3β-(3,4-dichlorophenyl)-8-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)ethyl]-8-aza-bicyclo[3.2.1]octane-2β-carboxylic acid methyl ester | 872460-78-1

• 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: 3β-(3,4-dichlorophenyl)-8-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)ethyl]-8-aza-bicyclo[3.2.1]octane-2β-carboxylic acid methyl ester
• 英文别名: methyl (1R,2S,3S,5S)-3-(3,4-dichlorophenyl)-8-[2-(1,3-dioxoisoindol-2-yl)ethyl]-8-azabicyclo[3.2.1]octane-2-carboxylate
• CAS: 872460-78-1
• 化学式: C₂₅H₂₄Cl₂N₂O₄
• 分子量: 487.383
• InChiKey: PEOSKIBBHJPYSG-OZPQRRJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 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：
  66.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3β-(3,4-dichlorophenyl)-8-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)ethyl]-8-aza-bicyclo[3.2.1]octane-2β-carboxylic acid methyl ester 在 N,N-二异丙基乙胺 、 肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 JHC 1-064
  参考文献：
  名称：

  Rhodamine-Labeled 2β-Carbomethoxy-3β-(3,4-dichlorophenyl)tropane Analogues as High-Affinity Fluorescent Probes for the Dopamine Transporter

  摘要：

  Novel fluorescent ligands were synthesized to identify a high-affinity probe that would enable visualization of the dopamine transporter (DAT) in living cells. Fluorescent tags were extended from the N- or 2-position of 2 beta-carbomethoxy-3 beta-(3,4-dichlorophenyl)tropane, using an ethylamino linker. The resulting 2-substituted (5) and N-substituted (9) rhodamine-labeled ligands provided the highest DAT binding affinities expressed in COS-7 cells (K-i = 27 and 18 nM, respectively) in the series. Visualization of the DAT with 5 and 9 was demonstrated by confocal fluorescence laser scanning microscopy in stably transfected HEK293 cells.

  DOI：

  10.1021/jm050431y
• 作为产物：
  描述：

  dicholoropane 在 1-氯乙基氯甲酸酯 、 sodium carbonate 、 potassium carbonate 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 3β-(3,4-dichlorophenyl)-8-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)ethyl]-8-aza-bicyclo[3.2.1]octane-2β-carboxylic acid methyl ester
  参考文献：
  名称：

  Rhodamine-Labeled 2β-Carbomethoxy-3β-(3,4-dichlorophenyl)tropane Analogues as High-Affinity Fluorescent Probes for the Dopamine Transporter

  摘要：

  Novel fluorescent ligands were synthesized to identify a high-affinity probe that would enable visualization of the dopamine transporter (DAT) in living cells. Fluorescent tags were extended from the N- or 2-position of 2 beta-carbomethoxy-3 beta-(3,4-dichlorophenyl)tropane, using an ethylamino linker. The resulting 2-substituted (5) and N-substituted (9) rhodamine-labeled ligands provided the highest DAT binding affinities expressed in COS-7 cells (K-i = 27 and 18 nM, respectively) in the series. Visualization of the DAT with 5 and 9 was demonstrated by confocal fluorescence laser scanning microscopy in stably transfected HEK293 cells.

  DOI：

  10.1021/jm050431y

文献信息

• Rhodamine-Labeled 2β-Carbomethoxy-3β-(3,4-dichlorophenyl)tropane Analogues as High-Affinity Fluorescent Probes for the Dopamine Transporter
  作者：Joo Hwan Cha、Mu-Fa Zou、Erika M. Adkins、Søren G. F. Rasmussen、Claus Juul Loland、Bernhard Schoenenberger、Ulrik Gether、Amy Hauck Newman

  DOI：10.1021/jm050431y

  日期：2005.12.1

  Novel fluorescent ligands were synthesized to identify a high-affinity probe that would enable visualization of the dopamine transporter (DAT) in living cells. Fluorescent tags were extended from the N- or 2-position of 2 beta-carbomethoxy-3 beta-(3,4-dichlorophenyl)tropane, using an ethylamino linker. The resulting 2-substituted (5) and N-substituted (9) rhodamine-labeled ligands provided the highest DAT binding affinities expressed in COS-7 cells (K-i = 27 and 18 nM, respectively) in the series. Visualization of the DAT with 5 and 9 was demonstrated by confocal fluorescence laser scanning microscopy in stably transfected HEK293 cells.