9H-fluoren-9-ylmethyl N-(1H-indol-5-yl)carbamate | 1359086-12-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9H-fluoren-9-ylmethyl N-(1H-indol-5-yl)carbamate
• CAS: 1359086-12-6
• 化学式: C₂₃H₁₈N₂O₂
• 分子量: 354.408
• InChiKey: JWIRRDASTRCRSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9H-fluoren-9-ylmethyl N-(1H-indol-5-yl)carbamate 、 对苯二甲醛 在 碘 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 以60%的产率得到9H-fluoren-9-ylmethyl N-[3-[[4-[bis[5-(9H-fluoren-9-ylmethoxycarbonylamino)-1H-indol-3-yl]methyl]phenyl]-[5-(9H-fluoren-9-ylmethoxycarbonylamino)-1H-indol-3-yl]methyl]-1H-indol-5-yl]carbamate
  参考文献：
  名称：

  Synthesis and Evaluation of the Cytotoxicities of Tetraindoles: Observation that the 5-Hydroxy Tetraindole (SK228) Induces G₂ Arrest and Apoptosis in Human Breast Cancer Cells

  摘要：

  Current chemical and biological interest in indole-3-carbinol (I3C) and its metabolites has resulted in the discovery of new biologically active indoles. As part of a program aimed at the development of indole analogues, tetraindoles 1-15 were prepared and their antiproliferative effects on human breast cancer cells were evaluated. The results show that the 5-hydroxy-tetraindole 8 (SK228) has optimum antiproliferative activity against breast adenocarcinoma (MCF 7 and MDA-MB-231) cells and that this activity involves G(2)-phase arrest of the cell cycle with a distinctive increase in the expression of cyclin B1 and phospho-cdc2. Further observations suggest that 5-hydroxy-tetraindole 8 induces apoptosis through externalization of membrane phosphatidylserine, DNA fragmentation, and activation of caspase-3. Given the fact that I3C and its metabolites have been shown to improve therapeutic efficacy and to have a broad range of antitumor activities in human cancer cells, the current findings have important pharmacological relevance as they open a promising route to the development of a potential chemotherapeutic application of tetraindoles as agents for the treatment of breast cancer.

  DOI：

  10.1021/jm2013425
• 作为产物：
  描述：

  5-氨基吲哚 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以80%的产率得到9H-fluoren-9-ylmethyl N-(1H-indol-5-yl)carbamate
  参考文献：
  名称：

  Synthesis and Evaluation of the Cytotoxicities of Tetraindoles: Observation that the 5-Hydroxy Tetraindole (SK228) Induces G₂ Arrest and Apoptosis in Human Breast Cancer Cells

  摘要：

  Current chemical and biological interest in indole-3-carbinol (I3C) and its metabolites has resulted in the discovery of new biologically active indoles. As part of a program aimed at the development of indole analogues, tetraindoles 1-15 were prepared and their antiproliferative effects on human breast cancer cells were evaluated. The results show that the 5-hydroxy-tetraindole 8 (SK228) has optimum antiproliferative activity against breast adenocarcinoma (MCF 7 and MDA-MB-231) cells and that this activity involves G(2)-phase arrest of the cell cycle with a distinctive increase in the expression of cyclin B1 and phospho-cdc2. Further observations suggest that 5-hydroxy-tetraindole 8 induces apoptosis through externalization of membrane phosphatidylserine, DNA fragmentation, and activation of caspase-3. Given the fact that I3C and its metabolites have been shown to improve therapeutic efficacy and to have a broad range of antitumor activities in human cancer cells, the current findings have important pharmacological relevance as they open a promising route to the development of a potential chemotherapeutic application of tetraindoles as agents for the treatment of breast cancer.

  DOI：

  10.1021/jm2013425

文献信息

• Synthesis and Evaluation of the Cytotoxicities of Tetraindoles: Observation that the 5-Hydroxy Tetraindole (SK228) Induces G₂ Arrest and Apoptosis in Human Breast Cancer Cells
  作者：Wen-Shan Li、Chie-Hong Wang、Shengkai Ko、Tzu Ting Chang、Ya Ching Jen、Ching-Fa Yao、Shivaji V. More、Shu-Chuan Jao

  DOI：10.1021/jm2013425

  日期：2012.2.23

  Current chemical and biological interest in indole-3-carbinol (I3C) and its metabolites has resulted in the discovery of new biologically active indoles. As part of a program aimed at the development of indole analogues, tetraindoles 1-15 were prepared and their antiproliferative effects on human breast cancer cells were evaluated. The results show that the 5-hydroxy-tetraindole 8 (SK228) has optimum antiproliferative activity against breast adenocarcinoma (MCF 7 and MDA-MB-231) cells and that this activity involves G(2)-phase arrest of the cell cycle with a distinctive increase in the expression of cyclin B1 and phospho-cdc2. Further observations suggest that 5-hydroxy-tetraindole 8 induces apoptosis through externalization of membrane phosphatidylserine, DNA fragmentation, and activation of caspase-3. Given the fact that I3C and its metabolites have been shown to improve therapeutic efficacy and to have a broad range of antitumor activities in human cancer cells, the current findings have important pharmacological relevance as they open a promising route to the development of a potential chemotherapeutic application of tetraindoles as agents for the treatment of breast cancer.