Synthesis, spectral description, and lipophilicity parameters determination of phenylcarbamic acid derivatives with integrated N-phenylpiperazine moiety in the structure

Abstract

The phenylcarbamic acid derivatives with N-phenylpiperazine moiety in the molecule have been prepared. The structure has been confirmed by elemental analysis, IR, 1H NMR, and mass spectral data. For the prepared set of the compounds the lipophilicity parameters have been determined. The experimentally obtained lipophilicity parameters have been correlated with theoretical entries obtained by different computer programs based on the neural network and fragmental methods.

Antimicrobial activity of meta-alkoxyphenylcarbamates containing substituted N-phenylpiperazine fragment

“…The preparation of evaluated compounds, labelled as 6d-6g and 8c-8e (Table 1), their spectral characteristics ( 1 H NMR, 13 C NMR, IR, MS, UV/VIS) as well as the elemental analyses data were published previously (9,10). The procedures of physicochemical parameters determination (surface activity γ, dissociation constant pK a , lipophilicity descriptors -log P exp estimated by the shake-flask method in the octan-1-ol/ buffer medium with pH = 7,3, log k´ from RP-HPLC, R M from RP-TLC) and the corresponding readouts and conclusions were published in paper of Malík et al (11).…”

The in Vitro Antioxidant Properties of 2-Alkoxyphenylcarbamic Acid Derivatives Containing a 4´-(Substituted Phenyl)piperazin-1´-Yl Moiety Determined by the 2,2´-Azinobis(3-Ethylbenzothiazoline-6-Sulfonic Acid) Derived Radical Cation (Abts•+) and Ferric Re

“…As mentioned, both compounds 2 and 4 have shown a high lipophilicity, the log Pexp=3.90 was estimated for the substance 2, the log Pexp=3.60 was related to the derivative 4 (Malík et al 2005;Malík et al, 2006). On the other hand, the ATN and CRV reference drugs were slightly more prospective with the AAE=1.82±0.12mg/mL (ATN) and 2.03±0.14mg/mL (CRV; Table II).…”

“…It was found that the presence of the 4´-F substituent provided higher values of the compounds' pKa, which were observed in the range of 6.58 (2) to 6.73 (1). The introduction of a 3´-CF3 moiety led to lower pKas, namely the pKa=5.83 was estimated for the substance 3 and the pKa=6.00 was found for the derivative 4 (Malík et al, 2005;Malík et al, 2006).…”

“…The currently in vitro screened compounds 1-4 (Figure 1), chemically 1-[3-(2--methoxyphenylcarbamoyl)oxy-2-hydroxypropyl]-4-(4-fluorophenyl)piperazin-1-ium chloride (1), 1-[3-(2-ethoxyphenylcarbamoyl)oxy-2-hydroxypropyl]-4-(4-fluorophenyl)piperazin-1-ium chloride (2), 1-{2-hydroxy-3-(2-methoxyphenylcarbamoyl)oxy)propyl}-4-(3-trifluoromethylphenyl)piperazin-1-ium chloride (3) and 1-{2--hydroxy-3-(2-ethoxyphenylcarbamoyl)oxy)-propyl}-4-(3-trifluoromethylphenyl)piperazine--1-ium chloride (4), were synthesized previously (Malík et al, 2004;Malík et al, 2006). Their experimentally observed pKa values, which were determined by a potentiometric titration, and the log Pexps estimated by a classical shake flask method (Table I) were already published in the research papers of Malík et al (2005;.…”

“…In addition, the derivatives 1-4 were regarded as highly lipophilic compounds (Malík et al 2005;Malík et al, 2006) with the log Pexp values in the range of 3.57 (3) to 3.90 (2), as listed (Table I). Their lipophilicity was comparable to those of carvedilol with log Pexp=3.40 estimated in the octan-1--ol/buffer partitioning system (Yue et al, 1992).…”