Schuster, Andreas and Götte, Carsten and Bernhardt, Günther and Buschauer, Armin (2001) Chiral separation of pheniramine-like 3-phenyl-3-heteroarylpropylamines by CE and HPLC methods,. Chirality 13 (6), pp. 285-293.
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Analytical CE and HPLC methods were developed for the chiral separation of halogen-substituted 3-phenyl-3-(2-pyridyl)propylamines 1-4 (1: 3-(4-fluorophenyl), 2: 3-(3,4-difluorophenyl), 3: 3-(4-chlorophenyl), 4: 3-(3,4-dichlorophenyl)), 3-(4-fluorophenyl)-3-(2-thiazolyl)propylamine (5), and 3-(4-fluorophenyl)-3-(1-benzylimidazol-2-yl)propylamine (6), which are building blocks for the preparation of very potent arpromidine-type histamine H2 receptor agonists. All amines were enantioseparated by CE with resolutions of at least 1.8 using -, -, or -cyclodextrin (CD) as chiral selectors. With heparin as buffer additive for CE the optical antipodes of 1-4 and 6 were separated with resolutions 1.8. On RP-18 columns the separation of the (+)-(S)-acetylmandelic acid amides of racemic 2 (R = 0.9, = 1.07) and the thioureas prepared by addition of 6 to 2,3,4,6-tetra-O-acetyl--D-glucopyranosyl isothiocyanate (R = 2.0, = 1.20) was successful, whereas the diastereomeric ureas prepared from 3 and (+)-(S)-1-(1-naphthyl)ethyl isocyanate could not be resolved. Separation of the diastereomeric isoindoles prepared from 1-5, o-phthaldialdehyde and 2,3,4,6-tetra-O-acetyl-1-thio--D-glucopyranoside was achieved on a RP-18 phase (R 0.4, a 1.02). Direct separation of the enantiomers of 3 and 4 was achieved on a Cyclobond I column (R 0.9, 1.07). - and -CD were also useful as mobile phase additives for HPLC (3 and 4: RP-18 column, -CD, R 0.4, 1.03; 3: RP-18 column, -CD: R = 0.5, = 1.04). Chirality 13:285-293, 2001.
|Institutions:||Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical/Medicinal Chemistry II (Prof. Buschauer)|
|Keywords:||cyclodextrins; heparin; diastereomeric derivatives; (+)-(s)-acetylmandelic acid; 2,3,4,6-tetra-O-acetyl--D-glucopyranosyl isothiocyanate; 2,3,4,6-tetra-O-acetyl-1-thio--D-glucopyranoside; o-phthaldialdehyde; cyclobond|
|Subjects:||500 Science > 570 Life sciences|
600 Technology > 610 Medical sciences Medicine
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Yes|
|Owner:||Prof. Armin Buschauer|
|Deposited On:||22 Feb 2008 07:45|
|Last Modified:||05 Aug 2009 13:42|