Publication details
Hydro-lipophilic Properties of Chlorinated and Brominated 1-Hydroxynaphthalene-2-carboxanilides.
| Authors | |
|---|---|
| Year of publication | 2024 |
| Type | Article in Proceedings |
| MU Faculty or unit | |
| Citation | |
| web | https://www.mdpi.com/2673-4583/16/1/26/pdf |
| Doi | https://doi.org/10.3390/ecsoc-28-20151 |
| Keywords | hydroxynaphthalene-carboxanilides; lipophilicity determinations; structure–lipophilicity relationships |
| Description | 1-Hydroxy-N-phenylnaphthalene-2-carboxamide and a series of seventeen other carboxanilides in the anilide part of dichlorinated, trichlorinated, dibrominated, tribrominated, and chlorinated/ brominated variants have recently been reported as biologically active compounds mainly with antibacterial, antimycobacterial, and anticancer effects. Since lipophilicity is one of the factors influencing the bioavailability (absorption, distribution, metabolism, and elimination), activity, and even toxicity of bioactive compounds, all the derivatives were investigated for their lipophilic and hydrophilic properties. All eighteen compounds were analyzed by reversed-phase high-performance liquid chromatography (RP-HPLC). The procedure was performed under isocratic conditions with methanol as the organic modifier in the mobile phase using an end-capped non-polar C18 stationary reversed-phase column. The lipophilicity values are expressed as the logarithm of the capacity factor k (for the mobile phase water/methanol) and the distribution coefficients D at pH values of 6.5 and 7.4 (for the mobile phase buffer/methanol), as well as the calculated values of log P/Clog P by various methods. 1-Hydroxy-N-(3,4,5-trichlorophenyl)naphtha- lene-2-carboxamide and N-(4-bromo-3- chlorophenyl)-1-hydroxynaphthalene-2-carboxamide are the most lipophilic compounds of the whole series; on the other hand, surprisingly, unsubstituted 1-hydroxy-N-phenylnaphthalene-2-carboxamide is not the least lipophilic derivative. The mutual correlations between the experimental and predicted lipophilicity values are low; in addition, there are large deviations in the cross-correlations between log k and log D, which are due to the presence of a free ionizable phenolic group in the molecule. |