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Evaluation of the lipophilicity of chalcones by RP-TLC and computational methods

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Abstract

Retention behaviour of twenty-one chalcones synthesized in our laboratory was tested in three thin-layer chromatography (RP-TLC) systems (acetonitrile–water, ethanol–water and acetone–water) and chromatography parameters \( {R}_M^0 \), S and C0 were calculated. The most suitable RP-TLC system (acetonitrile–water) and chromatography parameter (C0) for lipophilicity prediction of tested compounds were selected on the basis of the highest correlations with calculated logP values. In selected system, compound 12 had the highest, whereas 47 had the lowest C0 value. QSRR analysis was performed and three models representing relationships between C0 and selected molecular descriptors were created—MLR(C0), PLS(C0) and SVM(C0). Interpretation of molecular descriptors which form statistically the most reliable SVM(C0) model identified the most important structural and physico-chemical properties that influence retention behaviour of tested compounds. In addition, descriptors with the highest influence on \( {R}_M^0 \) as well as on C0 calculated in the remaining two RP-TLC systems were identified and interpreted.

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Funding

This work was financially supported by the Ministry of Education, Science and Technological Development, Republic of Serbia, as part of Project No.172041.

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, Belgrade, 11000, Serbia

    Vladimir Dobričić, Nemanja Turković, Branka Ivković, Oszkár Csuvik & Zorica Vujić

  2. Agency for Medicines and Medical Devices of Montenegro, 64A Bulevar Ivana Crnojevića, 81000, Podgorica, Montenegro

    Nemanja Turković

  3. Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, Szeged, 6720, Hungary

    Oszkár Csuvik

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  1. Vladimir Dobričić
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Correspondence to Vladimir Dobričić.

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Dobričić, V., Turković, N., Ivković, B. et al. Evaluation of the lipophilicity of chalcones by RP-TLC and computational methods. JPC-J Planar Chromat 33, 245–253 (2020). https://doi.org/10.1007/s00764-020-00029-w

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