Three-Component Access to Functionalized Spiropyrrolidine Heterocyclic Scaffolds and Their Cholinesterase Inhibitory Activity (2020)
Data creators :
Sarra Boudriga [1],
Saoussen Haddad [1],
Vikneswaran Murugaiyah [2],
Mohedinne Askri [1],
Michael Knorr [3] [4],
Carsten Strohmann [5],
Christopher Golz [5]
[1] : Département de Chimie, Faculté des Sciences de Monastir
[2] : Universiti Sains Malaysia
[3] : Institut UTINAM (Université Marie et Louis Pasteur)
[4] : Observatoire des Sciences de l'Univers - Terre, Homme, Environnement, Temps, Astronomie (Université Marie et Louis Pasteur)
[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 :
- Experimental data : Organic synthesis
Crystal structure
Modelling
Biological activity - Simulation or computational data : Docking studies
Formats :
application/pdf
Audience :
Research
Publications :
- Three-Component Access to Functionalized Spiropyrrolidine Heterocyclic Scaffolds and Their Cholinesterase Inhibitory Activity (doi:10.3390/molecules25081963)
Publisher :
Multidisciplinary Digital Publishing Institute
DOI and links
10.25666/DATAOSU-2021-03-12
https://dx.doi.org/doi:10.25666/DATAOSU-2021-03-12
https://search-data.ubfc.fr/FR-18008901306731-2021-03-12
Quotation
Sarra Boudriga, Saoussen Haddad, Vikneswaran Murugaiyah, Mohedinne Askri, Michael Knorr, Carsten Strohmann, Christopher Golz (2020): Three-Component Access to Functionalized Spiropyrrolidine Heterocyclic Scaffolds and Their Cholinesterase Inhibitory Activity . MDPI. doi:10.25666/DATAOSU-2021-03-12
Record created 12 Mar 2021 by Michael Knorr.
Local identifier: FR-18008901306731-2021-03-12.
