Three-Component Access to Functionalized Spiropyrrolidine Heterocyclic Scaffolds and Their Cholinesterase Inhibitory Activity (2020)

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[1] : Département de Chimie, Faculté des Sciences de Monastir
[2] : Universiti Sains Malaysia
[3] : Institut UTINAM (UMR 6213) (Université de Franche-Comté)
[4] : Observatoire des Sciences de l'Univers - Terre, Homme, Environnement, Temps, Astronomie (UAR 3245) (Université de Franche-Comté)
[5] : Technische Universität Dortmund
Description :
A novel one-pot [3+2]-cycloaddition reaction of (E)-3-arylidene-1-phenyl-succinimides, cyclic 1,2-diketones (isatin, 5-chloro-isatin and acenaphtenequinone), and diverse α-aminoacids such as 2-phenylglycine or sarcosine is reported. The reaction provides succinimide-substituted dispiropyrrolidine derivatives with high regio- and diastereoselectivities under mild reaction conditions. The stereochemistry of these N-heterocycles has been confirmed by four X-ray diffraction studies. Several synthetized compounds show higher inhibition on acetylcholinesterase (AChE) than butyrylcholinesterase (BChE). Of the 17 synthesized compounds tested, five exhibit good AChE inhibition with IC50 of 11.42 to 22.21 µM. A molecular docking study has also been undertaken for compound 4n possessing the most potent AChE inhibitory activity, disclosing its binding to the peripheral anionic site of AChE enzymes.
Discipline :
chemistry, organic (chemistry)

General metadata

Data acquisition date : from 2019 to 2020
Data acquisition methods :
Update periodicity : no update
Language : English (eng)
Formats : application/pdf
Audience : Research
Publications :
  • Three-Component Access to Functionalized Spiropyrrolidine Heterocyclic Scaffolds and Their Cholinesterase Inhibitory Activity (doi:10.3390/molecules25081963)
Record created 12 Mar 2021 by Michael Knorr.
Local identifier: FR-18008901306731-2021-03-12.

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Université de Bourgogne, Université de Franche-Comté, UTBM, AgroSup Dijon, ENSMM, BSB, Arts des Metiers