5-(4-(2-azido-5-bromobenzyloxy)phenyl)dihydrofuran-2(3H)-one | 1245786-17-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(4-(2-azido-5-bromobenzyloxy)phenyl)dihydrofuran-2(3H)-one
• 英文别名: 5-[4-[(2-Azido-5-bromophenyl)methoxy]phenyl]oxolan-2-one
• CAS: 1245786-17-7
• 化学式: C₁₇H₁₄BrN₃O₃
• 分子量: 388.22
• InChiKey: IEIOIXZDECQKCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(4-(2-azido-5-bromobenzyloxy)phenyl)dihydrofuran-2(3H)-one 在 四(三苯基膦)钯 、 六正丁基二锡 作用下， 以 甲苯 为溶剂， 反应 14.0h， 生成 5-(4-(2-amino-5-bromobenzyloxy)phenyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Design, Synthesis, and in Vitro Pharmacology of New Radiolabeled γ-Hydroxybutyric Acid Analogues Including Photolabile Analogues with Irreversible Binding to the High-Affinity γ-Hydroxybutyric Acid Binding Sites

  摘要：

  gamma-Hydroxybutyric acid (GHB) is a psychotropic compound endogenous to the brain. Despite its potential physiological significance, the complete molecular mechanisms of action remain unexplained. To facilitate the isolation and identification of the high-affinity GHB binding site, we herein report the design and synthesis of the first I-125-labeled radioligands in the field, one of which contains a photoaffinity label which enables it to bind irreversibly to the high-affinity GHB binding sites.

  DOI：

  10.1021/jm1006325
• 作为产物：
  描述：

  5-(4-hydroxyphenyl)tetrahydrofuran-2-one 、 2-azido-5-bromobenzyl methanesulfonate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以70%的产率得到5-(4-(2-azido-5-bromobenzyloxy)phenyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Design, Synthesis, and in Vitro Pharmacology of New Radiolabeled γ-Hydroxybutyric Acid Analogues Including Photolabile Analogues with Irreversible Binding to the High-Affinity γ-Hydroxybutyric Acid Binding Sites

  摘要：

  gamma-Hydroxybutyric acid (GHB) is a psychotropic compound endogenous to the brain. Despite its potential physiological significance, the complete molecular mechanisms of action remain unexplained. To facilitate the isolation and identification of the high-affinity GHB binding site, we herein report the design and synthesis of the first I-125-labeled radioligands in the field, one of which contains a photoaffinity label which enables it to bind irreversibly to the high-affinity GHB binding sites.

  DOI：

  10.1021/jm1006325

文献信息

• Design, Synthesis, and in Vitro Pharmacology of New Radiolabeled γ-Hydroxybutyric Acid Analogues Including Photolabile Analogues with Irreversible Binding to the High-Affinity γ-Hydroxybutyric Acid Binding Sites
  作者：Paola Sabbatini、Petrine Wellendorph、Signe Høg、Martin H. F. Pedersen、Hans Bräuner-Osborne、Lars Martiny、Bente Frølund、Rasmus P. Clausen

  DOI：10.1021/jm1006325

  日期：2010.9.9

  gamma-Hydroxybutyric acid (GHB) is a psychotropic compound endogenous to the brain. Despite its potential physiological significance, the complete molecular mechanisms of action remain unexplained. To facilitate the isolation and identification of the high-affinity GHB binding site, we herein report the design and synthesis of the first I-125-labeled radioligands in the field, one of which contains a photoaffinity label which enables it to bind irreversibly to the high-affinity GHB binding sites.