Mostrar el registro sencillo del ítem

dc.contributor.authorGüiza, Fausto M.
dc.contributor.authorRodríguez Núñez, Yeray A.
dc.contributor.authorRamírez, David
dc.contributor.authorRomero Bohórquez, Arnold R.
dc.contributor.authorHenao, José Antonio
dc.contributor.authorToro, Robert A.
dc.contributor.authorDelgado, Jose Miguel
dc.contributor.authorDiaz de Delgado, Graciela
dc.date.accessioned2022-01-25T16:56:28Z
dc.date.available2022-01-25T16:56:28Z
dc.date.issued2022-04-15
dc.identifier10.1016/j.molstruc.2021.132280
dc.identifier.issn00222860
dc.identifier.urihttps://hdl.handle.net/20.500.12728/9893
dc.description.abstractTwo new N-propargyl-4-(2-oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinoline derivatives (4a and 4b), have been efficiently prepared through a one-pot InCl3-catalyzed cationic Povarov reaction between N-propargylanilines (1a and 1b), formaldehyde (2) and N-vinyl-pyrrolidin-2-one (3). These compounds were characterized by ATR-FTIR spectroscopy, 1H/13C NMR spectroscopy, ESI-IT mass spectrometry, and by single-crystal X-ray diffraction. N-propargyl-6-methyl-4-(2′-oxopyrrolidin-1′-yl)-1,2,3,4-tetrahydroquinoline (4a) and N-propargyl-6-chloro-4-(2′-oxopyrrolidin-1′-yl)-1,2,3,4-tetrahydroquinoline (4b) are isostructural and crystallize in space group P21/c. The crystal structures are characterized by inversion-related interpenetrated helices along the b-axis that form columns along the c-axis. C—H···O, C—H···C, and C—H···π(aryl) for 4a and C—H···O, C—H···Cl, and C—H···π(aryl) for 4b interactions occur within the columns which are connected by C—H···π(propargyl) interactions. These features were further visualized by Hirshfeld surface analysis and energy frameworks calculations and evaluated by the EXY enrichment ratio. Molecular dynamics simulations show that these compounds are promising monoamine oxidase B (MAO‐B) inhibitors, since they interact with MAO-B in a similar manner as rasagiline, a drug commonly used in the treatment of Parkinson's and Alzheimer's diseases.es_ES
dc.language.isoenes_ES
dc.publisherElsevier B.V.es_ES
dc.subjectCationic Povarov reactiones_ES
dc.subjectCrystal structurees_ES
dc.subjectMolecular dynamics simulationses_ES
dc.subjectMonoamine oxidase B inhibitorses_ES
dc.subjectN-propargylamineses_ES
dc.subjectTetrahydroquinolinees_ES
dc.titleCrystal structure, Hirshfeld surface analysis, and molecular dynamics simulations of two isostructural N-propargyl-4-(2-oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinolineses_ES
dc.typeArticlees_ES


Ficheros en el ítem

Thumbnail

Este ítem aparece en la(s) siguiente(s) colección(ones)

Mostrar el registro sencillo del ítem