JOURNAL OF THE CZECH PHARMACEUTICAL SOCIETY AND THE SLOVAK PHARMACEUTICAL SOCIETY

Čes. slov. farm. 2011, 60(3):137-143

Synthesis and basic physicochemical properties of 1-[3-(Y-alkoxyphenylcarbamoyloxy)-2--hydroxypropyl]-4-(2-methylphenyl)piperazinium chlorides

Ivan Malík1,*, Eva Sedlárová1, Fils Andriamainty1, Jana Gališinová1, Jozef Csöllei2, Ján Vančo2
1 Univerzita Komenského Bratislava, Farmaceutická fakulta, Katedra farmaceutickej chémie
2 Veterinární a farmaceutická univerzita Brno, Farmaceutická fakulta, Ústav chemických léčiv

1-[3-(Y-Alkoxyphenylcarbamoyloxy)-2-hydroxypropyl]-4-(2-methylphenyl)piperazinium chlorides (labelled as

7a-7d) were prepared within a complex study of the relationships between the chemical structure, physicochemical properties and biological (antiarrhythmic, antihypertensive) activity of dual acting compounds. Chemical structures of basic forms (labelled as

7a2C-7d2C) and appropriate monochlorides (labelled as

7a-7d) were confirmed by 1H-NMR, 13C-NMR, MS and IR spectral and elemental analysis. The estimated physicochemical parameters included the melting point data, solubility profile in various media, purity checking (adsorption thin-layer chromatography), surface activity determination (Traube stalagmometric method), acidobasic characteristics (pKa value determination by alkalimetric titration) as well as the log ε values estimation by UV/VIS spectrophotometry. Other experimental values under consideration were lipohydrophilic characteristics using reversed-phase thin-layer chromatography (RM readouts) RP-HPLC (log k' data) and the log Pexps estimated in octan-1-ol/phosphate buffer medium.

Keywords: dual acting α- and ß-blockers; N-phenylpiperazine; spectral characteristics; acidobasic properties; lipophilicity

Received: February 24, 2011; Accepted: March 30, 2011; Published: March 1, 2011  Show citation

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Malík I, Sedlárová E, Andriamainty F, Gališinová J, Csöllei J, Vančo J. Synthesis and basic physicochemical properties of 1-[3-(Y-alkoxyphenylcarbamoyloxy)-2--hydroxypropyl]-4-(2-methylphenyl)piperazinium chlorides. Čes. slov. farm. 2011;60(3):137-143.
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