methyl 2-amino-3-(7-methoxy-1H-indol-3-yl)propanoate | 355017-48-0

• 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: methyl 2-amino-3-(7-methoxy-1H-indol-3-yl)propanoate
• CAS: 355017-48-0
• 化学式: C₁₃H₁₆N₂O₃
• 分子量: 248.282
• InChiKey: PDGMDZRZEWHXQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  77.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-amino-3-(7-methoxy-1H-indol-3-yl)propanoate 、 异硫氰酸甲酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 5-(7-Methoxy-1H-indol-3-ylmethyl)-3-methyl-2-thioxo-imidazolidin-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-methoxy-1H-indol-3-yl)-N,N-dimethylmethanamine 在 盐酸 、 sodium hydroxide 、 氯化亚砜 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 methyl 2-amino-3-(7-methoxy-1H-indol-3-yl)propanoate
  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

• Amino acid derivatives and use thereof as nep, ace and ece inhibitors
  申请人：——

  公开号：US20030055086A1

  公开（公告）日：2003-03-20

  Compounds of formula (I): 1 wherein 0≦n≦3, 0≦m≦6, R 3 and R 4 together form a phenyl ring, B represents a heteroaryl group, R 1 and R 2 represent a hydrogen atom or groups as defined in the description.

  式(I)的化合物：其中0≤n≤3，0≤m≤6，R3和R4共同形成苯环，B代表杂环芳基基团，R1和R2代表氢原子或根据说明定义的基团。
• US6716852B2
  申请人：——

  公开号：US6716852B2

  公开（公告）日：2004-04-06
• 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.