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.
Highlights
Antagonists of β-adrenergic receptors, so-called β-blockers, are essential drugs that have been widely used in the treatment of many cardiovascular and non-cardiovascular diseases for more than 50 years
Tosylate and physical datasubstances were in agreement with reported in the literature was necessary intermediate 1 was prepared according to the published procedure, and the spectroscopic andto maintain the temperature at 0 C to obtain good yields
Raising the temperature or prolonging the the literature but wasthe prepared by reaction a different syntheticIntermediate method, and thealready spectroscopic data was in reaction lowered yield of the dramatically
Summary
Antagonists of β-adrenergic receptors, so-called β-blockers, are essential drugs that have been widely used in the treatment of many cardiovascular and non-cardiovascular diseases for more than 50 years. E.g., ester moiety) is incorporated into the structure of approved drugs, and in the spot they as hydrochloride salts to increase their solubility in water. The position of protonation of (β-adrenolytic activity; the ester moiety ensures ultra-short effect) and the phenylpiperazine nitrogen atoms in the piperazine ring of hydrochloride salts was determined by means of 13CCP/MAS and 15N-CP/MAS. The arylcarbonyloxyaminopropanol scaffoldactivity is formed the discussed compounds is provided by theacid) presence of the at arylcarbonyloxyaminopropanol the benzene ring (as a part of 4-hydroxybenzoic substituted the C(4) position with a propoxy esterpart moiety ultra-short effect) and the or chain.pharmacophore. The phenylpiperazine segment, the basic part of the molecule, is either the biological effects of the discussed salts of 3-(4-arylpiperazin-1-yl)-2-hydroxypropyl unsubstituted or substituted with a methoxy or a fluoro moiety in the C(2)′ or C(4)′ position. As determined well as investigational structural features [2]; the biological effects of the discussed salts of 3-(4-arylpiperazin-
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