(R)-(-)-di-tert-butyl 2-<(benzyloxy)methyl>cyclopropane-1,1-dicarboxylate | 149578-22-3

• 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: (R)-(-)-di-tert-butyl 2-<(benzyloxy)methyl>cyclopropane-1,1-dicarboxylate
• 英文别名: ditert-butyl (2R)-2-(phenylmethoxymethyl)cyclopropane-1,1-dicarboxylate
• CAS: 149578-22-3
• 化学式: C₂₁H₃₀O₅
• 分子量: 362.466
• InChiKey: VNHMPTAQNJQHCN-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-(-)-di-tert-butyl 2-<(benzyloxy)methyl>cyclopropane-1,1-dicarboxylate 在 palladium on activated charcoal ammonium hydroxide 、 氢气 、 对甲苯磺酸 作用下， 以 甲醇 、 氯仿 、 乙酸乙酯 为溶剂， 生成 (1R,2R)-(+)-tert-butyl 2-(acetoxymethyl)-1-carbamoylcyclopropane-1-carboxylate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 1-Amino-2-Phosphonomethylcyclopropanecarboxylic Acids, New Group III Metabotropic Glutamate Receptor Agonists

  摘要：

  Stereoisomers of 1-amino-2-phosphonomethylcyclopropanecarboxylic acid (APCPr), conformationally restricted analogues of L-AP4 (2-amino-4-phosphonobutyric acid), have been prepared and evaluated at recombinant group III metabotropic glutamate receptors. They activate these receptors over a broad range of potencies. The most potent isomer (1S,2R)-APCPr displays a similar pharmacological profile as that of L-AP4 (EC50 0.72, 1.95, > 500, 0.34 mu M at mGlu4, 6, 7, 8 receptors, respectively, and no effect at group I/II mGluRs). It was characterized on native receptors located in the basal ganglia (BG) where it induced a robust and reversible inhibition of synaptic transmission. It was tested in vivo in haloperidol-induced catalepsy, a model of Parkinsonian akinesia, by direct infusion in the globus pallidus of the BG. At a dose of 0.5 nmol/mu L, catalepsy was significantly antagonized. This study reveals that (1S,2R)-APCPr is a potent group III mGluR agonist and confirms that these receptors may be considered as a therapeutic target in the Parkinson's disease.

  DOI：

  10.1021/jm070262c
• 作为产物：
  描述：

  (R)-(+)-3-苄氧基-1,2-丙二醇 在 氯化亚砜 、 sodium hydride 作用下， 以 四氯化碳 、 乙二醇二甲醚 为溶剂， 反应 3.0h， 生成 (R)-(-)-di-tert-butyl 2-<(benzyloxy)methyl>cyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 1-Amino-2-Phosphonomethylcyclopropanecarboxylic Acids, New Group III Metabotropic Glutamate Receptor Agonists

  摘要：

  Stereoisomers of 1-amino-2-phosphonomethylcyclopropanecarboxylic acid (APCPr), conformationally restricted analogues of L-AP4 (2-amino-4-phosphonobutyric acid), have been prepared and evaluated at recombinant group III metabotropic glutamate receptors. They activate these receptors over a broad range of potencies. The most potent isomer (1S,2R)-APCPr displays a similar pharmacological profile as that of L-AP4 (EC50 0.72, 1.95, > 500, 0.34 mu M at mGlu4, 6, 7, 8 receptors, respectively, and no effect at group I/II mGluRs). It was characterized on native receptors located in the basal ganglia (BG) where it induced a robust and reversible inhibition of synaptic transmission. It was tested in vivo in haloperidol-induced catalepsy, a model of Parkinsonian akinesia, by direct infusion in the globus pallidus of the BG. At a dose of 0.5 nmol/mu L, catalepsy was significantly antagonized. This study reveals that (1S,2R)-APCPr is a potent group III mGluR agonist and confirms that these receptors may be considered as a therapeutic target in the Parkinson's disease.

  DOI：

  10.1021/jm070262c

文献信息

• SUBSTITUTED SPIROPYRIDO[1,2-a]PYRAZINE DERIVATIVE AND PHARMACEUTICAL USE OF SAME AS HIV INTEGRASE INHIBITOR
  申请人：JAPAN TOBACCO INC.

  公开号：US20140221378A1

  公开（公告）日：2014-08-07

  Provided is a substituted spiropyrido[1,2-a]pyrazine derivative or a pharmaceutically acceptable salt thereof, which is useful as an anti-HIV agent. The present invention relates to a compound represented by the following formula [I] or [II] or a pharmaceutically acceptable salt thereof: wherein each symbol is as defined in the specification.

  提供了一种替代的螺环吡啶并[1,2-a]吡嗪衍生物或其药用盐，其作为一种抗HIV药物。本发明涉及以下式[I]或[II]所表示的化合物或其药用盐： 其中每个符号如规范中定义的那样。
• Synthesis of a valuable cyclopropyl chiron for preparations of 2,3-methanoamino acids
  作者：Kevin Burgess、Kwok Kan Ho、Chun Yen Ke

  DOI：10.1021/jo00066a033

  日期：1993.7
• SUBSTITUTED SPIROPYRIDO[1,2-a]PYRAZINE DERIVATIVE AND MEDICINAL USE THEREOF AS HIV INTEGRASE INHIBITOR
  申请人：JAPAN TOBACCO INC.

  公开号：US20170044156A1

  公开（公告）日：2017-02-16

  Provided is a substituted spiropyrido[1,2-a]pyrazine derivative or a pharmaceutically acceptable salt thereof, which is useful as an anti-HIV agent. The present invention relates to a compound represented by the following formula [I] or [II] or a pharmaceutically acceptable salt thereof: wherein each symbol is as defined in the specification.
• Synthesis and Biological Evaluation of 1-Amino-2-Phosphonomethylcyclopropanecarboxylic Acids, New Group III Metabotropic Glutamate Receptor Agonists
  作者：Pauline Sibille、Sébastien Lopez、Isabelle Brabet、Ornella Valenti、Nadia Oueslati、Florence Gaven、Cyril Goudet、Hugues-Olivier Bertrand、Jacques Neyton、Michael J. Marino、Marianne Amalric、Jean-Philippe Pin、Francine C. Acher

  DOI：10.1021/jm070262c

  日期：2007.7.1

  Stereoisomers of 1-amino-2-phosphonomethylcyclopropanecarboxylic acid (APCPr), conformationally restricted analogues of L-AP4 (2-amino-4-phosphonobutyric acid), have been prepared and evaluated at recombinant group III metabotropic glutamate receptors. They activate these receptors over a broad range of potencies. The most potent isomer (1S,2R)-APCPr displays a similar pharmacological profile as that of L-AP4 (EC50 0.72, 1.95, > 500, 0.34 mu M at mGlu4, 6, 7, 8 receptors, respectively, and no effect at group I/II mGluRs). It was characterized on native receptors located in the basal ganglia (BG) where it induced a robust and reversible inhibition of synaptic transmission. It was tested in vivo in haloperidol-induced catalepsy, a model of Parkinsonian akinesia, by direct infusion in the globus pallidus of the BG. At a dose of 0.5 nmol/mu L, catalepsy was significantly antagonized. This study reveals that (1S,2R)-APCPr is a potent group III mGluR agonist and confirms that these receptors may be considered as a therapeutic target in the Parkinson's disease.