5-fluoro-3,3-bis(5-methoxy-1H-indol-3-yl)-1H-indol-2-one | 1248586-44-8

• 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: 5-fluoro-3,3-bis(5-methoxy-1H-indol-3-yl)-1H-indol-2-one
• CAS: 1248586-44-8
• 化学式: C₂₆H₂₀FN₃O₃
• 分子量: 441.462
• InChiKey: CESOMIMDWKQMDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  79.1
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-甲氧基吲哚 、 5-氟靛红 在 iron(III) chloride 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以78%的产率得到5-fluoro-3,3-bis(5-methoxy-1H-indol-3-yl)-1H-indol-2-one
  参考文献：
  名称：

  Synthesis of 3,3-diindolyl oxyindoles efficiently catalysed by FeCl3 and their in vitro evaluation for anticancer activity

  摘要：

  A simple and highly efficient method has been developed for the synthesis of 3,3-diindolyl oxyindoles by the reaction of indoles with isatin or 5-fluoro isatin using a catalytic amount (5 mol %) of FeCl3 at room temperature in a short reaction time in high yields. All these compounds were evaluated against a panel of five human cancer lines and most of them showed potent cytotoxicity. Compound 4b showed IC50 of 4.7 and 5 mu M against SK-N-SH and DU-145 cell lines, respectively, whereas 4c, 4d, 4f and 4k showed IC50 of 2.2, 1.2, 3.6 and 3.6 mu M, respectively, against DU-145 cell line. Interestingly, some of the compounds are selectively potent in prostate cancer (DU-145) with IC50 values of 1.2-19.6 mu M. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.152

文献信息

• Synthesis of 3,3-diindolyl oxyindoles efficiently catalysed by FeCl3 and their in vitro evaluation for anticancer activity
  作者：Ahmed Kamal、Y.V.V. Srikanth、M. Naseer A. Khan、Thokhir Basha Shaik、Md. Ashraf

  DOI：10.1016/j.bmcl.2010.06.152

  日期：2010.9

  A simple and highly efficient method has been developed for the synthesis of 3,3-diindolyl oxyindoles by the reaction of indoles with isatin or 5-fluoro isatin using a catalytic amount (5 mol %) of FeCl3 at room temperature in a short reaction time in high yields. All these compounds were evaluated against a panel of five human cancer lines and most of them showed potent cytotoxicity. Compound 4b showed IC50 of 4.7 and 5 mu M against SK-N-SH and DU-145 cell lines, respectively, whereas 4c, 4d, 4f and 4k showed IC50 of 2.2, 1.2, 3.6 and 3.6 mu M, respectively, against DU-145 cell line. Interestingly, some of the compounds are selectively potent in prostate cancer (DU-145) with IC50 values of 1.2-19.6 mu M. (C) 2010 Elsevier Ltd. All rights reserved.