1-(1H-indol-3-yl)cyclobutane-1-carbonitrile | 218772-65-7

• 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: 1-(1H-indol-3-yl)cyclobutane-1-carbonitrile
• CAS: 218772-65-7
• 化学式: C₁₃H₁₂N₂
• 分子量: 196.252
• InChiKey: OVRVFNIHDSNYQN-UHFFFAOYSA-N

物化性质

• 沸点：
  428.8±28.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  39.58
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(1H-indol-3-yl)cyclobutane-1-carbonitrile 在 二异丁基氢化铝 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 生成 5-[1-(1H-indol-3-yl)cyclobutyl]imidazolidine-2,4-dione
  参考文献：
  名称：

  Structure–activity relationship study of novel necroptosis inhibitors

  摘要：

  Necroptosis is a regulated caspase-independent cell death mechanism that results in morphological features resembling necrosis. It can be induced in a FADD-deficient variant of human Jurkat T cells treated with TNF-alpha. 5-(1H-Indol-3-ylmethyl)-2-thiohydantoins and 5-(1H-indol-3-ylmethyl)hydantoins were found to be potent necroptosis inhibitors (called necrostatins). A SAR study revealed that several positions of the indole were intolerant of substitution, while small substituents at the 7-position resulted in increased inhibitory activity. The hydantoin ring was also quite sensitive to structural modifications. A representative member of this compound class demonstrated moderate pharmacokinetic characteristics and readily entered the central nervous system upon intravenous administration. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.077
• 作为产物：
  描述：

  吲哚-3-乙腈 在 甲醇 、 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 1-(1H-indol-3-yl)cyclobutane-1-carbonitrile
  参考文献：
  名称：

  Conformationally constrained amino-acids: Synthesis of novel β, β-, 2,3-, and 3,4-cyclised tryptophans

  摘要：

  The synthesis of novel conformationally constrained tryptophan mimetics is described. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01920-0

文献信息

• Structure–activity relationship study of novel necroptosis inhibitors
  作者：Xin Teng、Alexei Degterev、Prakash Jagtap、Xuechao Xing、Sungwoon Choi、Régine Denu、Junying Yuan、Gregory D. Cuny

  DOI：10.1016/j.bmcl.2005.07.077

  日期：2005.11

  Necroptosis is a regulated caspase-independent cell death mechanism that results in morphological features resembling necrosis. It can be induced in a FADD-deficient variant of human Jurkat T cells treated with TNF-alpha. 5-(1H-Indol-3-ylmethyl)-2-thiohydantoins and 5-(1H-indol-3-ylmethyl)hydantoins were found to be potent necroptosis inhibitors (called necrostatins). A SAR study revealed that several positions of the indole were intolerant of substitution, while small substituents at the 7-position resulted in increased inhibitory activity. The hydantoin ring was also quite sensitive to structural modifications. A representative member of this compound class demonstrated moderate pharmacokinetic characteristics and readily entered the central nervous system upon intravenous administration. (c) 2005 Elsevier Ltd. All rights reserved.
• Conformationally constrained amino-acids: Synthesis of novel β, β-, 2,3-, and 3,4-cyclised tryptophans
  作者：David C. Horwell、Mary J. McKiernan、Simon Osborne

  DOI：10.1016/s0040-4039(98)01920-0

  日期：1998.11

  The synthesis of novel conformationally constrained tryptophan mimetics is described. (C) 1998 Elsevier Science Ltd. All rights reserved.