methyl 4-amino-1H-indole-3-carboxylate | 1149360-30-4

• 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: methyl 4-amino-1H-indole-3-carboxylate
• CAS: 1149360-30-4
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: VYKXNGQFGCGTJO-UHFFFAOYSA-N

物化性质

• 沸点：
  415.4±25.0 °C(Predicted)
• 密度：
  1.339±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  68.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-amino-1H-indole-3-carboxylate 在 三甲基铝 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 正己烷 、 甲苯 为溶剂， 反应 3.0h， 生成 4-(pyridin-4-ylmethylamino)-N-(3-(trifluoromethyl)phenyl)-1H-indole-3-carboxamide
  参考文献：
  名称：

  KDR inhibitor with the intramolecular non-bonded interaction: Conformation–activity relationships of novel indole-3-carboxamide derivatives

  摘要：

  We previously reported that compound 1, having a similar conformation to PTK787 (2) by forming a pseudo ring structure with an intramolecular non-bonded S-O interaction, exhibited a potent inhibitory activity against VEGFR2 tyrosine kinase (KDR).(1) Applying the ideas of pseudo ring formations, we have designed three types of novel indole carboxamide derivatives 5-7 with an intramolecular hydrogen bonding or non-bonded S-O interaction. We describe the design and synthesis of 5-7, and also discuss the relationships of their KDR inhibitory activity and conformations that were stabilized by their intramolecular non-bonded interactions. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.063
• 作为产物：
  描述：

  4-硝基-1H-吲哚-3-羧酸甲酯 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以65%的产率得到methyl 4-amino-1H-indole-3-carboxylate
  参考文献：
  名称：

  KDR inhibitor with the intramolecular non-bonded interaction: Conformation–activity relationships of novel indole-3-carboxamide derivatives

  摘要：

  We previously reported that compound 1, having a similar conformation to PTK787 (2) by forming a pseudo ring structure with an intramolecular non-bonded S-O interaction, exhibited a potent inhibitory activity against VEGFR2 tyrosine kinase (KDR).(1) Applying the ideas of pseudo ring formations, we have designed three types of novel indole carboxamide derivatives 5-7 with an intramolecular hydrogen bonding or non-bonded S-O interaction. We describe the design and synthesis of 5-7, and also discuss the relationships of their KDR inhibitory activity and conformations that were stabilized by their intramolecular non-bonded interactions. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.063