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

Čižmáriková R. 1 , Némethy A. 1 , Valentová J. 1 , Hroboňová K. 2 , and Adamcová K. 1
  • 1 Comenius University in Bratislava, Faculty of Pharmacy, Department of Chemical Theory of Drugs, Bratislava, Slovak Republic
  • 2 Slovak University of Technology, Faculty of Chemical and Food Technology, Institute of Analytical Chemistry, Bratislava, Slovak Republic

Abstract

This article describes a preparation of some new compounds of the aryloxyaminopropanol type derived from 4-hydroxyphenylpropan- 1-one with phenylamino, cyclohexylamino and isobutylamino group in the hydrophilic part and methoxymethyl or ethoxymethyl substituent in the lipophilic part of the molecule. The purity of the prepared compounds was checked by thinlayer chromatography and the structure was confirmed on the basis of interpretation of the IR, UV, 1H NMR and 13C NMR spectra. An enantioseparation of the prepared compounds was performed by using high-performance liquid chromatography on an amylase tris(3,5-dimethylphenylcarbamate) (Chiralpak AD) and native teicoplanin (Chirobiotic T). The chromatographic results such as retention, separation and resolution factors have shown that Chiralpak AD is more suitable for enantioseparation of some of the prepared compounds.

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