Within the framework of the study of the synthesis and high-performance liquid chromatography (HPLC) enantioseparation the series of 9 derivatives of 3-hydroxyphenylethanone was prepared by a well-tried method. The structure of the prepared compounds was confirmed on the basis of interpretation of the IR, UV, 1H NMR and 13C NMR spectra. An enantioseparation of prepared compounds was performed using HPLC on a native teicoplanin (Chirobiotic T) and the amylose tris (3,5-dimethylphenylcarbamate) (Chiralpak AD) chiral stationary phases, which is more suitable for the enantioseparation of all prepared compounds especially with heterocycles in the basic part of a molecule.
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Abe I, Nishiyama T, Nakahara T, Frank H. Gas chromatographic enantiomer separation of pharmaceuticals on capillary columns coated with novel chiral polysiloxanes. J Chromatogr A. 1995;694:237-243.
Aboul-Enein HY, Bakr SA. Enantiomeric resolution of propranolol and analogs on two cellulose (Chiralcel of and OC) and one amylose (Chiralpak Ad) chiral stationary phases. J Liq Chrom Relat Tech. 1998;8:1137-1145.
Beck GM, Neau SH. Optimization of lambda-carrageenan as a chiral selector in capillary electrophoresis separations. Chirality. 2000;12:614-20.
Bhushan R, Arora M. Direct enantiomeric resolution of (±) atenolol, (±) metoprolol, and (±) propranolol by impregnated TLC using L-aspartic acid as chiral selector. Biomed Chrom. 2003;17:226-230.
Bhushan R, Tanwar S. Direct TLC resolution of atenolol and propranolol into their enantiomers using different chiral selectors as impregnating reagents. Biomed Chrom. 2008;22:1028-1034.
Bruchata K, Čižmarikova R, Polakovičova M, Hroboňova K, Pastirova Z. Synthesis, conformational study and HPLC enantioseparation of nitrophenoxyaminopropanols. Acta Facult Pharm Univ Comeniaenae. 2010;57:24-32.
Čižmarikova R, Bruchata K, Pastirova Z, Lehotay J, Hroboňova K. HPLC and TLC enantioseparation of the nitro-positioned aryloxysubstituted aminopropanols. Pharmazie. 2010;65:387-388.
Čižmarikova R, Račanska E, Hroboňova K, Lehotay J, Aghova Z, Halešova D. Synthesis, pharmacological activity and chromatographic separation of some novel potential β-blockers of the aryloxyaminopropanol type. Pharmazie. 2003;58:237-241.
Donnecke J, Paul C, Konig WA, Svensson LA, Gyllenhaal O, Vessman J. Immobilization of heptakis 6-O-terc-butyldimethylsilyl-2,3-O-methyl)-β-cyclodextrin for capillary gas chromatography and SFC and micro-liquid chromatography. J Microcolumn Sep. 1996;8:495-505.
Gyllenhaal O, Konig WA, Vessman J. Enantiomer separation of metoprolol and its analogues and metabolites by capillary column gas chromatography after derivatization with phosgene. J Chromatogr A. 1985;350:328-331.
Haginaka J, Okazaki Y, Matsunaga H. Separation of enantiomers on a chiral stationary phase based on ovoglycoprotein. V. Influence of immobilization method on chiral resolution. J Chromatogr A. 1999;840:171-181.
Henriksson H, Petterson G, Johansson G. Discrimination between enantioselective and non-selective binding sites on cellobiohydrolase-based stationary phases by site specific competing ligands. J Chromatogr A. 1999;857:107-115.
Hroboňova K, Lehotay J, Čižmarikova R. HPLC enantioseparation of potential β- blockers of the aryloxyaminopropanol type. Pharmazie. 2004;59:828-832.
Hroboňova K, Lehotay J, Čižmarikova R. HPLC separation of enantiomers of some potential β-blockers of the aryloxyaminopropanol type using macrocyclic antibiotic chiral stationary phases. Pharmazie. 2005;60:888-891.
Juvancz Z, Grolimund K, Schurig V. Pharmaceutical application of a bonded cyclodextrin stationary phase. J Microcolumn Sep. 1993;5:459-468.
Makamba H, Andrisano V, Gotti R, Cavrini V, Felix G. Sparteine as mobile phase modifier in the chiral separation of hydrophobic basic drugs on an α1-acid glycoprotein column. J Chromatogr A. 1998;818:43-52.
Matchett MW, Branch SK, Jefferies TM. Polar organic chiral separation of propranolol and analogues using a β-cyclodextrin bonded stationary phase. Chirality. 1996;8:126-130.
Park KL, Kim KH, Jung SH, Lim HM, Hong CH, Kang JS. Enantioselective stabilization of inclusion complexes of metoprolol in carboxymethylated β-cyclodextrin. J Pharmaceut Biomed Anal. 2000;27:569-576.
Petersen PV, Ekelund J, Olsen L, Ovesen SV. Chiral separations of β-blocking drug substances using Pirkle-type α-Burke 1 chiral stationary phase. J Chromatogr A. 1997;757:65-71.
Proksa B. Capillary zone electrophoretic separation of (R,S)-metipranolol and related substances. Pharmazie. 1999;54:431-434.
Proksa B, Čižmarikova R. Separation of β-adrenolytics derivated from 4- hydroxyacetophenone by capillary electrophoresis in the presence of cyclodextrins. Anal Chim Acta. 2001;434:75-79.
Rastogi SN, Anand N, Gupta PP, Sharma JN. Agents acting on the central nervous system. 19. (±)-1-(o- and m-Alkanoylphenoxy)-3-(N4-arylpiperazinyl)propan-2-ols as local anesthetics, hypotensives, and tranquilizers. J Med Chem. 1973;16:797-804.
Sharma SC, Evans MB, Evans SJ. The enantiomeric separation of metipranolol and desacetylmetipranolol on a cellulose tris-3,5-dimethylphenylcarbamate chiral stationary phase. J Pharm Biomed Anal. 1995;13:129-137.
Valentova J, Čižmarikova R, Bui TTT, Drake AF, Hutt AJ. Enantiomeric resolution of novel aryloxyaminopropanol derivatives with β-adrenoceptor antagonist activity on a derivatised amylose chiral stationary phase. Chromatographia. 2003;58:733-740.
Zhang H, Shao H, Youmei A, Zhang Z. Optimized conditions of enantioseparation of β- blockers by CZE using carboxymethyl β-cyclodextrin as chiral selector. Chromatographia. 2008;68:653-658.