[en] A new method for the synthesis of 15N-labeled chiral ß-diamines from a common precursor, either optically pure amino acids or anti-ß-amino alcohols, is reported. The two diastereomeric series of vicinal diamines are produced through the nucleophilic ring opening of activated chiral aziridines. 15N was introduced by means of [15N]-benzylamine, prepared from 15NH4Cl. The final compounds are highly valuable because [1H-15N] NMR is considered a powerful tool for studying the chemical properties of platinum-based complexes.
Disciplines :
Pharmacy, pharmacology & toxicology
Author, co-author :
Berger, Gilles
Gelbcke, Michel
Cauët, Emilie
Luhmer, Michel
Nève, Jean
Dufrasne, François ; Université de Mons > Faculté de Médecine et de Pharmacie > Service de Chimie thérapeutique et Pharmacognosie
Language :
English
Title :
25. Synthesis of 15N-labeled vicinal diamines through N-activated chiral aziridines: tools for the NMR study of platinum-based anticancer compounds.
Publication date :
06 February 2013
Journal title :
Tetrahedron Letters
ISSN :
0040-4039
Publisher :
Elsevier, United Kingdom
Volume :
54
Issue :
6
Pages :
545-548
Research unit :
M136 - Chimie thérapeutique et Pharmacognosie
Research institute :
R550 - Institut des Sciences et Technologies de la Santé