Synthesis of new (arylcarbonyloxy)aminopropanol derivatives and the determination of their physico-chemical properties

Abstract

Abstract:

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

“…Raising the temperature or prolonging the reaction lowered the yield of the reaction dramatically. Intermediate 2 was already described in the literature but was prepared by a different synthetic method, and the spectroscopic data was in agreement with the literature [13]. In the first two steps of the synthesis, the commercially available 4-propoxybenzoic acid was transformed to the potassium salt by potassium hydroxide in a mixture of methanol and propan-2-ol in ratio 1:3.…”

“…In this regard, considering all possible sources of the signal broadening and splitting, we must take into account a possible presence of different enantiomers in the analysed systems. In principle, 13 C-CP/MAS NMR spectra of different enantiomers usually differ in terms of the positions and intensities of the corresponding resonance frequencies [16]. Consequently, if a racemic mixture is formed, the presence of "chiral" impurities can be reflected by the additional set of NMR signals.…”

“…Compounds were prepared as hydrochloride salts to increase their solubility in water. 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 spectroscopy and IR spectroscopy. The cardiovascular activity of the discussed compounds is provided by the presence of the arylcarbonyloxyaminopropanol pharmacophore (β-adrenolytic activity; the ester moiety ensures ultra-short effect) and the phenylpiperazine fragment (α 1 -adrenolytic activity) [2,8].…”

Chromatographic and Computational Study of Hydro-lipophilic Properties of <em>N</em>-Alkoxyphenylhydroxy-naphthalenecarboxamides

“…Since it was found that the lipophilicity of these significantly biologically effective agents determined their activity, in this study hydrolipophilic properties of all three series are investigated. Thus this contribution is a follow-up work to the previous papers [5][6][7][8][15][16][17][18][19][20][21][22][23][24][25] aimed at the physicochemical properties of new biologically active agents.…”

“…Therefore, reversed-phase high performance liquid chromatography (RP-HPLC) methods have become popular and widely used for lipophilicity measurement. A general procedure is the measurement of directly accessible retention time under isocratic conditions with varying amounts of an organic modifier in the mobile phase using end-capped non-polar C 18 stationary RP columns and calculating the capacity factor k [4][5][6][7][8]. Log k, calculated from the capacity factor k, is used as the lipophilicity index converted to log P scale [4].…”