6-fluoro-4-hydroxy-3-(2-methoxyphenyl)quinolin-2(1H)-one | 124028-80-4

• 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: 6-fluoro-4-hydroxy-3-(2-methoxyphenyl)quinolin-2(1H)-one
• 英文别名: 6-fluoro-4-hydroxy-3-(2-methoxyphenyl)-2(1H)-quinolinone；6-Fluoro-4-hydroxy-3-(2-methoxyphenyl)carbostyril；6-fluoro-4-hydroxy-3-(2-methoxyphenyl)-1H-quinolin-2-one
• CAS: 124028-80-4
• 化学式: C₁₆H₁₂FNO₃
• 分子量: 285.275
• InChiKey: KGUAVPJCSADQKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-fluoro-4-hydroxy-3-(2-methoxyphenyl)quinolin-2(1H)-one 在 吡啶盐酸盐 作用下， 生成 2-fluorobenzofuro[3,2-c]quinolin-6(5H)-one
  参考文献：
  名称：

  Synthesis and cytotoxic activity evaluation of indolo-, pyrrolo-, and benzofuro-quinolin-2(1H)-ones and 6-anilinoindoloquinoline derivatives

  摘要：

  Certain indolo-, pyrrolo-, and benzofuro-quinolin-2(1H)-ones 4a,b, 6, 8, 16a-c and 6-anilinoindoloquinoline derivatives 10a,b, 11a,b, 12a,b have been synthesized and evaluated in vitro against a 3-cell lines panel consisting of MCF7 (Breast), NCI-H460 (Lung), and SF-268 (CNS). Those active compounds 4a,b, 6, 8, 10a,b, 11a,b, 12a,b were then evaluated in the full panel of 60 human tumor cell lines derived from nine cancer cell types. The results have shown that cytotoxicity decreases in the order of 6-anilinoindoloquinolines>indoloquinolin-2(1H)-ones>pyrroloquinolin-2(1H)-ones>benzofuroquinolin-2(1H)-ones. Among them, 1-[3-(11H-indolo[3,2-c]quinolin-6ylamino)phenyl]ethanone oxime hydrochloride (14a) and its 2-chloro derivative (11b) were most active, with mean GI(50) values of 1.70 and 1.35 muM, respectively. Both compounds 11a,b were also found to inhibit the growth of SNB-75 (CNS cancer cell) with a GI(50) value of less than 0.01 muM, and, therefore, were selected for further evaluation for in vivo antitumor activity. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(02)00111-6
• 作为产物：
  描述：

  邻甲氧基苯基丙二酸二乙酯 、 4-氟苯胺 以 二苯醚 为溶剂， 反应 1.0h， 以71%的产率得到6-fluoro-4-hydroxy-3-(2-methoxyphenyl)quinolin-2(1H)-one
  参考文献：
  名称：

  Yamaguchi, Seiji; Tsuzuki, Kunihiro; Kinoshita, Minoru, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 281 - 284

  摘要：

  DOI：

文献信息

• YAMAGUCHI, SEIJI;TSUZUKI, KUNIHIRO;KINOSHITA, MINORU;OH-HIRA, YUTAKA;KAWA+, J. HETEROCYCLIC CHEM., 26,(1989) N, C. 281-284
  作者：YAMAGUCHI, SEIJI、TSUZUKI, KUNIHIRO、KINOSHITA, MINORU、OH-HIRA, YUTAKA、KAWA+

  DOI：——

  日期：——
• Yamaguchi, Seiji; Tsuzuki, Kunihiro; Kinoshita, Minoru, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 281 - 284
  作者：Yamaguchi, Seiji、Tsuzuki, Kunihiro、Kinoshita, Minoru、Oh-hira, Yutaka、Kawase, Yoshiyuki

  DOI：——

  日期：——
• Synthesis and cytotoxic activity evaluation of indolo-, pyrrolo-, and benzofuro-quinolin-2(1H)-ones and 6-anilinoindoloquinoline derivatives
  作者：Yeh-Long Chen、Chao-Ho Chung、I.-Li Chen、Po-Hsu Chen、Haw-Yaun Jeng

  DOI：10.1016/s0968-0896(02)00111-6

  日期：2002.8

  Certain indolo-, pyrrolo-, and benzofuro-quinolin-2(1H)-ones 4a,b, 6, 8, 16a-c and 6-anilinoindoloquinoline derivatives 10a,b, 11a,b, 12a,b have been synthesized and evaluated in vitro against a 3-cell lines panel consisting of MCF7 (Breast), NCI-H460 (Lung), and SF-268 (CNS). Those active compounds 4a,b, 6, 8, 10a,b, 11a,b, 12a,b were then evaluated in the full panel of 60 human tumor cell lines derived from nine cancer cell types. The results have shown that cytotoxicity decreases in the order of 6-anilinoindoloquinolines>indoloquinolin-2(1H)-ones>pyrroloquinolin-2(1H)-ones>benzofuroquinolin-2(1H)-ones. Among them, 1-[3-(11H-indolo[3,2-c]quinolin-6ylamino)phenyl]ethanone oxime hydrochloride (14a) and its 2-chloro derivative (11b) were most active, with mean GI(50) values of 1.70 and 1.35 muM, respectively. Both compounds 11a,b were also found to inhibit the growth of SNB-75 (CNS cancer cell) with a GI(50) value of less than 0.01 muM, and, therefore, were selected for further evaluation for in vivo antitumor activity. (C) 2002 Published by Elsevier Science Ltd.