3α-(4-iodophenyl)tropane-2β-carboxylic acid methyl ester | 184376-53-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: 3α-(4-iodophenyl)tropane-2β-carboxylic acid methyl ester
• 英文别名: Lzd6F45mkx；methyl (1R,2S,3R,5S)-3-(4-iodophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• CAS: 184376-53-2
• 化学式: C₁₆H₂₀INO₂
• 分子量: 385.245
• InChiKey: SIIICDNNMDMWCI-XQLPTFJDSA-N

物化性质

• 沸点：
  405.3±45.0 °C(Predicted)
• 密度：
  1.493±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  3α-(4-iodophenyl)tropane-2β-carboxylic acid methyl ester 在 四(三苯基膦)钯 溶剂黄146 、 锌 作用下， 以 甲苯 为溶剂， 生成 2β,3α-3-(4'-vinylphenyl)nortropane
  参考文献：
  名称：

  Synthesis and biological evaluation of 2β,3α-(substituted phenyl)nortropanes as potential norepinephrine transporter imaging agents

  摘要：

  A series of 2 beta,3 alpha-(substituted phenyl)nortropanes was synthesized and evaluated in vitro for human monoamine transporters. All compounds studied in this series exhibited nanomolar potency for the norepinephrine transporter (NET). Radiolabeling and nonhuman primate microPET brain imaging studies were performed with the most promising compound, [C-11]1, to determine its utility as a NET imaging agent. Despite high in vitro affinity for the human NET, the high uptake of [C-11]1 in the caudate and putamen excludes its use as an in vivo PET imaging agent for the NET. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.056
• 作为产物：
  描述：

  methyl (1RS-2-exo-3-exo)-8-methyl-3-phenyl-8-azabicyclo<3.2.1>octane-2-carboxylate 在 碘 、 silver trifluoromethanesulfonate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到3α-(4-iodophenyl)tropane-2β-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of 2β,3α-(substituted phenyl)nortropanes as potential norepinephrine transporter imaging agents

  摘要：

  A series of 2 beta,3 alpha-(substituted phenyl)nortropanes was synthesized and evaluated in vitro for human monoamine transporters. All compounds studied in this series exhibited nanomolar potency for the norepinephrine transporter (NET). Radiolabeling and nonhuman primate microPET brain imaging studies were performed with the most promising compound, [C-11]1, to determine its utility as a NET imaging agent. Despite high in vitro affinity for the human NET, the high uptake of [C-11]1 in the caudate and putamen excludes its use as an in vivo PET imaging agent for the NET. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.056

文献信息

• Dopamine transporter imaging ligand
  申请人：Research Triangle Institute

  公开号：US06358492B1

  公开（公告）日：2002-03-19

  The 3&agr; isomer of RTI-55, RTI-352, is an effective in vivo binding ligand that reflects greater selectivity for the dopamine transporter than is observed with RTI-55. In addition, there is also a more rapid achievement of apparent equilibrium in the striatal-to-cerebellar ratio (compared to RTI-55) as the ratio peaks at about 30 min and is maintained for about 20 min thereafter. Such apparent equilibrium is useful in developing an approach to measuring the number of dopamine transporters present in tissues. Moreover, these results indicate that the utilization of 3&agr; isomers of a variety of 3&bgr;-(substituted phenyl)tropanes will result in greater selectivity for dopamine transporters and a more rapid of achievement of apparent equilibrium.

  RTI-55的3α异构体RTI-352是一种有效的体内结合配体，反映出对多巴胺转运体的更大选择性，这种选择性比RTI-55观察到的要高。此外，与RTI-55相比，在纹状体与小脑比率中也更快地达到明显的平衡状态，比率在约30分钟时达到峰值，此后约维持20分钟。这种明显的平衡状态有助于开发一种测量组织中多巴胺转运体数量的方法。此外，这些结果表明，利用各种3β-(取代苯基)曲梯酮的3α异构体将导致更高的多巴胺转运体选择性和更快的明显平衡状态的实现。
• 3α-(4‘-Substituted phenyl)tropane- 2β-carboxylic Acid Methyl Esters:  Novel Ligands with High Affinity and Selectivity at the Dopamine Transporter
  作者：Christopher R. Holmquist、Kathryn I. Keverline-Frantz、Philip Abraham、John W. Boja、Michael J. Kuhar、F. Ivy Carroll

  DOI：10.1021/jm960515u

  日期：1996.1.1