Reversed-Phase Liquid Chromatographic Separation, on Cellulose Chiral Stationary Phases, of the Stereoisomers of Methoxytetra-hydronaphthalene Derivatives, New Agonist and Antagonist Ligands for Melatonin Receptors
作者： E. Lipka , C. Descamps , C. Vaccher , J. P. Bonte
DOI: 10.1365/S10337-004-0491-6
关键词: Enantiomer 、 Agonist 、 Stereoselectivity 、 High-performance liquid chromatography 、 Carboxamide 、 Acetonitrile 、 Chemistry 、 Reversed-phase chromatography 、 Chromatography 、 Bicyclic molecule
摘要: A stereoselective high-performance liquid chromatographic method has been established for chiral separation of melatoninergic derivatives with one or two centers, new agonist and antagonist ligands melatonin receptors. Reversed-phase separations were performed on cellulose-based stationary phases—tris-3,5-dimethylphenylcarbamate (Chiralcel OD-RH) tris-methylbenzoate OJ-R). Water–modifier (methanol acetonitrile) mixtures in different proportions used as mobile phases. The effects organic mobile-phase modifier concentration, temperature, compound structure examined. Baseline (RS > 1.5) was readily obtained many the compounds.
springer.com
sci-hub.se 参考文章(27)
M.P. Vaccher, E. Lipka, C. Vaccher, J-P. Bonte, E. Fourmaintraux, Chiral Separation and Determination of the Enantiomeric Purity of Tetrahydronaphthalenic Derivatives, Melatoninergic Ligands, by HPLC using β–Cyclodextrins Chromatographia. ,vol. 58, pp. 665- 670 ,(2003) , 10.1365/S10337-003-0089-4
Klaas P Zuideveld, Nicoline Treijtel, Piet H Van der Graaf, Meindert Danhof, Enantioselective high-performance liquid chromatographic analysis of the 5-HT1A receptor agonist 8-hydroxy-2-(di-n-propylamino)tetralin. Application to a pharmacokinetic-pharmacodynamic study in rats. Journal of Chromatography B: Biomedical Sciences and Applications. ,vol. 738, pp. 67- 73 ,(2000) , 10.1016/S0378-4347(99)00493-4
Hassan Y. Aboul-Enein, Imran Ali, Gerald G�bitz, Claire Simons, Paul J. Nicholls, HPLC enantiomeric resolution of novel aromatase inhibitors on cellulose- and amylose-based chiral stationary phases under reversed phase mode Chirality. ,vol. 12, pp. 727- 733 ,(2000) , 10.1002/1520-636X(2000)12:10<727::AID-CHIR5>3.0.CO;2-T
Larry Miller, Cara Weyker, Effects of compound structure and temperature on the resolution of enantiomers of cyclopentenones by liquid chromatography on derivatized cellulose chiral stationary phases Journal of Chromatography A. ,vol. 653, pp. 219- 228 ,(1993) , 10.1016/0021-9673(93)83177-T
Sophie Durieux, Angéline Chanu, Christophe Bochu, Valérie Audinot, Sophie Coumailleau, Jean A. Boutin, Philippe Delagrange, Daniel H. Caignard, Caroline Bennejean, Pierre Renard, Daniel Lesieur, Pascal Berthelot, Saïd Yous, Design and synthesis of 3-phenyltetrahydronaphthalenic derivatives as new selective MT2 melatoninergic ligands. Part II. Bioorganic & Medicinal Chemistry. ,vol. 11, pp. 2963- 2974 ,(2003) , 10.1016/J.BMC.2009.03.023
T. O'Brien, L. Crocker, R. Thompson, K. Thompson, P. H. Toma, D. A. Conlon, B. Feibush, C. Moeder, G. Bicker, N. Grinberg, Mechanistic aspects of chiral discrimination on modified cellulose. Analytical Chemistry. ,vol. 69, pp. 1999- 2007 ,(1997) , 10.1021/AC961241L
Kozo Tachibana, Atsushi Ohnishi, Reversed-phase liquid chromatographic separation of enantiomers on polysaccharide type chiral stationary phases. Journal of Chromatography A. ,vol. 906, pp. 127- 154 ,(2001) , 10.1016/S0021-9673(00)00955-9
Abdelhalim Guelzim, Emmanuelle Belloli, Said Yous, Claude Vaccher, Absolute configuration of N-[(–)-2-(7-methoxy-1,2,3,4-tetrahydro-1-naphthyl)ethyl]cyclopropylcarboxamide, a highly potent and selective melatonin analogue Acta Crystallographica Section C-crystal Structure Communications. ,vol. 57, pp. 100- 101 ,(2001) , 10.1107/S0108270100014724
A. Ishikawa, T. Shffiata, Cellulosic Chiral Stationary Phase Under Reversed-Phase Condition Journal of Liquid Chromatography & Related Technologies. ,vol. 16, pp. 859- 878 ,(1993) , 10.1080/10826079308020939
J. G. Hou, Y. L. Wang, C. X. Li, X. Q. Han, J. Z. Gao, J. W. Kang, Reversed-phase separations on cellulose tris(3,5-dimethylphenylcarbamate) chiral stationary phase Chromatographia. ,vol. 50, pp. 89- 95 ,(1999) , 10.1007/BF02493623