Schuster, Andreas and Goette, Carsten and Bernhardt, Guenther and Buschauer, Armin (2001) Chiral separation of pheniramine-like 3-phenyl-3-heteroarylpropylamines by CE and HPLC methods. CHIRALITY, 13 (6). pp. 285-293. ISSN 0899-0042
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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 H-2 receptor agonists. All amines were enantioseparated by CE with resolutions of at least 1.8 using alpha-, beta-, or gamma -cyclodextrin (CD) as chiral selectors. With heparin as buffer additive for CE the optical antipodes of 1-4 and 6 were separated with resolutions greater than or equal to1.8. On RP-18 columns the separation of the (+)-(S)-acetylmandelic acid amides of racemic 2 (R = 0.9, alpha = 1.07) and the thioureas prepared by addition of 6 to 2,3,4, 6-tetra-O-acetyl-beta -D-glucopyranosyl isothiocyanate (R = 2.0, alpha = 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-0-acetyl-1-thio-beta -D-glucopyranoside was achieved on a RP-18 phase (R greater than or equal to 0.4, a greater than or equal to 1.02). Direct separation of the enantiomers of 3 and 4 was achieved on a Cyclobond I column (R greater than or equal to 0.9, alpha 1.07). alpha- and beta -CD were also useful as mobile phase additives for HPLC (3 and 4: RP-18 column, beta -CD, R greater than or equal to 0.4, alpha greater than or equal to 1.03; 3: RP-18 column, (alpha -CD: R = 0.5, alpha =1.04). Chirality 13:285-293, 2001. (C) 2001 Wiley-Liss, Inc.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PERFORMANCE LIQUID-CHROMATOGRAPHY; CAPILLARY-ZONE-ELECTROPHORESIS; H-2-RECEPTOR AGONISTS; BETA-CYCLODEXTRIN; MOBILE-PHASE; STEREOISOMERS; ARPROMIDINE; ENANTIOMERS; RESOLUTION; ACID; cyclodextrins; heparin; diastereomeric derivatives; (+)-(s)-acetylmandelic acid; 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate; 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-glucopyranoside; o-phthaldialdehyde; cyclobond I |
| Subjects: | 600 Technology > 615 Pharmacy |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy > Alumni or Retired Professors > Pharmaceutical/Medicinal Chemistry II (Prof. Buschauer) |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 28 Feb 2022 07:26 |
| Last Modified: | 28 Feb 2022 07:26 |
| URI: | https://pred.uni-regensburg.de/id/eprint/41841 |
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