Analytical profile of 1-[3-(3-propoxyphenylcarbamoyloxy)-2-hydroxypropyl]-4-(3-tri-fluoromethylphenyl)piperazinium chloride

Česká verzia

Authors: Ivan Malík
Authors place of work: Univerzita Komenského Bratislava, Farmaceutická fakulta, Katedra farmaceutickej chémie
Published in the journal: Čes. slov. Farm., 2011; 60, 283-289
Category: Original Articles

Summary

The purpose of the paper was the completing of the experimentally estimated physicochemical descriptors spectrum of 1-[3-(3-propoxyphenylcarbamoyloxy)-2-hydroxypropyl]-4-(3-trifluoromethylphenyl)piperazinium chloride (labelled as 8e), an effective, highly lipophilic compound against non-tuberculous M. kansasii My 235/80. The identity of the structure 8e was verified by ¹H- and ¹³C-NMR spectral data, IR spectrometry and by elemental analysis as well. The readout from mass spectrometry confirmed an existence of the molecular ion [M + H⁺]⁺. The purity of the evaluated compound 8e was checked by absorption thin-layer chromatography, the stability of its aqueous and methanolic solutions was investigated under UV/VIS light. The values of some physicochemical descriptors assigned to 8e, which had been previously published (pK_a, log P_exp), were correlated with the constants associated with some antimycobacterially active molecules which are commonly used in therapeutical practice (isoniazid, pyrazinanide, para-aminosalicylic acid, ethionamide, streptomycine). For the content determination of the molecule of 8e, RP-HPLC (reversed-phase HPLC) method with an internal standard and UV/VIS spectrophotometry at the wavelength of 238 nm (aqueous medium) and at 244 nm (methanolic medium) were used.

Key words:
non-tuberculous mycobacteria - analytical evaluation - phenylcarbamates - N-phenylpiperazine

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