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Investigation of Hydro-Lipophilic Properties of N-Alkoxyphenylhydroxynaphthalenecarboxamides

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University in Bratislava, Odbojarov 10, 83232 Bratislava, Slovakia
Department of Synthesis Chemistry, Faculty of Mathematics, Physics and Chemistry, University of Silesia, Szkolna 9, 40007 Katowice, Poland
Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Palackeho 1, 61242 Brno, Czech Republic
Authors to whom correspondence should be addressed.
Preliminary results were presented at The 21th Electronic Conference on Synthetic Organic Chemistry (ECSOC-21), 1–30 November 2017 (paper 4719).
Molecules 2018, 23(7), 1635;
Received: 5 June 2018 / Revised: 25 June 2018 / Accepted: 1 July 2018 / Published: 4 July 2018
(This article belongs to the Special Issue ECSOC-21)
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. View Full-Text
Keywords: hydroxynaphthalenecarboxamides; lipophilicity determinations; structure-lipophilicity relationships hydroxynaphthalenecarboxamides; lipophilicity determinations; structure-lipophilicity relationships
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MDPI and ACS Style

Kapustikova, I.; Bak, A.; Gonec, T.; Kos, J.; Kozik, V.; Jampilek, J. Investigation of Hydro-Lipophilic Properties of N-Alkoxyphenylhydroxynaphthalenecarboxamides . Molecules 2018, 23, 1635.

AMA Style

Kapustikova I, Bak A, Gonec T, Kos J, Kozik V, Jampilek J. Investigation of Hydro-Lipophilic Properties of N-Alkoxyphenylhydroxynaphthalenecarboxamides . Molecules. 2018; 23(7):1635.

Chicago/Turabian Style

Kapustikova, Iva, Andrzej Bak, Tomas Gonec, Jiri Kos, Violetta Kozik, and Josef Jampilek. 2018. "Investigation of Hydro-Lipophilic Properties of N-Alkoxyphenylhydroxynaphthalenecarboxamides " Molecules 23, no. 7: 1635.

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