Synthesis and Characterization of New 3-(4-Arylpiperazin-1-yl)-2-hydroxypropyl 4-Propoxybenzoates and Their Hydrochloride Salts.
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.
Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1, 61242 Brno, Czech Republic. marvanovap@gmail.com.
Pavlina
P
Marvanova
Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1, 61242 Brno, Czech Republic. padrtova.tereza@seznam.cz.
Tereza
T
Padrtova
Zentiva k.s., U kabelovny 130, 10237 Prague 10, Czech Republic. tomas.pekarek@atlas.cz.
Tomas
T
Pekarek
Institute of Macromolecular Chemistry, Academy of Sciences of the Czech Republic, Heyrovsky sq. 2, 16206 Prague 6, Czech Republic. brusjiri@seznam.cz.
Jiri
J
Brus
Institute of Macromolecular Chemistry, Academy of Sciences of the Czech Republic, Heyrovsky sq. 2, 16206 Prague 6, Czech Republic. czernek@imc.cas.cz.
Jiri
J
Czernek
Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1, 61242 Brno, Czech Republic. mokryp@vfu.cz.
Petr
P
Mokry
CEITEC-Central European Institute of Technology, Masaryk University, Kamenice 753/5, 62500 Brno, Czech Republic. otakar.humpa@ceitec.muni.cz.
Otakar
O
Humpa
Global Change Research Institute CAS, Belidla 986/4a, 60300 Brno, Czech Republic. oravec.m@czechglobe.cz.
Michal
M
Oravec
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojarov 10, 83232 Bratislava, Slovakia. josef.jampilek@gmail.com.
Josef
J
Jampilek
D000959:Antihypertensive Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001565:Benzoates / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D000077489:Piperazine; D010879:Piperazines / Q000737:chemistry*; D012492:Salts / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared
D000959:Antihypertensive Agents; D001565:Benzoates; D010879:Piperazines; D012492:Salts; D000077489:Piperazine
CP/MAS NMR spectroscopy; IR spectroscopy; arylcarbonyloxyaminopropanols; phenylpiperazines; principle components analysis; synthesis