3-[(5,6-dimethoxy-1H-indole-2-carbonyl)amino]propionic acid ethyl ester | 1092796-32-1

• 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-[(5,6-dimethoxy-1H-indole-2-carbonyl)amino]propionic acid ethyl ester
• 英文别名: ethyl 3-[(5,6-dimethoxy-1H-indole-2-carbonyl)amino]propanoate
• CAS: 1092796-32-1
• 化学式: C₁₆H₂₀N₂O₅
• 分子量: 320.345
• InChiKey: NGISXNPWCCPBCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[(5,6-dimethoxy-1H-indole-2-carbonyl)amino]propionic acid ethyl ester 在 lithium hydroxide monohydrate 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以89%的产率得到3-[(5,6-dimethoxy-1H-indole-2-carbonyl)amino]propionic acid
  参考文献：
  名称：

  Synthesis, Modeling, and RET Protein Kinase Inhibitory Activity of 3- and 4-Substituted β-Carbolin-1-ones

  摘要：

  A series of beta-carbolin-2-ones and 3,10-dihydro-2H-azepino[3,4-b]indol-1-ones have been designed, synthesized, and evaluated as RET protein kinase inhibitors oil the basis Of their Structural similarity with the prototype indolin-2-one RPI-1. Some beta-carbolin-2-ones (structure 2) showed ail ability to inhibit RET enzymatic activity in vitro and proliferation of RETC634R oncogene-transformed NIH3T3 cells comparable to that of the reference compound. The docking analysis of the interaction of these compounds with the crystallographic structure of RET tyrosine kinase domain suggested a new binding interaction scheme different from the one proposed during their design. The rigid structure of the compounds of this series represents a new scaffold with potential advantages in the design of RET protein kinase inhibitors.

  DOI：

  10.1021/jm8007823
• 作为产物：
  描述：

  5,6-二甲氧基吲哚-2-甲酸 、 beta-丙氨酸乙酯盐酸盐 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以96%的产率得到3-[(5,6-dimethoxy-1H-indole-2-carbonyl)amino]propionic acid ethyl ester
  参考文献：
  名称：

  Synthesis, Modeling, and RET Protein Kinase Inhibitory Activity of 3- and 4-Substituted β-Carbolin-1-ones

  摘要：

  A series of beta-carbolin-2-ones and 3,10-dihydro-2H-azepino[3,4-b]indol-1-ones have been designed, synthesized, and evaluated as RET protein kinase inhibitors oil the basis Of their Structural similarity with the prototype indolin-2-one RPI-1. Some beta-carbolin-2-ones (structure 2) showed ail ability to inhibit RET enzymatic activity in vitro and proliferation of RETC634R oncogene-transformed NIH3T3 cells comparable to that of the reference compound. The docking analysis of the interaction of these compounds with the crystallographic structure of RET tyrosine kinase domain suggested a new binding interaction scheme different from the one proposed during their design. The rigid structure of the compounds of this series represents a new scaffold with potential advantages in the design of RET protein kinase inhibitors.

  DOI：

  10.1021/jm8007823

文献信息

• Synthesis, Modeling, and RET Protein Kinase Inhibitory Activity of 3- and 4-Substituted β-Carbolin-1-ones
  作者：Raffaella Cincinelli、Giuliana Cassinelli、Sabrina Dallavalle、Cinzia Lanzi、Lucio Merlini、Maurizio Botta、Tiziano Tuccinardi、Adriano Martinelli、Sergio Penco、Franco Zunino

  DOI：10.1021/jm8007823

  日期：2008.12.25

  A series of beta-carbolin-2-ones and 3,10-dihydro-2H-azepino[3,4-b]indol-1-ones have been designed, synthesized, and evaluated as RET protein kinase inhibitors oil the basis Of their Structural similarity with the prototype indolin-2-one RPI-1. Some beta-carbolin-2-ones (structure 2) showed ail ability to inhibit RET enzymatic activity in vitro and proliferation of RETC634R oncogene-transformed NIH3T3 cells comparable to that of the reference compound. The docking analysis of the interaction of these compounds with the crystallographic structure of RET tyrosine kinase domain suggested a new binding interaction scheme different from the one proposed during their design. The rigid structure of the compounds of this series represents a new scaffold with potential advantages in the design of RET protein kinase inhibitors.