3-(7-Chloro-1H-indol-3-yl)-propionitrile | 870481-91-7

• 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: 3-(7-Chloro-1H-indol-3-yl)-propionitrile
• 英文别名: 3-(7-chloro-1H-indol-3-yl)propanenitrile
• CAS: 870481-91-7
• 化学式: C₁₁H₉ClN₂
• 分子量: 204.659
• InChiKey: ITNOOWSMOUHZBM-UHFFFAOYSA-N

物化性质

• 沸点：
  441.3±30.0 °C(Predicted)
• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  39.6
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(7-Chloro-1H-indol-3-yl)-propionitrile 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以51%的产率得到3-(7-chloro-1H-indol-3-yl)propanal
  参考文献：
  名称：

  [EN] INHIBITORS OF CELLULAR NECROSIS AND RELATED METHODS
  [FR] INHIBITEURS DE NÉCROSE CELLULAIRE ET PROCÉDÉS ASSOCIÉS

  摘要：

  提供具有以下结构（I）的化合物：或其药用盐、前药、立体异构体或互变异构体。还提供相关化合物、制备方法以及利用这些化合物治疗各种适应症的用途，包括治疗坏死细胞疾病和/或炎症。

  公开号：

  WO2016094846A1
• 作为产物：
  描述：

  7-chlorotryptophol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 3-(7-Chloro-1H-indol-3-yl)-propionitrile
  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

文献信息

• [EN] INHIBITORS OF CELLULAR NECROSIS AND RELATED METHODS<br/>[FR] INHIBITEURS DE NÉCROSE CELLULAIRE ET PROCÉDÉS ASSOCIÉS
  申请人：HARVARD COLLEGE

  公开号：WO2016094846A1

  公开（公告）日：2016-06-16

  A compound having the following structure (I): or a pharmaceutically acceptable salt, prodrug, stereoisomer or tautomer thereof, is provided. Related compounds, methods for preparation of the same and uses of the compounds for treatment of various indications, including treatment of necrotic cell diseases and/or inflammation, are also provided.

  提供具有以下结构（I）的化合物：或其药用盐、前药、立体异构体或互变异构体。还提供相关化合物、制备方法以及利用这些化合物治疗各种适应症的用途，包括治疗坏死细胞疾病和/或炎症。
• INHIBITORS OF CELLULAR NECROSIS AND RELATED METHODS
  申请人：President and Fellows of Harvard College

  公开号：US20160168128A1

  公开（公告）日：2016-06-16

  A compound having the following structure (I): or a pharmaceutically acceptable salt, prodrug, stereoisomer or tautomer thereof, is provided. Related compounds, methods for preparation of the same and uses of the compounds for treatment of various indications, including treatment of necrotic cell diseases and/or inflammation, are also provided.

  提供具有以下结构（I）的化合物或其药学上可接受的盐、前药、立体异构体或互变异构体。还提供相关化合物、其制备方法以及用于治疗各种症状，包括治疗坏死细胞疾病和/或炎症的化合物的用途。
• US9499521B2
  申请人：——

  公开号：US9499521B2

  公开（公告）日：2016-11-22
• US9944628B2
  申请人：——

  公开号：US9944628B2

  公开（公告）日：2018-04-17
• 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.