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

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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. Royal Society of Chemistry. doi:10.25666/DATAOSU-2019-03-21-02

General metadata

Identifier : 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

Administrative metadata

Data creatorsAffiliation
Anthony PesquetULHN (FRA)
Hamid MarzagULHN (FRA)
Michael KnorrUTINAM (FRA)
Carsten StrohmannTU Dortmund (DEU)
Ata Martin LawsonULHN (FRA)
Alina GhinetLIRIC (FRA)
Joëlle DuboisICSN (FRA)
Amaury FarceLIRIC (FRA)
Adam DaïchULHN (FRA)
Mohamed OthmanULHN (FRA)
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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