Nine new dihydrochloride salts of 3-(4-arylpiperazin-1-yl)-2-hydroxypropyl 4-alkoxyethoxybenzoates were designed and synthesized. The physicochemical properties such as lipophilicity index (log kw) and dissociation constant (pKa) were experimentally determined and compared to the software calculated data. The lipophilicity index was determined by means of reversed-phase high performance liquid chromatography (RP-HPLC). The pKa values were determined by means of capillary zone electrophoresis. The "drug-likeness" properties according to the Lipinski Rule of Five and prediction of possible blood-brain barrier penetration were computed and discussed.

• Klíčová slova
• Lipinski rules, arylcarbonyloxyaminopropanols, blood–brain barrier, lipophilicity index, pKa determination, phenylpiperazines,
• MeSH
• benzoáty chemická syntéza   chemie   MeSH
• chemické jevy MeSH
• chromatografie s reverzní fází metody   MeSH
• hydrofobní a hydrofilní interakce MeSH
• koncentrace vodíkových iontů MeSH
• lipidy chemie   MeSH
• software * MeSH
• vysokoúčinná kapalinová chromatografie metody   MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• benzoáty MeSH
• lipidy MeSH

Five new 3-(4-arylpiperazin-1-yl)-2-hydroxypropyl 4-propoxybenzoates were designed and synthesized as potential dual antihypertensive agents. The compounds were prepared as free bases and subsequently transformed to hydrochloride salts. The position of protonation of nitrogen atoms in the piperazine ring of hydrochloride salts was determined by means of (13)C-CP/MAS and (15)N-CP/MAS NMR and IR spectroscopy. Using these solid-state analytical techniques, it was found that both nitrogen atoms were protonated when excess hydrogen chloride was used for preparation of salts. On the other hand, when the equimolar amount of hydrogen chloride was used, piperazine nitrogen substituted by aryl was protonated.

• Klíčová slova
• CP/MAS NMR spectroscopy, IR spectroscopy, arylcarbonyloxyaminopropanols, phenylpiperazines, principle components analysis, synthesis,
• MeSH
• antihypertenziva chemická syntéza   chemie   MeSH
• benzoáty chemická syntéza   chemie   MeSH
• magnetická rezonanční spektroskopie MeSH
• molekulární konformace MeSH
• molekulární modely MeSH
• piperazin MeSH
• piperaziny chemie   MeSH
• soli chemie   MeSH
• spektroskopie infračervená s Fourierovou transformací MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• antihypertenziva MeSH
• benzoáty MeSH
• piperazin MeSH
• piperaziny MeSH
• soli MeSH