Synthesis of new compounds of the aryloxyaminopropanol type and their HPLC enantioseparation

[1] Aboul-Enein HY, Ali I. HPLC enantiomeric resolution of nebivolol on normal and reversed amylose based chiral phases. Pharmazie. 2001;56:214-216.Search in Google Scholar

[2] Agrawal YK, Patel RN. Chiral chromatographic separation of β-blockers. J Chromatogr B. 2005;820:23-31.10.1016/j.jchromb.2005.03.003Search in Google Scholar

[3] Bojarsky J. Stereoselective chromatography of cardiovascular drugs: an update. J Biochem Biophys Methods. 2002;54:197-220.10.1016/S0165-022X(02)00143-4Search in Google Scholar

[4] Bojarsky J, Aboul - Enein YH, Ghanem A. What/s new in chromatographic enantioseparations. Curr Anal Chem. 2005;1:59-77.10.2174/1573411052948433Search in Google Scholar

[5] Bruchata K, Čižmarikova R. New derivatives of aryloxyaminopropanol- structure biological activity relationship. (Review in Slovak). Farm Obzor. 2010;79:287-293.Search in Google Scholar

[6] Čižmarikova R, Dingova A, Kozlovsky J, Greksakova O.Derivatives of para-hydroxyacetophenones and parahydroxypropiophenones as novel potential beta-adrenolytic agent (in Slovak). Čes Slov Farm. 1990a;39:403-408.Search in Google Scholar

[7] Čižmarikova R, Mlynarčik D, Greksakova O, Račanska E: Unspezifische Wirkungen der Derivate des p-Hydroxypropiophenones - potentielle Beta-Adrenolytika.Pharmazie. 1990b;45:142-143.Search in Google Scholar

[8] Čižmarikova R, Kozlovsky J. Anticalcium effect of 4-hydroxypropiophenone derivatives-potential blockers of beta-adrenoceptors (in Slovak). Čes Slov Farm. 1994a;3:226-228.Search in Google Scholar

[9] Čižmarikova R, Kozlovsky J. Pharmacological evaluation of 4-hydroxypropiophenone-potential beta-adrenoreceptor blockers (in Slovak). Farm Obzor. 1994b;63:258-260.Search in Google Scholar

[10] Čižmarikova R, Račanska E. Beta-adrenergic receptor blockers II. Aryloxyaminopropanols. (Review in Slovak).Farm Obzor. 1998;67:113-117.Search in Google Scholar

[11] Čižmarikova R, Polakovičova M, Mišikova E. Synthesis, physicochemical properties and conformational studies of (3-chloromethyl-4-hydroxyphenyl)ethanones. Chem Papers. 2002;56:256-260.Search in Google Scholar

[12] Čižmarikova R, Račanska E, Hroboňova K, Lehotay J, Mišikova E. Synthesis and enantioseparation od some aryloxyaminopropanol derivatives and their effect on the central nervous system. Acta Facult Pharm Univ Comenianae. 2003;50:38-50.Search in Google Scholar

[13] Čižmarikova R, Nemethy A, Valentova J, Hroboňova K, Bruchata K. Synthesis and HPLC enantioseparation of derivatives of the 3-hydroxyphenylethanone. Acta Facult Pharm Univ Comenianae. 2012;50:38-50.10.2478/v10219-012-0023-7Search in Google Scholar

[14] Fornstedt T, Gotmar G, Andersson M, Guiochon G: Dependence on the mobile phase pH of the adsorption behavior of propranolol enantiomers on a cellulase protein used as the chiral selector. J Am Chem Soc. 1999;121:1164-1174.10.1021/ja9831296Search in Google Scholar

[15] Fulde K, Frahm AW: Temperature-induced inversion of elution order in the enantioseparation of sotalol on a cellobiohydrolase I-based stationary phase. J Chromatogr A. 1999;858:33-43.10.1016/S0021-9673(99)00798-0Search in Google Scholar

[16] Griffith R.K. Adrenergics and adrenergic blocking agents.In Abraham, D.J. Burger/s Medicinal Chemistry and Drug Discovery. Vol.6. Nervous system agents 6th ed New York: John Wiley sons, INC. 2003; p. 1-39.10.1002/0471266949.bmc093Search in Google Scholar

[17] Hroboňova K, Lehotay J, Čižmarikova R, Armstrong DW.Study of mechanism of enantioseparation. Part I. Chiral analysis of alkylaminoderivatives of aryloxypropanols by HPLC using macrocyclic antibiotics as chiral selectors. J Liq Chromatogr Rel Technol. 2001;24:2225-2237.10.1081/JLC-100105136Search in Google Scholar

[18] Hroboňova K, Lehotay J, Čižmarikova R. HPLC enantioseparation of potential β-blockers of the aryloxyaminopropanol type. Pharmazie. 2004;59:828-832.Search in Google Scholar

[19] Kečkešova S, Sedlarova E. Review of the ultrashort-acting beta-adrenergic blockers. (Review in Slovak). Farm Obzor. 2010;79:3-13.Search in Google Scholar

[20] Mosti L, Menozzi G, Fossa P et al. Synthesis and preliminary biological evaluation of novel N-substituted 1-amino-3-[1-methyl(phenyl)-1H-indazol-4-yloxy] propan-2-ols interesting as potential antiarrhytmic, local anaesthetic and analgesic agent. Arzneim Forsch / Drug Res. 2000;50:963-972.Search in Google Scholar

[21] 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. Chromatographia. 2003;11/12:733-740.Search in Google Scholar

[22] Wang Z, Ouyang J, Baeyens WRG. Recent development of enantioseparation techniques for adrenergic drugs using liquid chromatography and capillary electrophoresis.A review. J Chromatogr B. 2008;862:1-14.10.1016/j.jchromb.2007.11.03418164252Search in Google Scholar

[23] Wang X, Ching BCH. Liquid chromatographic retention behavior and enantiomeric separation of three chiral center β-blocker Drug (Nadolol) using heptakis(6-azido-6-deoxy-2,3-di-O-phenylcarbamolted) β-cyclodextrin.Bonded chiral stationary phase. Chirality. 2002:14:798-805.10.1002/chir.1014112395397Search in Google Scholar

[24] 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: 653-658.10.1365/s10337-008-0747-7Search in Google Scholar