TY  - JOUR
AU  - Ciura, Krzesimir
AU  - Fedorowicz, Joanna
AU  - Andrić, Filip
AU  - Žuvela, Petar
AU  - Greber, Katarzyna Ewa
AU  - Baranowski, Paweł
AU  - Kawczak, Piotr
AU  - Nowakowska, Joanna
AU  - Baçzek, Tomasz
AU  - Saçzewski, Jarosław
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3764
AB  - The lipophilicity of a molecule is a well-recognized as a crucial physicochemical factor that conditions the biological activity of a drug candidate. This study was aimed to evaluate the lipophilicity of isoxazolo[3,4-b]pyridine-3(1H)-ones and their N1-substituted derivatives, which demonstrated pronounced antifungal activities. Several methods, including reversed-phase thin layer chromatography (RP-TLC), reversed phase high-performance liquid chromatography (RP-HPLC), and micellar electrokinetic chromatography (MEKC), were employed. Furthermore, the calculated logP values were estimated using various freely and commercially available software packages and online platforms, as well as density functional theory computations (DFT). Similarities and dissimilarities between the determined lipophilicity indices were assessed using several chemometric approaches. Principal component analysis (PCA) indicated that other features beside lipophilicity affect antifungal activities of the investigated derivatives. Quantitative-structure-retention-relationship (QSRR) analysis by means of genetic algorithm - partial least squares (GA-PLS) - was implemented to rationalize the link between the physicochemical descriptors and lipophilicity. Among the studied compounds, structure 16 should be considered as the best starting structure for further studies, since it demonstrated the lowest lipophilic character within the series while retaining biological activity. Sum of ranking differences (SRD) analysis indicated that the chromatographic approach, regardless of the technique employed, should be considered as the best approach for lipophilicity assessment of isoxazolones.
T2  - Molecules
T1  - Lipophilicity determination of antifungal isoxazolo[3,4-b]pyridin-3(1h)-ones and their n1-substituted derivatives with chromatographic and computational methods
VL  - 24
IS  - 23
SP  - 1
EP  - 22
DO  - 10.3390/molecules24234311
ER  - 

@article{
author = "Ciura, Krzesimir and Fedorowicz, Joanna and Andrić, Filip and Žuvela, Petar and Greber, Katarzyna Ewa and Baranowski, Paweł and Kawczak, Piotr and Nowakowska, Joanna and Baçzek, Tomasz and Saçzewski, Jarosław",
year = "2019",
abstract = "The lipophilicity of a molecule is a well-recognized as a crucial physicochemical factor that conditions the biological activity of a drug candidate. This study was aimed to evaluate the lipophilicity of isoxazolo[3,4-b]pyridine-3(1H)-ones and their N1-substituted derivatives, which demonstrated pronounced antifungal activities. Several methods, including reversed-phase thin layer chromatography (RP-TLC), reversed phase high-performance liquid chromatography (RP-HPLC), and micellar electrokinetic chromatography (MEKC), were employed. Furthermore, the calculated logP values were estimated using various freely and commercially available software packages and online platforms, as well as density functional theory computations (DFT). Similarities and dissimilarities between the determined lipophilicity indices were assessed using several chemometric approaches. Principal component analysis (PCA) indicated that other features beside lipophilicity affect antifungal activities of the investigated derivatives. Quantitative-structure-retention-relationship (QSRR) analysis by means of genetic algorithm - partial least squares (GA-PLS) - was implemented to rationalize the link between the physicochemical descriptors and lipophilicity. Among the studied compounds, structure 16 should be considered as the best starting structure for further studies, since it demonstrated the lowest lipophilic character within the series while retaining biological activity. Sum of ranking differences (SRD) analysis indicated that the chromatographic approach, regardless of the technique employed, should be considered as the best approach for lipophilicity assessment of isoxazolones.",
journal = "Molecules",
title = "Lipophilicity determination of antifungal isoxazolo[3,4-b]pyridin-3(1h)-ones and their n1-substituted derivatives with chromatographic and computational methods",
volume = "24",
number = "23",
pages = "1-22",
doi = "10.3390/molecules24234311"
}

Ciura, K., Fedorowicz, J., Andrić, F., Žuvela, P., Greber, K. E., Baranowski, P., Kawczak, P., Nowakowska, J., Baçzek, T.,& Saçzewski, J.. (2019). Lipophilicity determination of antifungal isoxazolo[3,4-b]pyridin-3(1h)-ones and their n1-substituted derivatives with chromatographic and computational methods. in Molecules, 24(23), 1-22.
https://doi.org/10.3390/molecules24234311

Ciura K, Fedorowicz J, Andrić F, Žuvela P, Greber KE, Baranowski P, Kawczak P, Nowakowska J, Baçzek T, Saçzewski J. Lipophilicity determination of antifungal isoxazolo[3,4-b]pyridin-3(1h)-ones and their n1-substituted derivatives with chromatographic and computational methods. in Molecules. 2019;24(23):1-22.
doi:10.3390/molecules24234311 .

Ciura, Krzesimir, Fedorowicz, Joanna, Andrić, Filip, Žuvela, Petar, Greber, Katarzyna Ewa, Baranowski, Paweł, Kawczak, Piotr, Nowakowska, Joanna, Baçzek, Tomasz, Saçzewski, Jarosław, "Lipophilicity determination of antifungal isoxazolo[3,4-b]pyridin-3(1h)-ones and their n1-substituted derivatives with chromatographic and computational methods" in Molecules, 24, no. 23 (2019):1-22,
https://doi.org/10.3390/molecules24234311 . .