Dataset : 3-spiroindolizines containing an isoindole ring through intra-molecular arylation of spiro-N-acyliminium species

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General metadata

Identifiers :
local : FR-18008901306731-2019-03-21-02 external : doi:10.25666/DATAOSU-2019-03-21-02 , doi:10.1039/c8ob02612b
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)
Keywords :

Dates :
Data acquisition : from Jan 2017 to Oct 2018
Data provision : 7 Feb 2019
Metadata record : Creation : 21 Mar 2019

Language : English (eng)
Audience : Research
RightsAttribution, No Derivs
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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

Administrative metadata

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)
Publisher : Royal Society of Chemistry
Science contact : Michael Knorr website e-mail
Access : available

Technical metadata

Formats : application/pdf, chemical/x-cif
Data acquisition methods :
Datatype : Dataset

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)

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