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Molecules 2016, 21(6), 707; doi:10.3390/molecules21060707

Synthesis and Characterization of New 3-(4-Arylpiperazin-1-yl)-2-hydroxypropyl 4-Propoxybenzoates and Their Hydrochloride Salts

1
Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1, 61242 Brno, Czech Republic
2
Zentiva k.s., U kabelovny 130, 10237 Prague 10, Czech Republic
3
Institute of Macromolecular Chemistry, Academy of Sciences of the Czech Republic, Heyrovsky sq. 2, 16206 Prague 6, Czech Republic
4
CEITEC—Central European Institute of Technology, Masaryk University, Kamenice 753/5, 62500 Brno, Czech Republic
5
Global Change Research Institute CAS, Belidla 986/4a, 60300 Brno, Czech Republic
6
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojarov 10, 83232 Bratislava, Slovakia
*
Authors to whom correspondence should be addressed.
Academic Editor: Richard A. Bunce
Received: 12 April 2016 / Revised: 16 May 2016 / Accepted: 23 May 2016 / Published: 1 June 2016
(This article belongs to the Collection Heterocyclic Compounds)
View Full-Text   |   Download PDF [3406 KB, uploaded 1 June 2016]   |  

Abstract

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 13C-CP/MAS and 15N-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. View Full-Text
Keywords: arylcarbonyloxyaminopropanols; phenylpiperazines; synthesis; CP/MAS NMR spectroscopy; IR spectroscopy; principle components analysis arylcarbonyloxyaminopropanols; phenylpiperazines; synthesis; CP/MAS NMR spectroscopy; IR spectroscopy; principle components analysis
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MDPI and ACS Style

Marvanova, P.; Padrtova, T.; Pekarek, T.; Brus, J.; Czernek, J.; Mokry, P.; Humpa, O.; Oravec, M.; Jampilek, J. Synthesis and Characterization of New 3-(4-Arylpiperazin-1-yl)-2-hydroxypropyl 4-Propoxybenzoates and Their Hydrochloride Salts. Molecules 2016, 21, 707.

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