Structural analysis of some bis-(8-isopropyl-isoquinolinium) derivatives reveals a preferential folded conformation leading to a stereoselective attack by sodium borohydride
[en] Reduction of symmetrical bis-isoquinolinium derivatives with sodium borohydride generates
normally a mixture of three 1,2,3,4-tetrahydroisoquinoline stereoisomers. In a series of 8-
isopropyl analogues, chiral resolution failed for the analogues with propyl and m-xylyl linkers
since two and one peaks respectively were detected by HPLC. Further analysis by MS and
CD of both peaks of the propyl analogue revealed that each peak corresponds to an
enantiomer. Conformational analysis and X-ray cristallography showed a folded conformation
of the propyl and m-xylyl analogues responsible for the observed stereoselectivity following
the reduction step. Additional 1H NMR investigations confirm structural features detected by
theoretical analysis.
Research center :
Centre Interfacultaire de Recherche du Médicament - CIRM Giga-Neurosciences - ULiège
Hubert, Philippe ; Université de Liège - ULiège > Département de pharmacie > Chimie analytique
Seutin, Vincent ; Université de Liège - ULiège > Département des sciences biomédicales et précliniques > Pharmacologie
Wouters, Johan; Université de Namur > Département de Chimie
Liégeois, Jean-François ; Université de Liège - ULiège > Département de pharmacie > Chimie pharmaceutique
Language :
English
Title :
Structural analysis of some bis-(8-isopropyl-isoquinolinium) derivatives reveals a preferential folded conformation leading to a stereoselective attack by sodium borohydride
Publication date :
June 2014
Journal title :
Journal of Molecular Structure
ISSN :
0022-2860
eISSN :
1872-8014
Publisher :
Elsevier Science, Amsterdam, Netherlands
Peer reviewed :
Peer Reviewed verified by ORBi
Name of the research project :
SK Channels
Funders :
F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE] SPW DGO6 PPP NEUREDGE Collective grant of the University of Liège Research grant from Wallonie Bruxelles International
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