We have synthesized a series of 2-phenyl-3-hydroxy-4(1H)-quinolinone derivatives substituted with one or more fluorine atoms on the quinolone backbone as well as on phenyl ring. The derivatives bearing more fluorine atoms were subjected to modification by nucleophilic substitutions by thiophenol, morpholine, and piperazine derivative. We have tested the prepared compounds in cytotoxic activity assay against cancer cell lines. Four derivatives exhibited micromolar values of IC50 against some of the cancer cell lines, and we have subjected them to cell cycle analysis on CCRF-CEM. Moreover, most active 7-fluoro-3-hydroxy-2-phenyl-6-(phenylthio)quinolin-4(1H)-one inhibits mitosis progression. Cell cycle analysis, in vitro tubulin polymerization assay, and tubulin imaging in cells indicated that the anticancer activity of thiophenol derivative is associated with its ability to inhibit microtubule formation.

中文翻译：

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2-苯基-3-羟基-4（1H）-喹啉酮的氟化衍生物作为微管蛋白聚合抑制剂。

我们已经合成了一系列的2-苯基-3-羟基-4（1H）-喹啉酮衍生物，这些衍生物在喹诺酮主链以及苯环上被一个或多个氟原子取代。带有更多氟原子的衍生物通过苯硫酚，吗啉和哌嗪衍生物的亲核取代进行修饰。我们已经在针对癌细胞系的细胞毒性活性测定中测试了所制备的化合物。四种衍生物对某些癌细胞系表现出IC50的微摩尔值，我们对它们进行了CCRF-CEM的细胞周期分析。此外，最活跃的7-氟-3-羟基-2-苯基-6-（苯硫基）喹啉-4（1H）-一个抑制有丝分裂的进程。细胞周期分析，体外微管蛋白聚合测定，