Synthesis and characterization of new 3-(4-arylpiperazin-1-yl)-2-hydroxypropyl 4-propoxybenzoates and their hydrochloride salts

0459919 - ÚMCH 2017 RIV CH eng J - Journal Article
Marvanova, P. - Padrtova, T. - Pekárek, T. - Brus, Jiří - Czernek, Jiří - Mokrý, P. - Humpa, O. - Oravec, Michal - Jampílek, J.
Synthesis and characterization of new 3-(4-arylpiperazin-1-yl)-2-hydroxypropyl 4-propoxybenzoates and their hydrochloride salts.
Molecules. Roč. 21, č. 6 (2016), 707_1-707_13. E-ISSN 1420-3049
R&D Projects: GA ČR(CZ) GA14-03636S; GA MŠMT(CZ) LO1415; GA MŠMT(CZ) LM2015061
Institutional support: RVO:61389013 ; RVO:67179843
Keywords : arylcarbonyloxyaminopropanols * phenylpiperazines * synthesis
OECD category: Polymer science; Environmental sciences (social aspects to be 5.7) (UEK-B)
Impact factor: 2.861, year: 2016

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.
Permanent Link: http://hdl.handle.net/11104/0260123