2-(2-氨基苯氧基乙胺基)甲酸叔丁酯 | 263410-16-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(2-氨基苯氧基乙胺基)甲酸叔丁酯
• 英文名称: tert-butyl (2-(2-aminophenoxy)ethyl)carbamate
• 英文别名: tert-butyl N-[2-(2-aminophenoxy)ethyl]carbamate
• CAS: 263410-16-8
• 化学式: C₁₃H₂₀N₂O₃
• 分子量: 252.313
• InChiKey: VCJINZUTBRZEQT-UHFFFAOYSA-N

物化性质

• 沸点：
  411.2±25.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  73.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-氨基苯氧基乙胺基)甲酸叔丁酯 在 盐酸 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  [EN] PYRAZOL-3-ONES THAT ACTIVATE PRO-APOPTOTIC BAX
  [FR] PYRAZOL-3-ONES QUI ACTIVENT LE BAX PRO-APOPTOTIQUE

  摘要：

  公开号：

  WO2013055949A3
• 作为产物：
  描述：

  tert-butyl (2-(2-nitrophenoxy)ethyl)carbamate 在 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 2-(2-氨基苯氧基乙胺基)甲酸叔丁酯
  参考文献：
  名称：

  Rational design of urea-based glutamate carboxypeptidase II (GCPII) inhibitors as versatile tools for specific drug targeting and delivery

  摘要：

  Glutamate carboxypeptidase II (GCPII), also known as prostate specific membrane antigen (PSMA), is an established prostate cancer marker and is considered a promising target for specific anticancer drug delivery. Low-molecular-weight inhibitors of GCPII are advantageous specific ligands for this purpose. However, they must be modified with a linker to enable connection of the ligand with an imaging molecule, anticancer drug, and/or nanocarrier. Here, we describe a structure-activity relationship (SAR) study of GCPII inhibitors with linkers suitable for imaging and drug delivery. Structure-assisted inhibitor design and targeting of a specific GCPII exosite resulted in a 7-fold improvement in Ki value compared to the parent structure. X-ray structural analysis of the inhibitor series led to the identification of several inhibitor binding modes. We also optimized the length of the inhibitor linker for effective attachment to a biotin-binding molecule and showed that the optimized inhibitor could be used to target nanoparticles to cells expressing GCPII.

  DOI：

  10.1016/j.bmc.2014.05.061

文献信息

• Rational design of urea-based glutamate carboxypeptidase II (GCPII) inhibitors as versatile tools for specific drug targeting and delivery
  作者：Jan Tykvart、Jiří Schimer、Jitka Bařinková、Petr Pachl、Lenka Poštová-Slavětínská、Pavel Majer、Jan Konvalinka、Pavel Šácha

  DOI：10.1016/j.bmc.2014.05.061

  日期：2014.8

  Glutamate carboxypeptidase II (GCPII), also known as prostate specific membrane antigen (PSMA), is an established prostate cancer marker and is considered a promising target for specific anticancer drug delivery. Low-molecular-weight inhibitors of GCPII are advantageous specific ligands for this purpose. However, they must be modified with a linker to enable connection of the ligand with an imaging molecule, anticancer drug, and/or nanocarrier. Here, we describe a structure-activity relationship (SAR) study of GCPII inhibitors with linkers suitable for imaging and drug delivery. Structure-assisted inhibitor design and targeting of a specific GCPII exosite resulted in a 7-fold improvement in Ki value compared to the parent structure. X-ray structural analysis of the inhibitor series led to the identification of several inhibitor binding modes. We also optimized the length of the inhibitor linker for effective attachment to a biotin-binding molecule and showed that the optimized inhibitor could be used to target nanoparticles to cells expressing GCPII.
• [EN] PYRAZOL-3-ONES THAT ACTIVATE PRO-APOPTOTIC BAX<br/>[FR] PYRAZOL-3-ONES QUI ACTIVENT LE BAX PRO-APOPTOTIQUE
  申请人：DANA FARBER CANCER INST INC

  公开号：WO2013055949A3

  公开（公告）日：2013-07-04