Lipophilicity Evaluation of the Products Obtained in the Reaction of N3-Substituted Amidrazones with cis-1,2-Cyclohexanedicarboxylic Anhydride |
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Authors: | Ucherek Marzena Komsta ukasz Skibiski Robert Modzelewska-Banachiewicz Boena Gumieniczek Anna |
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Institution: | 1.Department of Organic Chemistry, Collegium Medicum, Nicolaus Copernicus University, Sklodowskiej-Curie 9, 85-094, Bydgoszcz, Poland ;2.Department of Medicinal Chemistry, Medical University of Lublin, Jaczewskiego 4, 20-090, Lublin, Poland ; |
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Abstract: | The lipophilicity of the novel 12 products of the reaction of N3-substituted amidrazones with cis-1,2-cyclohexanedicarboxylic anhydride (4 linear, 4 triazole-like and 4 isoindole ones) with potential pharmacologic activity was evaluated by thin layer and liquid chromatography. Using organic-aqueous eluent systems (with methanol or acetonitrile) on RP18 plates and C18 column, a linear relationship between the volume fraction of modifiers and the retention indices was obtained. The retention values, log k or R
M
were extrapolated to zero organic modifier content to obtain the log k
w or R
MW
values. 12 compounds with known literature lipophilicity were used as a calibration dataset. The results were compared in a multivariate way with in silico methods (ALOGPs, AC_logP, AB/LogP, COSMOFrag, miLogP, ALOGP, MLOGP, KOWWIN, XLOGP3). |
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