4-[6-(2-Fluoro-phenyl)-[1,3]dioxolo[4,5-g]quinolin-8-yloxy]-butyric acid ethyl ester | 377740-09-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-[6-(2-Fluoro-phenyl)-[1,3]dioxolo[4,5-g]quinolin-8-yloxy]-butyric acid ethyl ester
• 英文别名: ethyl 4-[[6-(2-fluorophenyl)-[1,3]dioxolo[4,5-g]quinolin-8-yl]oxy]butanoate
• CAS: 377740-09-5
• 化学式: C₂₂H₂₀FNO₅
• 分子量: 397.403
• InChiKey: SXJPAUFFSLFCNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-[6-(2-Fluoro-phenyl)-[1,3]dioxolo[4,5-g]quinolin-8-yloxy]-butyric acid ethyl ester 在 10percent aq. NaOH 作用下， 反应 2.0h， 以82.5%的产率得到4-[6-(2-Fluoro-phenyl)-[1,3]dioxolo[4,5-g]quinolin-8-yloxy]-butyric acid
  参考文献：
  名称：

  Antitumor Agents. 211. Fluorinated 2-Phenyl-4-quinolone Derivatives as Antimitotic Antitumor Agents

  摘要：

  Fluorinated 2-phenyl-4-quinolone derivatives were synthesized and evaluated in National Cancer Institute's 60 human tumor cell line in vitro screen. From the results, the ketone moiety plays an essential role in activity. Among the compounds tested, 2'-fluoro-6-pyrrol-2-phenyl-4-quinolone (13) exhibited the most potent cytotoxic activities (log GI(50) < -8.00) against renal and melanoma tumor cell lines. Compound 13 was also a potent inhibitor of tubulin polymerization (IC50 = 0.46 muM) and of radiolabeled colchicine binding to tubulin, with activities comparable to those of the potent antimitotic natural products colchicine, podophyllotoxin, and combretastatin A-4.

  DOI：

  10.1021/jm0101085
• 作为产物：
  描述：

  邻氟苯甲酰氯 在 potassium tert-butylate 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 26.0h， 生成 4-[6-(2-Fluoro-phenyl)-[1,3]dioxolo[4,5-g]quinolin-8-yloxy]-butyric acid ethyl ester
  参考文献：
  名称：

  Antitumor Agents. 211. Fluorinated 2-Phenyl-4-quinolone Derivatives as Antimitotic Antitumor Agents

  摘要：

  Fluorinated 2-phenyl-4-quinolone derivatives were synthesized and evaluated in National Cancer Institute's 60 human tumor cell line in vitro screen. From the results, the ketone moiety plays an essential role in activity. Among the compounds tested, 2'-fluoro-6-pyrrol-2-phenyl-4-quinolone (13) exhibited the most potent cytotoxic activities (log GI(50) < -8.00) against renal and melanoma tumor cell lines. Compound 13 was also a potent inhibitor of tubulin polymerization (IC50 = 0.46 muM) and of radiolabeled colchicine binding to tubulin, with activities comparable to those of the potent antimitotic natural products colchicine, podophyllotoxin, and combretastatin A-4.

  DOI：

  10.1021/jm0101085

文献信息

• Antitumor Agents. 211. Fluorinated 2-Phenyl-4-quinolone Derivatives as Antimitotic Antitumor Agents
  作者：Yi Xia、Zheng-Yu Yang、Peng Xia、Torben Hackl、Ernest Hamel、Anthony Mauger、Jiu-Hong Wu、Kuo-Hsiung Lee

  DOI：10.1021/jm0101085

  日期：2001.11.1

  Fluorinated 2-phenyl-4-quinolone derivatives were synthesized and evaluated in National Cancer Institute's 60 human tumor cell line in vitro screen. From the results, the ketone moiety plays an essential role in activity. Among the compounds tested, 2'-fluoro-6-pyrrol-2-phenyl-4-quinolone (13) exhibited the most potent cytotoxic activities (log GI(50) < -8.00) against renal and melanoma tumor cell lines. Compound 13 was also a potent inhibitor of tubulin polymerization (IC50 = 0.46 muM) and of radiolabeled colchicine binding to tubulin, with activities comparable to those of the potent antimitotic natural products colchicine, podophyllotoxin, and combretastatin A-4.