Synthesis of new (arylcarbonyloxy) aminopropanol derivatives and the determination of their physico-chemical properties

0396558 - ÚVGZ 2014 RIV PL eng J - Článek v odborném periodiku
Tengler, J. - Kapustíková, I. - Stropnický, O. - Morký, P. - Oravec, Michal - Csoellei, J. - Jampílek, J.
Synthesis of new (arylcarbonyloxy) aminopropanol derivatives and the determination of their physico-chemical properties.
Central European Journal of Chemistry. Roč. 11, č. 11 (2013), s. 1757-1767. ISSN 1895-1066
Grant CEP: GA MŠMT(CZ) ED1.1.00/02.0073
Institucionální podpora: RVO:67179843
Klíčová slova: Aryloxyaminopropanol * Beta-blockers * Acid dissociation constant * 1H NMR spectroscopy * Ultrashort effect
Kód oboru RIV: EH - Ekologie - společenstva
Impakt faktor: 1.329, rok: 2013

Eight hydrochlorides of 3-{2-[(2/4-fluorophenoxy)-ethylamino]}-2-hydroxypropyl-4-alkoxybenzoates and four hydrochlorides of 3-tert-butylamino-2-hydroxypropyl-4-butoxybenzoates were prepared as potential antagonists of the β1-adrenergic receptor (beta-blockers). A multistep synthesis of these compounds is described as well as their detailed analytical characterization. The pharmacokinetic properties of these weak base compounds are significantly influenced by their acid-base dissociation constant, pK a. The knowledge of this value is crucial for new drug development. This paper is aimed at developing a methodology that utilizes pH-dependent 1H NMR spectroscopy for its routine analysis. The selected predicted physico-chemical parameters of the new (arylcarbonyloxy)aminopropanols (i.e., aryloxyaminopropanol derivatives) were compared with the model drugs esmolol and flestolol.
Trvalý link: http://hdl.handle.net/11104/0224313