3-spiroindolizines containing an isoindole ring through intra-molecular arylation of spiro-N-acyliminium species (2019)

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[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.
Disciplines :
chemistry, organic (chemistry), biochemistry & molecular biology (fundamental biology)

General metadata

Data acquisition date : from Jan 2017 to Oct 2018
Data acquisition methods :
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)
Record created 21 Mar 2019 by Michael Knorr.
Local identifier: FR-18008901306731-2019-03-21-02.

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