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. RSC. doi:10.1039/c8ob02612b

General metadata

Identifier : local : FR-18008901306731-2019-03-21-02 external : 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
Hamid MarzagULHN
Michael KnorrUTINAM
Carsten StrohmannTU Dortmund
Ata Martin LawsonULHN
Alina GhinetLIRIC
Joëlle DuboisICSN
Amaury FarceLIRIC
Adam DaïchULHN
Mohamed OthmanULHN
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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