methyl (1S,2R)-2-{[(1R,5S/1S,5R)-3-(4-chlorophenyl)-8-azabicyclo[3.2.1]oct-2-en-8-yl]methyl}-1-phenylcyclopropanecarboxylate | 1295650-30-4

• 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: methyl (1S,2R)-2-{[(1R,5S/1S,5R)-3-(4-chlorophenyl)-8-azabicyclo[3.2.1]oct-2-en-8-yl]methyl}-1-phenylcyclopropanecarboxylate
• 英文别名: methyl (1S,2R)-2-[[3-(4-chlorophenyl)-8-azabicyclo[3.2.1]oct-2-en-8-yl]methyl]-1-phenylcyclopropane-1-carboxylate
• CAS: 1295650-30-4
• 化学式: C₂₅H₂₆ClNO₂
• 分子量: 407.94
• InChiKey: ZVHCIKGTRQHMOV-XSRURWLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (1S,2R)-2-{[(1R,5S/1S,5R)-3-(4-chlorophenyl)-8-azabicyclo[3.2.1]oct-2-en-8-yl]methyl}-1-phenylcyclopropanecarboxylate 、 草酸 以 乙醚 为溶剂， 生成 methyl (1S,2R)-2-{[(1R,5S/1S,5R)-3-(4-chlorophenyl)-8-azabicyclo[3.2.1]oct-2-en-8-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：

  tropinone 在 盐酸 、 正丁基锂 、 1-氯乙基氯甲酸酯 、 碳酸氢钠 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 57.92h， 生成 methyl (1S,2R)-2-{[(1R,5S/1S,5R)-3-(4-chlorophenyl)-8-azabicyclo[3.2.1]oct-2-en-8-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.