Skip navigation

Please use this identifier to cite or link to this item:
Title: Investigation of hydro-lipophilic properties of n-alkoxyphenylhydroxynaphthalenecarboxamides
Authors: Kapustikova, Iva
Bąk, Andrzej
Gonec, Tomas
Kos, Jiri
Kozik, Violetta
Jampilek, Josef
Keywords: Hydroxynaphthalenecarboxamides; Lipophilicity determinations; Structure-lipophilicity relationships
Issue Date: 2018
Citation: Molecules, Vol. 23, iss. 7 (2018), Art. No. 1635
Abstract: 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 C18 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 (π) 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.
DOI: 10.3390/molecules23071635
ISSN: 1420-3049
Appears in Collections:Artykuły (WNŚiT)

Files in This Item:
File Description SizeFormat 
Kapustikova_Investigation_of_Hydro_lipophilic_properties.pdf1,01 MBAdobe PDFView/Open
Show full item record

Uznanie Autorstwa 3.0 Polska Creative Commons License Creative Commons