(+)-methyl (1R,2S)-2-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-1-phenylcyclopropanecarboxylate | 1295650-26-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (+)-methyl (1R,2S)-2-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-1-phenylcyclopropanecarboxylate
• 英文别名: (+)-Methyl(1R,2S)-2-[(4-Hydroxy-4-phenylpiperidin-1-yl)-methyl]-1-phenylcyclopropanecarboxylate；methyl (1R,2S)-2-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-1-phenylcyclopropane-1-carboxylate
• CAS: 1295650-26-8
• 化学式: C₂₃H₂₇NO₃
• 分子量: 365.472
• InChiKey: UNOGZCNQPVUIQG-OFNKIYASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-methyl (1R,2S)-2-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-1-phenylcyclopropanecarboxylate 、 草酸 以 乙醚 为溶剂， 生成 (+)-methyl (1R,2S)-2-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-1-phenylcyclopropanecarboxylate oxalate
  参考文献：
  名称：

  Novel Potent and Selective σ Ligands: Evaluation of Their Agonist and Antagonist Properties

  摘要：

  Novel enantiomers and diastereoisomers structurally related to sigma ligand (+)-MR200 were synthesized to improve sigma(1)/sigma(2) subtype selectivity. The selective sigma(1) ligand (-)-8 showed an antagonist profile determined by phenytoin differential modulation of binding affinity in vitro, confirmed in vivo by an increase of kappa opioid analgesia. The sigma(2) ligand (-)-9 displayed agonist properties in an in vitro isolated organ bath assay and antiproliferative effects on LNCaP and PC3 prostate cancer cell lines.

  DOI：

  10.1021/jm200144j
• 作为产物：
  描述：

  4-苯基-4-羟基哌啶 、 (+/-)-methyl cis-2-(bromomethyl)-1-phenylcyclopropanecarboxylate 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以355 mg的产率得到(+)-methyl (1R,2S)-2-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]-1-phenylcyclopropanecarboxylate
  参考文献：
  名称：

  Novel Potent and Selective σ Ligands: Evaluation of Their Agonist and Antagonist Properties

  摘要：

  Novel enantiomers and diastereoisomers structurally related to sigma ligand (+)-MR200 were synthesized to improve sigma(1)/sigma(2) subtype selectivity. The selective sigma(1) ligand (-)-8 showed an antagonist profile determined by phenytoin differential modulation of binding affinity in vitro, confirmed in vivo by an increase of kappa opioid analgesia. The sigma(2) ligand (-)-9 displayed agonist properties in an in vitro isolated organ bath assay and antiproliferative effects on LNCaP and PC3 prostate cancer cell lines.

  DOI：

  10.1021/jm200144j

文献信息

• Novel Potent and Selective σ Ligands: Evaluation of Their Agonist and Antagonist Properties
  作者：Agostino Marrazzo、Enrique J. Cobos、Carmela Parenti、Giuseppina Aricò、Giuseppina Marrazzo、Simone Ronsisvalle、Lorella Pasquinucci、Orazio Prezzavento、Nicola A. Colabufo、Marialessandra Contino、Luis G. González、Giovanna M. Scoto、Giuseppe Ronsisvalle

  DOI：10.1021/jm200144j

  日期：2011.5.26

  Novel enantiomers and diastereoisomers structurally related to sigma ligand (+)-MR200 were synthesized to improve sigma(1)/sigma(2) subtype selectivity. The selective sigma(1) ligand (-)-8 showed an antagonist profile determined by phenytoin differential modulation of binding affinity in vitro, confirmed in vivo by an increase of kappa opioid analgesia. The sigma(2) ligand (-)-9 displayed agonist properties in an in vitro isolated organ bath assay and antiproliferative effects on LNCaP and PC3 prostate cancer cell lines.