performed in the framework of Density Functional Theory (DFT) and DFT/Multi-Reference Configuration Interaction (DFT/MRCI) methods. According to DFT/MRCI, a physical quenching of O-1(2) from the ground states of the FCs may not likely induce a spontaneous energy transfer processes but a chemical quenching mechanism may dominate the kinetics. (C) 2020 Elsevier Ltd. All rights reserved.
dc.description.funderFONDECYT
dc.description.funderPIEI QUIMBIO, UTALCA
dc.description.funderMillennium Science Initiative of the Ministry of Economy, Development and Tourism-Chile grant Nuclei on Catalytic Processes towards Sustainable Chemistry (CSC)
dc.fechaingreso.objetodigital11-04-2024
dc.format.extent8 páginas
dc.fuente.origenWOS
dc.identifier.doi10.1016/j.tet.2020.131248
dc.identifier.issn0040-4020
dc.identifier.urihttps://doi.org/10.1016/j.tet.2020.131248
dc.identifier.urihttps://repositorio.uc.cl/handle/11534/79385
dc.identifier.wosidWOS:000537423800005
dc.information.autorucQuímica;Schott Verdugo Eduardo Enrique;S/I;1020229
dc.issue.numero24
dc.language.isoen
dc.nota.accesoContenido parcial
dc.publisherPERGAMON-ELSEVIER SCIENCE LTD
dc.revistaTETRAHEDRON
dc.rightsacceso restringido
dc.subjectSinglet oxygen quenching
dc.subjectFuranyl chalcones
dc.subjectDFT/MRCI
dc.subjectSUBSTITUTED CHALCONES
dc.subjectBIOLOGICAL EVALUATION
dc.subjectELECTRON-TRANSFER
dc.subjectFLAVONOIDS
dc.subjectANTIOXIDANT
dc.subjectAURONES
dc.subjectDESIGN
dc.subjectDAMAGE
dc.subject.ods03 Good Health and Well-being
dc.subject.odspa03 Salud y bienestar
dc.titleFuranyl chalcone derivatives as efficient singlet oxygen quenchers. An experimental and DFT/MRCI study
dc.typeartículo
dc.volumen76
sipa.codpersvinculados1020229
sipa.indexWOS
sipa.indexScopus
sipa.trazabilidadCarga SIPA;09-01-2024
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