ethyl (2SR,1'SR,2'RS,3'RS)-N-(tertbutoxycarbonyl)-2-(2'ethoxycarbonyl-3'-hydroxymethylcyclopropyl) glycinate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (2SR,1'SR,2'RS,3'RS)-N-(tertbutoxycarbonyl)-2-(2'ethoxycarbonyl-3'-hydroxymethylcyclopropyl) glycinate
• 英文别名: ethyl (1S,2R,3S)-2-[(1R)-2-ethoxy-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxoethyl]-3-(hydroxymethyl)cyclopropane-1-carboxylate
• 化学式: C₁₆H₂₇NO₇
• 分子量: 345.393
• InChiKey: WMZVNEVDZISIJS-IRCOFANPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl (2SR,1'SR,2'RS,3'RS)-N-(tertbutoxycarbonyl)-2-(2'ethoxycarbonyl-3'-hydroxymethylcyclopropyl) glycinate 在 jones reagent 作用下， 以 丙酮 为溶剂， 以97%的产率得到ethyl 3-tert-butoxycarbonyl-4-oxo-3-azabicyclo[3.1.0]hexane-2,6-dicarboxylate
  参考文献：
  名称：

  C3′-cis-Substituted carboxycyclopropyl glycines as metabotropic glutamate 2/3 receptor agonists: Synthesis and SAR studies

  摘要：

  The synthesis of a series of C3'-cis-substituted carboxycyclopropyl glycines bearing a wide variety of functional groups is described, and the structure-activity relationship for this series as agonists of group II metabotropic glutamate receptors is reported. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.036
• 作为产物：
  描述：

  ethyl 2-oxo-3-oxabicyclo[3.1.0]hexane-6-carboxylate 在 盐酸 、 aluminum oxide 、 二异丁基氢化铝 、 碳酸氢钠 、 氯化铵 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙腈 为溶剂， 反应 144.0h， 生成 ethyl (2SR,1'SR,2'RS,3'RS)-N-(tertbutoxycarbonyl)-2-(2'ethoxycarbonyl-3'-hydroxymethylcyclopropyl) glycinate
  参考文献：
  名称：

  (2S,1‘S,2‘R,3‘R)-2-(2‘-Carboxy-3‘-hydroxymethylcyclopropyl) Glycine Is a Highly Potent Group 2 and 3 Metabotropic Glutamate Receptor Agonist with Oral Activity

  摘要：

  The asymmetric synthesis and biological activity of (2S,1'S,2R,3R)-2-(2 -carboxy-3'-hydroxy-methylcyclopropyl) glycine ((+)-3) is described. This novel C-3' substituted carboxy cyclopropyl glycine is a highly potent group 2 and group 3 mGluR agonist that has proven to be orally active in both fear potentiated startle (animal model for anxiety) and PCP-induced motor activation (animal model for psychosis) assays in rats.

  DOI：

  10.1021/jm030967o

文献信息

• C3′-cis-Substituted carboxycyclopropyl glycines as metabotropic glutamate 2/3 receptor agonists: Synthesis and SAR studies
  作者：Rosario González、Iván Collado、Beatriz López de Uralde、Alicia Marcos、Luisa M. Martín-Cabrejas、Concepción Pedregal、Jaime Blanco-Urgoiti、Javier Pérez-Castells、M. Alejandro Fernández、Sherri L. Andis、Bryan G. Johnson、Rebecca A. Wright、Darryle D. Schoepp、James A. Monn

  DOI：10.1016/j.bmc.2005.07.036

  日期：2005.12

  The synthesis of a series of C3'-cis-substituted carboxycyclopropyl glycines bearing a wide variety of functional groups is described, and the structure-activity relationship for this series as agonists of group II metabotropic glutamate receptors is reported. (c) 2005 Elsevier Ltd. All rights reserved.
• (2<i>S</i>,1‘<i>S</i>,2‘<i>R</i>,3‘<i>R</i>)-2-(2‘-Carboxy-3‘-hydroxymethylcyclopropyl) Glycine Is a Highly Potent Group 2 and 3 Metabotropic Glutamate Receptor Agonist with Oral Activity
  作者：Iván Collado、Concepción Pedregal、Ana Belén Bueno、Alicia Marcos、Rosario González、Jaime Blanco-Urgoiti、Javier Pérez-Castells、Darryle D. Schoepp、Rebecca A. Wright、Bryan G. Johnson、Ann E. Kingston、Eric D. Moher、David W. Hoard、Kelly I. Griffey、Joseph P. Tizzano

  DOI：10.1021/jm030967o

  日期：2004.1.1

  The asymmetric synthesis and biological activity of (2S,1'S,2R,3R)-2-(2 -carboxy-3'-hydroxy-methylcyclopropyl) glycine ((+)-3) is described. This novel C-3' substituted carboxy cyclopropyl glycine is a highly potent group 2 and group 3 mGluR agonist that has proven to be orally active in both fear potentiated startle (animal model for anxiety) and PCP-induced motor activation (animal model for psychosis) assays in rats.