Podrobný výpis o publikaci

KAPUSTIKOVA, I, A BAK, Tomáš GONĚC, J KOS, V KOZIK a J JAMPILEK. Investigation of Hydro-Lipophilic Properties of N-Alkoxyphenylhydroxynaphthalenecarboxamides. Molecules. BASEL: Mayer und Muller, 2018, roč. 23, č. 7, 15 s. ISSN 1420-3049. Dostupné z: https://dx.doi.org/10.3390/molecules23071635.

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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  -

Základní údaje
Originální název	Investigation of Hydro-Lipophilic Properties of N-Alkoxyphenylhydroxynaphthalenecarboxamides
Autoři	KAPUSTIKOVA, I, A BAK, Tomáš GONĚC, J KOS, V KOZIK a J JAMPILEK.
Vydání	Molecules, BASEL, Mayer und Muller, 2018, 1420-3049.

Další údaje
Originální jazyk	angličtina
Typ výsledku	Článek v odborném periodiku
Utajení	není předmětem státního či obchodního tajemství
Impakt faktor	Impact factor: 3.060
Doi	http://dx.doi.org/10.3390/molecules23071635
UT WoS	000445301800138
Klíčová slova anglicky	hydroxynaphthalenecarboxamides; lipophilicity determinations; structure-lipophilicity relationships
Příznaky	Mezinárodní význam, Recenzováno
Změnil	Změnil: PharmDr. Tomáš Goněc, Ph.D., učo 39112. Změněno: 9. 3. 2021 23:46.

Anotace
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.

Anotace

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.