Reversed-Phase TLC Study of the Lipophilicity of Fourteen 1,3-Benzoxazol-2(3H)-one Derivatives and Comparison with Isomeric 1,2-Benzisoxazol-3(2H)-one Analogs

摘要

The lipophilicity and specific hydrophobic surface area of fourteen l,3-benzoxazol-2(3H)-ones substituted in the benzene ring (fluoro-, chloro-, bromo-, dibromo-, amino-, and nitro-derivatives) were studied by reversed-phase thin-layer chromatography. Precoated C_18 F_254 plates and mixtures of methanol-water and aminoacetic acid buffer, pH 2.67 and 11.6, were used. The linear correlation between the volume fraction of methanol and values over a limited range was established with high values of correlation coefficients (f>0.98).The obtained results were compared with computationally calculated partition coefficients values (AlogPs, ClogP, AB/logP, milogP, logPKOWIN, AlogP2, XlogP3) by principal component analysis (PCA) and appreciable differences between them were observed. The comparison of chromatographic behavior of the investigated l,3-benzoxazol-2(3H)-ones with their isomeric analogs 1,2-benzisox-azol-3(2H)-ones shows significant differences between their R_M0 values.