Application of aziridinium ring opening for preparation of optically active diamine and triamine analogues: Highly efficient synthesis and evaluation of DTPA-based MRI contrast enhancement agents.

Autor: Sun X; Department of Chemistry, Illinois Institute of Technology, Chicago, IL, USA., Chen Y; Department of Chemistry, Illinois Institute of Technology, Chicago, IL, USA., Wu N; Department of Chemistry, Illinois Institute of Technology, Chicago, IL, USA., Kang CS; Department of Chemistry, Illinois Institute of Technology, Chicago, IL, USA., Song HA; Department of Chemistry, Illinois Institute of Technology, Chicago, IL, USA., Jin S; Department of Chemistry, Illinois Institute of Technology, Chicago, IL, USA., Fu Y; Department of Chemistry, Illinois Institute of Technology, Chicago, IL, USA., Bryant H Jr; Laboratory of Diagnostic Radiology Research, Clinical Center, National Institutes of Health, Bethesda, Maryland, USA., Frank JA; Laboratory of Diagnostic Radiology Research, Clinical Center, National Institutes of Health, Bethesda, Maryland, USA., Chong HS; Department of Chemistry, Illinois Institute of Technology, Chicago, IL, USA.
Jazyk: angličtina
Zdroj: RSC advances [RSC Adv] 2015 Jan 01; Vol. 5 (115), pp. 94571-94581. Date of Electronic Publication: 2015 Nov 03.
DOI: 10.1039/C5RA11306G
Abstrakt: Ring opening of aziridinium ions with nitrogen nucleophiles was applied to the highly efficient synthesis of optically active vicinal diamines and diethylene triamine pentaacetic acid (DTPA) analogues as potential magnetic resonance imaging (MRI) contrast enhancement agents. The synthetic method features a column-free isolation of the regiospecific and stereospecific nucleophilic substitution products of enantiomerically enriched aziridinium ions in excellent yield.
Databáze: MEDLINE