Lipophilicity is a physicochemical property of an essential importance in medicinal chemistry; therefore, fast and reliable measurement of lipophilicity will affect greatly the drug discovery process. A series of N-benzenesulfonamide-1H-pyrazoles, oximes and hydrazones as celecoxib analogues was investigated with regard to their retention behavior using reversed-phase high performance liquid chromatography (RP-HPLC). The mobile phases employed for this study consist of a mixture of water and methanol in different proportions. In addition, the stationary phase utilized for this separation was C18 silanized silica gel and using 200 nm as a detection wavelength. The retention behavior of the investigated compounds was determined based on practical determination of log k at different concentrations of methanol (as an organic modifier) in the mobile phase ranging from 60 to 80%. It was observed that the retention of these compounds (expressed as log k) decreased in a linear manner with increasing the concentration of methanol. High correlation coefficients (more than 0.90 in most cases) were obtained for the relationship between the volume fraction of the organic solvent and the retention values represented as log kw. A comparative evaluation was carried out between chromatographically-obtained lipophilicity parameters (represented as lipophilicity chromatographic index log kw or isocratic chromatographic hydrophobicity index, $$\varphi$$ 0) and the computationally calculated log P values (miLogP, ALOGP, ACD/Labs and ALOGPs). It was found that a good correlation exists between the experimental and computed log P values. In the future, these results can give a deep insight about the anti-inflammatory and analgesic activity of the newly synthesized compounds.

中文翻译：

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使用反相 HPLC 评估新合成的塞来昔布类似物的亲脂性

亲脂性是药物化学中至关重要的物理化学性质；因此，快速可靠的亲脂性测量将极大地影响药物发现过程。使用反相高效液相色谱 (RP-HPLC) 研究了一系列作为塞来考昔类似物的 N-苯磺酰胺-1H-吡唑、肟和腙的保留行为。本研究使用的流动相由不同比例的水和甲醇的混合物组成。此外，用于该分离的固定相是C18硅烷化硅胶并使用200 nm作为检测波长。所研究化合物的保留行为是根据流动相中不同甲醇（作为有机改性剂）浓度（范围为 60% 至 80%）下 log k 的实际测定来确定的。据观察，随着甲醇浓度的增加，这些化合物的保留量（表示为 log k）以线性方式下降。有机溶剂的体积分数与以log kw 表示的保留值之间的关系获得了高相关系数（大多数情况下大于0.90）。对色谱获得的亲脂性参数（表示为亲脂性色谱指数 log kw 或等度色谱疏水性指数，$$\varphi$$ 0）和计算计算的 log P 值（miLogP、ALOGP、ACD/Labs 和ALOGP）。结果发现，实验和计算的 log P 值之间存在良好的相关性。将来，这些结果可以深入了解新合成化合物的抗炎和镇痛活性。