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@article{1727097,
author = {Kapustikova, I and Bak, A and Goněc, Tomáš and Kos, J and Kozik, V and Jampilek, J},
article_location = {BASEL},
article_number = {7},
doi = {http://dx.doi.org/10.3390/molecules23071635},
keywords = {hydroxynaphthalenecarboxamides; lipophilicity determinations; structure-lipophilicity relationships},
language = {eng},
issn = {1420-3049},
journal = {Molecules},
title = {Investigation of Hydro-Lipophilic Properties of N-Alkoxyphenylhydroxynaphthalenecarboxamides},
volume = {23},
year = {2018}
}
TY - JOUR
ID - 1727097
AU - Kapustikova, I - Bak, A - Goněc, Tomáš - Kos, J - Kozik, V - Jampilek, J
PY - 2018
TI - Investigation of Hydro-Lipophilic Properties of N-Alkoxyphenylhydroxynaphthalenecarboxamides
JF - Molecules
VL - 23
IS - 7
PB - Mayer und Muller
SN - 14203049
KW - hydroxynaphthalenecarboxamides
KW - lipophilicity determinations
KW - structure-lipophilicity relationships
N2 - The evaluation of the lipophilic characteristics of biologically active agents is indispensable for the rational design of ADMET-tailored structure-activity models. N-Alkoxy-3-hydroxynaphthalene-2-carboxanilides, N-alkoxy-1-hydroxynaphthalene-2-carboxanilides, and N-alkoxy-2-hydroxynaphthalene-1-carboxanilides were recently reported as a series of compounds with antimycobacterial, antibacterial, and herbicidal activity. As it was found that the lipophilicity of these biologically active agents determines their activity, the hydro-lipophilic properties of all three series were investigated in this study. All 57 anilides were analyzed using the reversed-phase high-performance liquid chromatography method for the measurement of lipophilicity. The procedure was performed under isocratic conditions with methanol as an organic modifier in the mobile phase using an end-capped non-polar C-18 stationary reversed-phase column. In the present study, a range of software lipophilicity predictors for the estimation of clogP values of a set of N-alkoxyphenylhydroxynaphthalenecarboxamides was employed and subsequently cross-compared with experimental parameters. Thus, the empirical values of lipophilicity (logk) and the distributive parameters (pi) were compared with the corresponding in silico characteristics that were calculated using alternative methods for deducing the lipophilic features. To scrutinize (dis)similarities between the derivatives, a PCA procedure was applied to visualize the major differences in the performance of molecules with respect to their lipophilic profile, molecular weight, and violations of Lipinski's Rule of Five.
ER -
KAPUSTIKOVA, I, A BAK, Tomáš GONĚC, J KOS, V KOZIK and J JAMPILEK. Investigation of Hydro-Lipophilic Properties of N-Alkoxyphenylhydroxynaphthalenecarboxamides. \textit{Molecules}. BASEL: Mayer und Muller, 2018, vol.~23, No~7, 15 pp. ISSN~1420-3049. Available from: https://dx.doi.org/10.3390/molecules23071635.
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