(RS)-3-(3,4-difluorophenyl)-6,7-difluoro-3-hydroxyindolin-2-one | 1073262-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (RS)-3-(3,4-difluorophenyl)-6,7-difluoro-3-hydroxyindolin-2-one
• 英文别名: 3-(3,4-difluorophenyl)-6,7-difluoro-3-hydroxyindolin-2-one；3-(3,4-difluorophenyl)-6,7-difluoro-3-hydroxy-1H-indol-2-one
• CAS: 1073262-08-4
• 化学式: C₁₄H₇F₄NO₂
• 分子量: 297.209
• InChiKey: WJCBLKUDWLYJNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (RS)-3-(3,4-difluorophenyl)-6,7-difluoro-3-hydroxyindolin-2-one 、 苯酚 在 对甲苯磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 以98%的产率得到(RS)-3-(3,4-difluorophenyl)-6,7-difluoro-3-(4-hydroxyphenyl)indolin-2-one
  参考文献：
  名称：

  Synthesis and Antitumor Effect in Vitro and in Vivo of Substituted 1,3-Dihydroindole-2-ones

  摘要：

  Optimization of the anticancer activity for a class of compounds built on a 1,3-dihydroindole-2-one scaffold was performed. In comparison with recently published derivatives of oxyphenisatin the new analogues exhibited an equally potent antiproliferative activity in vitro and improved tolerability and activity in vivo. The best compounds from this series showed low nanomolar antiproliferative activity toward a series of cancer cell lines (compound (S)-38: IC(50) of 0.48 and 2 nM in MCF-7 (breast) and PC3 (prostate), respectively) and potent antitumor effects in well tolerated doses in xenograft models. The racemic compound (R.S)-38 showed complete tumor regression at a dose of 20 mg/kg administered iv on days 1 and 7 in a PC3 rat xenograft.

  DOI：

  10.1021/jm100763j
• 作为产物：
  描述：

  6,7-二氟-1H-吲哚-2,3-二酮 、 magnesium,1,2-difluorobenzene-5-ide,bromide 以 四氢呋喃 为溶剂， 反应 0.5h， 以60%的产率得到(RS)-3-(3,4-difluorophenyl)-6,7-difluoro-3-hydroxyindolin-2-one
  参考文献：
  名称：

  Synthesis and Antitumor Effect in Vitro and in Vivo of Substituted 1,3-Dihydroindole-2-ones

  摘要：

  Optimization of the anticancer activity for a class of compounds built on a 1,3-dihydroindole-2-one scaffold was performed. In comparison with recently published derivatives of oxyphenisatin the new analogues exhibited an equally potent antiproliferative activity in vitro and improved tolerability and activity in vivo. The best compounds from this series showed low nanomolar antiproliferative activity toward a series of cancer cell lines (compound (S)-38: IC(50) of 0.48 and 2 nM in MCF-7 (breast) and PC3 (prostate), respectively) and potent antitumor effects in well tolerated doses in xenograft models. The racemic compound (R.S)-38 showed complete tumor regression at a dose of 20 mg/kg administered iv on days 1 and 7 in a PC3 rat xenograft.

  DOI：

  10.1021/jm100763j

文献信息

• SUBSTITUTED 3-(4-HYDROXYPHENYL)-INDOLIN-2-ONE COMPOUNDS
  申请人：Christensen Mette Knak

  公开号：US20100227863A1

  公开（公告）日：2010-09-09

  The present application discloses substituted 3-(4-hydroxyphenyl)-indolin-2-one compounds (oxindole compounds) of the formula and the use of such compounds for the preparation of a medicament for the treatment of cancer in a mammal, in particular in humans.

  本申请公开了代替3-(4-羟基苯基)-吲哚-2-酮化合物（氧化吲哚化合物）的公式以及使用这种化合物制备哺乳动物，特别是人类的肿瘤药物的用途。
• [EN] SUBSTITUTED 3-(4-HYDROXYPHENYL)-INDOLIN-2-ONE-COMPOUNDS<br/>[FR] COMPOSÉS 3-(4-HYDROXYPHÉNYL)-INDOLIN-2-ONE SUBSTITUÉS
  申请人：TOPOTARGET AS

  公开号：WO2008129075A1

  公开（公告）日：2008-10-30

  [EN] The present application discloses substituted 3-(4-hydroxyphenyl)-indolin-2-one compounds(oxindole compounds) of the Formula (I) and the use of such compounds for the preparation of a medicament for the treatment of cancer in a mammal, in particular in humans.
  [FR] La présente invention porte sur des composés 3-(4-hydroxyphényl)-indolin-2-one substitués (composés d'oxindole) de la Formule (I) et sur l'utilisation de ces composés pour la préparation d'un médicament pour le traitement du cancer chez un mammifère, en particulier chez les êtres humains.
• Synthesis and Antitumor Effect in Vitro and in Vivo of Substituted 1,3-Dihydroindole-2-ones
  作者：Mette K. Christensen、Kamille D. Erichsen、Christina Trojel-Hansen、Jette Tjørnelund、Søren J. Nielsen、Karla Frydenvang、Tommy N. Johansen、Birgitte Nielsen、Maxwell Sehested、Peter B. Jensen、Martins Ikaunieks、Andrei Zaichenko、Einars Loza、Ivars Kalvinsh、Fredrik Björkling

  DOI：10.1021/jm100763j

  日期：2010.10.14

  Optimization of the anticancer activity for a class of compounds built on a 1,3-dihydroindole-2-one scaffold was performed. In comparison with recently published derivatives of oxyphenisatin the new analogues exhibited an equally potent antiproliferative activity in vitro and improved tolerability and activity in vivo. The best compounds from this series showed low nanomolar antiproliferative activity toward a series of cancer cell lines (compound (S)-38: IC(50) of 0.48 and 2 nM in MCF-7 (breast) and PC3 (prostate), respectively) and potent antitumor effects in well tolerated doses in xenograft models. The racemic compound (R.S)-38 showed complete tumor regression at a dose of 20 mg/kg administered iv on days 1 and 7 in a PC3 rat xenograft.