Lipophilicity Studies on Thiosemicarbazide Derivatives

Agata Paneth; Anna Hawrył; Tomasz Plech; Mirosław Hawrył; Ryszard Świeboda; Dominika Janowska; Monika Wujec; Piotr Paneth

doi:10.3390/molecules22060952

Lipophilicity Studies on Thiosemicarbazide Derivatives

Molecules. 2017 Jun 8;22(6):952. doi: 10.3390/molecules22060952.

Authors

Agata Paneth¹, Anna Hawrył², Tomasz Plech³, Mirosław Hawrył⁴, Ryszard Świeboda⁵, Dominika Janowska⁶, Monika Wujec⁷, Piotr Paneth⁸

Affiliations

¹ Department of Organic Chemistry, Medical University, Chodźki 4a, 20-093 Lublin, Poland. agata.paneth@umlub.pl.
² Department of Inorganic Chemistry, Medical University, Chodźki 4a, 20-093 Lublin, Poland. anna.hawryl@umlub.pl.
³ Department of Organic Chemistry, Medical University, Chodźki 4a, 20-093 Lublin, Poland. tomasz.plech@umlub.pl.
⁴ Department of Inorganic Chemistry, Medical University, Chodźki 4a, 20-093 Lublin, Poland. mirek.hawryl@umlub.pl.
⁵ Department of Inorganic Chemistry, Medical University, Chodźki 4a, 20-093 Lublin, Poland. ryszard.swieboda@umlub.pl.
⁶ Department of Organic Chemistry, Medical University, Chodźki 4a, 20-093 Lublin, Poland. dominika.hagel@gmail.com.
⁷ Department of Organic Chemistry, Medical University, Chodźki 4a, 20-093 Lublin, Poland. monika.wujec@umlub.pl.
⁸ Institute of Applied Radiation Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Łódź, Poland. piotr.paneth@p.lodz.pl.

Abstract

The lipophilicity of two series of thiosemicarbazide derivatives was assessed by the RP-HPLC method with the RP-18 chromatographic column and the methanol-water mixture as the mobile phase. Distribution coefficients logP_HPLC were compared to calculated values generated by commonly used AClogP software and quantum chemical calculations. The reliability of the predictions was evaluated using the correlation matrix and PCA. For 4-benzoylthiosemicarbazides, a high correlation between theoretical and experimental logP parameters was obtained using the XlogP3 algorithm, while for 4-aryl/(cyclohexyl)thiosemicarbazides, the XlogP2 parameter was strongly correlated with the experimentally obtained logP.

Keywords: PCA; RP-HPLC; bacterial type IIA topoisomerases; logP; thiosemicarbazide derivatives.

MeSH terms

Algorithms
Chromatography, High Pressure Liquid
Hydrophobic and Hydrophilic Interactions
Methanol / chemistry
Quantum Theory
Semicarbazides / chemical synthesis*
Semicarbazides / chemistry*
Semicarbazides / isolation & purification
Software
Water / chemistry*

Substances

Semicarbazides
Water
thiosemicarbazide
Methanol