Crystal structure, Hirshfeld surface analysis, and molecular dynamics simulations of two isostructural N-propargyl-4-(2-oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinolines
Autor
Güiza, Fausto M.
Rodríguez Núñez, Yeray A.
Ramírez, David
Romero Bohórquez, Arnold R.
Henao, José Antonio
Toro, Robert A.
Delgado, Jose Miguel
Diaz de Delgado, Graciela
Resumen
Two 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.
Colecciones
Ítems relacionados
Mostrando ítems relacionados por Título, autor o materia.
-
Article
Synthesis, biological evaluation, and molecular simulation of chalcones and aurones as selective MAO-B inhibitors (2020)
Morales-Camilo N.; Salas C.O.; Sanhueza C.; Espinosa-Bustos C.; Sepúlveda-Boza S.; Reyes-Parada M.; Gonzalez-Nilo F.; Caroli-Rezende M.; Fierro A. (Blackwell Publishing Ltd, 2015) -
Article
Multi-target-directed ligands for Alzheimer's disease: Discovery of chromone-based monoamine oxidase/cholinesterase inhibitors (2020)
Reis J.; Cagide F.; Valencia M.E.; Teixeira J.; Bagetta D.; Pérez C.; Uriarte E.; Oliveira P.J.; Ortuso F.; Alcaro S.; ... (Elsevier Masson SAS, 2018) -
Article
Synthesis and structure-activity relationship study of novel 3-heteroarylcoumarins based on pyridazine scaffold as selective MAO-B inhibitors (2020)
Costas-Lago M.C.; Besada P.; Rodríguez-Enríquez F.; Viña D.; Vilar S.; Uriarte E.; Borges F.; Terán C. (Elsevier Masson SAS, 2017)