(2R)-2-amino-3-(7-chloro-1H-indol-3-yl)-N-methylpropanamide | 870481-89-3

• 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: (2R)-2-amino-3-(7-chloro-1H-indol-3-yl)-N-methylpropanamide
• CAS: 870481-89-3
• 化学式: C₁₂H₁₄ClN₃O
• 分子量: 251.716
• InChiKey: OTSZNVZGULSCPG-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  70.9
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R)-2-amino-3-(7-chloro-1H-indol-3-yl)-N-methylpropanamide 、 三光气 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以34%的产率得到(5R)-5-[(7-氯-1H-吲哚-3-基)甲基]-3-甲基-2,4-咪唑烷二酮
  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：

  7-氯-D-色氨酸 在 氯化亚砜 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (2R)-2-amino-3-(7-chloro-1H-indol-3-yl)-N-methylpropanamide
  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