2-Amino-3-(7-chloro-1-methyl-1H-indol-3-yl)-propionic acid methyl ester | 870481-83-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-Amino-3-(7-chloro-1-methyl-1H-indol-3-yl)-propionic acid methyl ester
• CAS: 870481-83-7
• 化学式: C₁₃H₁₅ClN₂O₂
• 分子量: 266.727
• InChiKey: YIEPXNFUORGMHN-UHFFFAOYSA-N

物化性质

• 沸点：
  411.7±40.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  57.25
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-Amino-3-(7-chloro-1-methyl-1H-indol-3-yl)-propionic acid methyl ester 、 异硫氰酸甲酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以98%的产率得到5-[(7-Chloro-1-methylindol-3-yl)methyl]-3-methyl-2-sulfanylideneimidazolidin-4-one
  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-氯吲哚 在 盐酸 、 氢氧化钾 、 sodium hydroxide 、 氯化亚砜 、 溶剂黄146 作用下， 以 四氢呋喃 、 二甲基亚砜 、 甲苯 为溶剂， 反应 166.0h， 生成 2-Amino-3-(7-chloro-1-methyl-1H-indol-3-yl)-propionic acid methyl ester
  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