ethyl 2-((2S,3R,4S)-3-acetoxy-4-(benzoylamino)-1-benzoyl-6-((2-methoxyethoxy)methoxy)-1,2,3,4-tetrahydroquinolin-2-yl)acetate | 1068149-63-2

• 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: ethyl 2-((2S,3R,4S)-3-acetoxy-4-(benzoylamino)-1-benzoyl-6-((2-methoxyethoxy)methoxy)-1,2,3,4-tetrahydroquinolin-2-yl)acetate
• CAS: 1068149-63-2
• 化学式: C₃₃H₃₆N₂O₉
• 分子量: 604.657
• InChiKey: FDXFTTYOFDWWLS-ASVWTAOFSA-N

物化性质

• 沸点：
  763.8±60.0 °C(predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  44.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  129.7
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-((2S,3R,4S)-3-acetoxy-4-(benzoylamino)-1-benzoyl-6-((2-methoxyethoxy)methoxy)-1,2,3,4-tetrahydroquinolin-2-yl)acetate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.33h， 以93%的产率得到2-((2S,3R,4S)-4-benzamido-1-benzoyl-3-hydroxy-6-((2-methoxyethoxy)methoxy)-1,2,3,4-tetrahydroquinolin-2-yl)acetic acid
  参考文献：
  名称：

  The discovery of small molecule chemical probes of Bcl-XL and Mcl-1

  摘要：

  A tetrahydroaminoquinoline-based library was generated with the goals of finding small molecule modulators of protein-protein interactions. Several library members as well as other related intermediates were tested for their ability to bind to Bcl-X(L) and Mcl-1 by in silico and (15)N NMR studies. The NMR study led to the identification of the tetrahydroaminoquinoline-based nude scaffold, 7 as a weak binder (K(d) = 200 mu M for Bcl-X(L) and K(d) = 300 mu M for Mcl-1) to both proteins. Using this scaffold as the starting material, we then synthesized a focused library of only 9 derivatives by applying the principles of a fragment-based approach. All these derivatives were then tested by NMR and this led to the discovery of a novel, small molecule (MIPRALDEN, 17) as a binder to Mcl-1 and Bcl-XL (K(D) = 25 and 70 mu M). This finding is novel because to our knowledge there are not many small molecules known in the literature that bind to Mcl-1. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.023
• 作为产物：
  描述：

  ethyl 2-((2S,3S,4S)-3-acetoxy-4-(N-(allyloxycarbonyl)benzoylamino)-1-benzoyl-6-((2-methoxyethoxy)methoxy)-1,2,3,4-tetrahydroquinolin-2-yl)acetate 在 四(三苯基膦)钯 吗啉 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以89%的产率得到ethyl 2-((2S,3R,4S)-3-acetoxy-4-(benzoylamino)-1-benzoyl-6-((2-methoxyethoxy)methoxy)-1,2,3,4-tetrahydroquinolin-2-yl)acetate
  参考文献：
  名称：

  The discovery of small molecule chemical probes of Bcl-XL and Mcl-1

  摘要：

  A tetrahydroaminoquinoline-based library was generated with the goals of finding small molecule modulators of protein-protein interactions. Several library members as well as other related intermediates were tested for their ability to bind to Bcl-X(L) and Mcl-1 by in silico and (15)N NMR studies. The NMR study led to the identification of the tetrahydroaminoquinoline-based nude scaffold, 7 as a weak binder (K(d) = 200 mu M for Bcl-X(L) and K(d) = 300 mu M for Mcl-1) to both proteins. Using this scaffold as the starting material, we then synthesized a focused library of only 9 derivatives by applying the principles of a fragment-based approach. All these derivatives were then tested by NMR and this led to the discovery of a novel, small molecule (MIPRALDEN, 17) as a binder to Mcl-1 and Bcl-XL (K(D) = 25 and 70 mu M). This finding is novel because to our knowledge there are not many small molecules known in the literature that bind to Mcl-1. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.023