di-(5-fluoroindol-3-yl)disulfide | 1093179-38-4

• 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: di-(5-fluoroindol-3-yl)disulfide
• 英文别名: 5-fluoro-3-[(5-fluoro-1H-indol-3-yl)disulfanyl]-1H-indole
• CAS: 1093179-38-4
• 化学式: C₁₆H₁₀F₂N₂S₂
• 分子量: 332.398
• InChiKey: BOINTPIZZVBYIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-氟吲哚 在 硫脲 、 碘 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以41%的产率得到di-(5-fluoroindol-3-yl)disulfide
  参考文献：
  名称：

  Structural characterization of di-indol-3-yl disulfide derivatives, potential antitumoral agents

  摘要：

  Di-5-X-indol-3-yl disulfides (X - H 1, F 2, Br 3, 14, OCH3 5) were synthesized and their solid state structures were probed by C-13 CP/MAS NMR spectroscopy. All disulfides adopt a layered conformation and both indole rings in one molecule were assumed to have very similar structural parameters, which is in agreement with a simple spectral pattern. For compounds I and 5 X-ray diffraction results are also presented. In the crystals of 1 and 5, the packing of the molecules is stabilized by dissimilar weak intermolecular interactions: in 1 dominate the N1-H1 center dot center dot center dot pi intermolecular hydrogen bonds and in 5 the C2-H2 center dot center dot center dot O10 intermolecular hydrogen bonds predominate. The di-5-fluoroindol-3-yl disulfide 2 and di-5-iodoindol-3-yl disulfide 4 were found to reduce considerably the growth of prostate cancer cell PC-3. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2008.04.033

文献信息

• Structural characterization of di-indol-3-yl disulfide derivatives, potential antitumoral agents
  作者：Maria Niemyjska、Dorota Maciejewska、Irena Wolska、Jolanta Soczewka

  DOI：10.1016/j.molstruc.2008.04.033

  日期：2008.11

  Di-5-X-indol-3-yl disulfides (X - H 1, F 2, Br 3, 14, OCH3 5) were synthesized and their solid state structures were probed by C-13 CP/MAS NMR spectroscopy. All disulfides adopt a layered conformation and both indole rings in one molecule were assumed to have very similar structural parameters, which is in agreement with a simple spectral pattern. For compounds I and 5 X-ray diffraction results are also presented. In the crystals of 1 and 5, the packing of the molecules is stabilized by dissimilar weak intermolecular interactions: in 1 dominate the N1-H1 center dot center dot center dot pi intermolecular hydrogen bonds and in 5 the C2-H2 center dot center dot center dot O10 intermolecular hydrogen bonds predominate. The di-5-fluoroindol-3-yl disulfide 2 and di-5-iodoindol-3-yl disulfide 4 were found to reduce considerably the growth of prostate cancer cell PC-3. (C) 2008 Elsevier B.V. All rights reserved.