Cargando…

Selenoxide Elimination Triggers Enamine Hydrolysis to Primary and Secondary Amines: A Combined Experimental and Theoretical Investigation

We discuss a novel selenium-based reaction mechanism consisting in a selenoxide elimination-triggered enamine hydrolysis. This one-pot model reaction was studied for a set of substrates. Under oxidative conditions, we observed and characterized the formation of primary and secondary amines as elimin...

Descripción completa

Detalles Bibliográficos
Autores principales:	Ribaudo, Giovanni, Bortoli, Marco, Oselladore, Erika, Ongaro, Alberto, Gianoncelli, Alessandra, Zagotto, Giuseppe, Orian, Laura
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	MDPI 2021
Materias:	Article
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8125833/ https://www.ncbi.nlm.nih.gov/pubmed/34066723 http://dx.doi.org/10.3390/molecules26092770

Ejemplares similares

Fluoxetine scaffold to design tandem molecular antioxidants and green catalysts
por: Ribaudo, Giovanni, et al.
Publicado: (2020)

Synthesis and Evaluation of Bithiazole Derivatives As Potential α-Sarcoglycan Correctors
por: Ribaudo, Giovanni, et al.
Publicado: (2023)

Combining Electrospray Mass Spectrometry (ESI-MS) and Computational Techniques in the Assessment of G-Quadruplex Ligands: A Hybrid Approach to Optimize Hit Discovery
por: Ribaudo, Giovanni, et al.
Publicado: (2021)

Insight into the LFA-1/SARS-CoV-2 Orf7a Complex by Protein–Protein Docking, Molecular Dynamics, and MM-GBSA Calculations
por: Ongaro, Alberto, et al.
Publicado: (2021)

Therapeutic Potential of Phosphodiesterase Inhibitors against Neurodegeneration: The Perspective of the Medicinal Chemist
por: Ribaudo, Giovanni, et al.
Publicado: (2020)

ROS-Scavenging Selenofluoxetine Derivatives Inhibit In Vivo Serotonin Reuptake
por: Ribaudo, Giovanni, et al.
Publicado: (2022)

Antioxidant Potential of Psychotropic Drugs: From Clinical Evidence to In Vitro and In Vivo Assessment and toward a New Challenge for in Silico Molecular Design
por: Ribaudo, Giovanni, et al.
Publicado: (2020)

Effect of the enamine pyramidalization direction on the reactivity of secondary amine organocatalysts
por: Schnitzer, Tobias, et al.
Publicado: (2020)

The Key Role of Chalcogenurane Intermediates in the Reduction Mechanism of Sulfoxides and Selenoxides by Thiols Explored In Silico
por: Madabeni, Andrea, et al.
Publicado: (2023)

Theoretical Studies of [2,3]-Sigmatropic Rearrangements of Allylic Selenoxides and Selenimides
por: Bayse, Craig A., et al.
Publicado: (2009)

Dynamic Covalent Chemistry of Aldehyde Enamines: Bi(III)‐ and Sc(III)‐Catalysis of Amine–Enamine Exchange
por: Zhang, Yang, et al.
Publicado: (2017)

Antioxidant Chimeric Molecules: Are Chemical Motifs Additive? The Case of a Selenium-Based Ligand
por: Zeppilli, Davide, et al.
Publicado: (2023)

Psychiatric Disorders and Oxidative Injury: Antioxidant Effects of Zolpidem Therapy disclosed In Silico
por: Bortoli, Marco, et al.
Publicado: (2019)

Selenoxides as Excellent Chalcogen Bond Donors: Effect of Metal Coordination
por: Burguera, Sergi, et al.
Publicado: (2022)

Bond Energies of Enamines
por: Li, Yao, et al.
Publicado: (2022)

Virtual Screening-Accelerated Discovery of a Phosphodiesterase 9 Inhibitor with Neuroprotective Effects in the Kainate Toxicity In Vitro Model
por: Landucci, Elisa, et al.
Publicado: (2023)

An Updated Overview on the Role of Small Molecules and Natural Compounds in the “Young Science” of Rejuvenation
por: Ribaudo, Giovanni, et al.
Publicado: (2023)

A water-soluble selenoxide reagent as a useful probe for the reactivity and folding of polythiol peptides()
por: Arai, Kenta, et al.
Publicado: (2012)

Hydrogenation of unactivated enamines to tertiary amines: rhodium complexes of fluorinated phosphines give marked improvements in catalytic activity
por: Tin, Sergey, et al.
Publicado: (2015)

Catalytic oxidant scavenging by selenium-containing compounds: Reduction of selenoxides and N-chloramines by thiols and redox enzymes
por: Carroll, Luke, et al.
Publicado: (2017)

Three Component Cascade Reaction of Cyclohexanones, Aryl Amines, and Benzoylmethylene Malonates: Cooperative Enamine-Brønsted Acid Approach to Tetrahydroindoles
por: Cortes Vazquez, Jose, et al.
Publicado: (2022)

A Perspective on Natural and Nature-Inspired Small Molecules Targeting Phosphodiesterase 9 (PDE9): Chances and Challenges against Neurodegeneration
por: Ribaudo, Giovanni, et al.
Publicado: (2021)

Drug Design: Where We Are and Future Prospects
por: Zagotto, Giuseppe, et al.
Publicado: (2021)

The Bright Side of Psychedelics: Latest Advances and Challenges in Neuropharmacology
por: Mastinu, Andrea, et al.
Publicado: (2023)

Radical Scavenging Potential of Ginkgolides and Bilobalide: Insight from Molecular Modeling
por: Zeppilli, Davide, et al.
Publicado: (2023)

Iminium and enamine catalysis in enantioselective photochemical reactions
por: Zou, You-Quan, et al.
Publicado: (2018)

Configurational and Constitutional Dynamics of Enamine Molecular Switches
por: Ren, Yansong, et al.
Publicado: (2020)

Combined experimental and theoretical studies of regio- and stereoselectivity in reactions of β-isoxazolyl- and β-imidazolyl enamines with nitrile oxides
por: Efimov, Ilya V, et al.
Publicado: (2016)

Synthesis and antibacterial activities of enamine derivatives of dehydroacetic acid
por: Baldwin, Alex G., et al.
Publicado: (2017)

Investigation of biphenyl enamines for applications as p-type semiconductors
por: Steponaitis, Matas, et al.
Publicado: (2023)

Counterion-Enhanced Pd/Enamine Catalysis: Direct Asymmetric α-Allylation of Aldehydes with Allylic Alcohols by Chiral Amines and Achiral or Racemic Phosphoric Acids
por: Pálvölgyi, Ádám Márk, et al.
Publicado: (2020)

Copper(II)-Mediated Synthesis of Indolequinones from Bromoquinones and Enamines
por: Inman, Martyn, et al.
Publicado: (2013)

Differentiation between enamines and tautomerizable imines in the oxidation reaction with TEMPO
por: Jie, Xiaoming, et al.
Publicado: (2018)

Alkyne Aminopalladation/Heck and Suzuki Cascades: An Approach to Tetrasubstituted Enamines
por: Geffers, Finn J., et al.
Publicado: (2021)

An Overlooked Pathway in 1,3‐Dipolar Cycloadditions of Diazoalkanes with Enamines
por: Li, Le, et al.
Publicado: (2022)

C- and N-Phosphorylated Enamines—An Avenue to Heterocycles: NMR Spectroscopy
por: Larina, Lyudmila
Publicado: (2023)

Cannabidiol preferentially binds TRPV2: a novel mechanism of action
por: Landucci, Elisa, et al.
Publicado: (2022)

From a Molecule to a Drug: Chemical Features Enhancing Pharmacological Potential
por: Ribaudo, Giovanni, et al.
Publicado: (2022)

Mechanism of the Stereoselective α-Alkylation of Aldehydes Driven by the Photochemical Activity of Enamines
por: Bahamonde, Ana, et al.
Publicado: (2016)

The effect of S-alkylation on organocatalytic enamine activation through imidazolidine-4-thiones
por: Hensinger, Magenta J., et al.
Publicado: (2023)

Cannot write session to /tmp/vufind_sessions/sess_p0oj77vah11gtj30oa8v5kuckq