(RS)-6,7-difluoro-3-(4-hydroxyphenyl)-3-(4-methoxyphenyl)indolin-2-one | 867155-00-8

• 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)-6,7-difluoro-3-(4-hydroxyphenyl)-3-(4-methoxyphenyl)indolin-2-one
• 英文别名: 6,7-difluoro-3-(4-hydroxy-phenyl)-3-(4-methoxy-phenyl)-1,3-dihydro-indol-2-one；6,7-difluoro-3-(4-hydroxyphenyl)-3-(4-methoxyphenyl)-1H-indol-2-one
• CAS: 867155-00-8
• 化学式: C₂₁H₁₅F₂NO₃
• 分子量: 367.352
• InChiKey: NDWXVRXJZNVDPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (RS)-6,7-difluoro-3-(4-hydroxyphenyl)-3-(4-methoxyphenyl)indolin-2-one 、 N,N-二甲基甘氨酸 在 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4,4'-(6,7-difluoro-2-oxoindoline-3,3-diyl)bis(4,1-phenylene) bis(2-dimethylamino)acetate
  参考文献：
  名称：

  WO2008/71387

  摘要：

  公开号：
• 作为产物：
  描述：

  6,7-difluoro-3-hydroxy-3-(4-methoxyphenyl)-1,3-dihydro-2H-indol-2-one 、 苯酚 在 对甲苯磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 以92%的产率得到(RS)-6,7-difluoro-3-(4-hydroxyphenyl)-3-(4-methoxyphenyl)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

文献信息

• [EN] PRODRUGS OF SUBSTITUTED 3-(4-HYDROXYPHENYL)-INDOLIN-2-ONES<br/>[FR] PROMÉDICAMENTS DE 3-(4-HYDROXYPHÉNYL)-INDOLIN-2-ONES SUBSTITUÉS
  申请人：TOPOTARGET AS

  公开号：WO2010109008A1

  公开（公告）日：2010-09-30

  The present application discloses novel prodrugs of substituted 3-(4-hydroxy-phenyl)-indolin-2-one compounds (oxindole compounds), and the use of such compounds for the preparation of a medicament for the treatment of cancer in a mammal. The prodrug compounds are of the formula (I).

  本申请公开了取代的3-(4-羟基苯基)-吲哚啉-2-酮化合物（氧吲哚化合物）的新型前药，以及利用这些化合物制备哺乳动物癌症治疗药物的用途。前药化合物的化学式为（I）。
• 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。
• DIPHENYL-INDOL-2-ON COMPOUNDS AND THEIR USE IN THE TREATMENT OF CANCER
  申请人：TopoTarget A/S

  公开号：EP1734951A2

  公开（公告）日：2006-12-27
• PRODRUGS OF DIPHENYL OX- INDOL- 2 -ONE COMPOUNDS FOR THE TREATMENT OF CANCERS
  申请人：Topo Target A/S

  公开号：EP2102158A1

  公开（公告）日：2009-09-23
• PRODRUGS OF DIPHENYL OX-INDOL-2-ONE COMPOUNDS
  申请人：Christensen Mette Knak

  公开号：US20100029646A1

  公开（公告）日：2010-02-04

  The present application discloses prodrugs of substituted 3,3-diphenyl-1,3-dihydro-indol-2-one compounds having the general formula (I). The 4-position of the phenyl moieties and the N-position of the indole represent useful handles for the introduction of particular prodrug groups, in particular those comprising an amino acid moiety. The prodrug compounds are believed to be useful for the treatment of cancer in a mammal, possibly in combination with one or more other chemotherapeutic agents. The application also discloses the compounds for use in a method of treating a mammal suffering from or being susceptible to cancer