3-spiroindolizines containing an isoindole ring through intra-molecular arylation of spiro-N-acyliminium species (2019)
Data creators :
Anthony Pesquet [1],
Hamid Marzag [1],
Michael Knorr [2] [3],
Carsten Strohmann [4],
Ata Martin Lawson [1],
Alina Ghinet [5],
Joëlle Dubois [6],
Amaury Farce [5],
Adam Daïch [1],
Mohamed Othman [1]
[1] : Normandie Université - Université Le Havre
[2] : Institut UTINAM (UMR 6213) (Université de Franche-Comté)
[3] : Observatoire des Sciences de l'Univers - Terre, Homme, Environnement, Temps, Astronomie (UAR 3245) (Université de Franche-Comté)
[4] : Technische Universität Dortmund
[5] : Lille Inflammation Research International Center
[6] : Institut de Chimie des Substances Naturelles (UPR 2301)
Description :
Based on N-acyliminium species, efficient approaches to spirocyclic systems connected by two different carbon centers to the isoindole ring have been developed. The imide reduction and the tandem oxidative cleavage of olefin/formyl-amide equilibration were at first selected as the key steps for these strategies. The intramolecular α-amidoalkylation reaction was achieved through the arylation of α-acetoxy lactams or α-hydroxy lactams using, respectively, a Lewis acid or a Brønsted acid depending on the nature of N-acyliminium precursors. All compounds have been characterized by NMR spectroscopy in solution, furthermore the molecular structure of one of this spirocyclic compounds has been elucidated by a single-crystal X-ray diffraction study.
The biological activitiy of these N-heterocyclic compounds on human farnesyltransferase has been investigated.
The biological activitiy of these N-heterocyclic compounds on human farnesyltransferase has been investigated.
Disciplines :
General metadata
Data acquisition date :
from Jan 2017 to Oct 2018
Data acquisition methods :
- Experimental data : X-Ray diffraction
NMR spectroscopy
Language :
English (eng)
Formats :
application/pdf, chemical/x-cif
Audience :
Research
Publications :
- Access to 3-spiroindolizines containing an isoindole ring through intra-molecular arylation of spiro-N-acyliminium species: a new family of potent farnesyltransferase inhibitors (doi:10.1039/C8OB02612B)
Publisher :
Royal Society of Chemistry
DOI and links
10.25666/DATAOSU-2019-03-21-02
https://dx.doi.org/doi:10.25666/DATAOSU-2019-03-21-02
https://search-data.ubfc.fr/FR-18008901306731-2019-03-21-02
Quotation
Anthony Pesquet, Hamid Marzag, Michael Knorr, Carsten Strohmann, Ata Martin Lawson, Alina Ghinet, Joëlle Dubois, Amaury Farce, Adam Daïch, Mohamed Othman (2019): 3-spiroindolizines containing an isoindole ring through intra-molecular arylation of spiro-N-acyliminium species. RSC. doi:10.25666/DATAOSU-2019-03-21-02
Record created 21 Mar 2019 by Michael Knorr.
Local identifier: FR-18008901306731-2019-03-21-02.