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

• Authors: Jan Tengler , Iva Kapustíková , Ondřej Stropnický , Petr Mokrý , Michal Oravec , Jozef Csöllei , Josef Jampílek
• Languages of publication: EN

Abstracts

EN

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. [...]

Keywords

EN

Aryloxyaminopropanol; Beta-blockers; Acid dissociation constant; 1H NMR spectroscopy; Ultrashort effect

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2013
• Volume: 11
• Issue: 11
• Pages: 1757-1767

Dates

published

1 - 11 - 2013

online

25 - 8 - 2013

Contributors

author

Jan Tengler

author

Iva Kapustíková

• Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical sciences Brno, 612 42, Brno, Czech Republic

author

Ondřej Stropnický

• Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical sciences Brno, 612 42, Brno, Czech Republic

author

Petr Mokrý

• Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical sciences Brno, 612 42, Brno, Czech Republic

author

Michal Oravec

• Global Change Research Centre AS CR, 603 00, Brno, Czech Republic

author

Jozef Csöllei

• Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical sciences Brno, 612 42, Brno, Czech Republic

author

Josef Jampílek

• Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical sciences Brno, 612 42, Brno, Czech Republic

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Identifiers

DOI

10.2478/s11532-013-0302-8