Musiol Robert, Jampilek Josef, Buchta Vladimir, Silva Luis, Niedbala Halina, Podeszwa Barbara, Palka Anna, Majerz-Maniecka Katarzyna, Oleksyn Barbara, Polanski Jaroslaw
Institute of Chemistry, University of Silesia, Szkolna 9, 40007 Katowice, Poland.
Bioorg Med Chem. 2006 May 15;14(10):3592-8. doi: 10.1016/j.bmc.2006.01.016. Epub 2006 Feb 3.
The series of quinoline derivatives were prepared. The synthetic approach, analytical, and spectroscopic data of all synthesized compounds are presented. All the prepared derivatives were analyzed using the reversed-phase high performance liquid chromatography (RP-HPLC) method for the lipophilicity measurement. In the present study, the correlation between RP-HPLC retention parameter log K (the logarithm of capacity factor K) and various calculated log P data is shown. The relationships between the lipophilicity and the chemical structure of the studied compounds are discussed as well. The prepared compounds were tested for their in vitro antifungal activity. 2-[(3-Hydroxyphenylimino)methyl]quinolin-8-ol (8), 2-[(4-hydroxyphenylimino)methyl]quinolin-8-ol (9) and 2-[(2,5-dichloro-4-nitrophenylamino)methoxymethyl]quinolin-8-ol (10) showed in vitro antifungal activity comparable to or higher than that of the standard fluconazole. Structure-activity relationships among the chemical structure, the physical properties, and the biological activities of the evaluated compounds are discussed in the article.
制备了一系列喹啉衍生物。给出了所有合成化合物的合成方法、分析和光谱数据。使用反相高效液相色谱（RP-HPLC）法对所有制备的衍生物进行分析以测定亲脂性。在本研究中，展示了RP-HPLC保留参数log K（容量因子K的对数）与各种计算得到的log P数据之间的相关性。还讨论了所研究化合物的亲脂性与化学结构之间的关系。对制备的化合物进行了体外抗真菌活性测试。2-[(3-羟基苯基亚氨基)甲基]喹啉-8-醇（8）、2-[(4-羟基苯基亚氨基)甲基]喹啉-8-醇（9）和2-[(2,5-二氯-4-硝基苯基氨基)甲氧基甲基]喹啉-8-醇（10）显示出与标准氟康唑相当或更高的体外抗真菌活性。文章中讨论了所评估化合物的化学结构、物理性质和生物活性之间的构效关系。
