Regioselective cyclocondensations with thiobarbituric acid: spirocyclic and azocine products, X-ray characterization, and antioxidant evaluation

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dc.contributor.authorPolo-Cuadrado, Efraín
dc.contributor.authorAcosta-Quiroga, Karen
dc.contributor.authorRojas-Peña, Cristian
dc.contributor.authorRodriguez-Nuñez, Yeray A
dc.contributor.authorBlanco-Acuña, Edgard Fabián
dc.contributor.authorLopez, Jhon J.
dc.contributor.authorBrito, Iván
dc.contributor.authorCisterna, Jonathan
dc.contributor.authorAlderete, Joel B.
dc.contributor.authorGutiérrez, Margarita
dc.date.accessioned2025-04-04T21:21:08Z
dc.date.available2025-04-04T21:21:08Z
dc.date.issued0025-03
dc.descriptionINDEXACION SCOPUS
dc.description.abstractMulticomponent cyclocondensations of 5-amino-3-methyl-1-phenyl-1H-pyrazole (AMPZ), thiobarbituric acid, and p-formaldehyde under conventional thermal heating or ultrasonic irradiation were studied. Treatment of the reaction mixture in ethanol in an ultrasonic bath for 3 h produced azocine compound 4b, while the same mixture in ethanol under reflux conditions for 15 h produced spiro compound 4a. This work encompasses intricate experimental details, X-ray diffraction measurements, and multifaceted computational analyses employing methods such as the density functional theory and Hirshfeld surface analysis. Crystallographic investigations revealed the molecular structure of the compound and clarified its interactions involving hydrogen bonds and weak intermolecular forces. This article describes the synthesis and characterization of a novel spirocyclic compound. The study also evaluated the antioxidant potential in vitro using the DPPH and ABTS methods. The results showed that these compounds showed the best free radical scavenging ability, even in very small amounts, and that even at very low concentrations, these compounds showed excellent radical scavenging potential. Surprisingly, these compounds exhibited strong (ABTS+) radical scavenging activities, mainly attributed to the HAT mechanism, indicating their potential as therapeutic agents. Facile multipurpose, three-component selective procedures for new spiroheterocycles have been proposed, presenting intriguing perspectives in the field of medicine, particularly in the field of antioxidants. The geometric values of the computationally optimized structure were calculated using the density functional theory in LC-BLYP/6-31(d), aligned with the X-ray diffraction data, reinforcing the precision of our findings. © 2025 The Royal Society of Chemistry
dc.identifier.doi10.1039/d4ra07966c
dc.identifier.issn20462069
dc.identifier.urihttps://repositorio.unab.cl/handle/ria/63981
dc.language.isoen
dc.publisherRoyal Society of Chemistry
dc.subjectFree radical reactions; Hydrogen bonds; Regioselectivity; Ultrasonic applications; X ray diffraction analysis
dc.titleRegioselective cyclocondensations with thiobarbituric acid: spirocyclic and azocine products, X-ray characterization, and antioxidant evaluation
dc.typeArtículo
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Regioselective-cyclocondensations-with-thiobarbituric-acid-spirocyclic-and-azocine-products-Xray-characterization-and-antioxidant-evaluationRSC-Advances.pdf
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