3-[4-(4-nitrobenzyl)-1-piperazinyl]propyl-N,N-bis(4-fluorophenyl)amine | 815608-49-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-[4-(4-nitrobenzyl)-1-piperazinyl]propyl-N,N-bis(4-fluorophenyl)amine
• 英文别名: 4-fluoro-N-(4-fluorophenyl)-N-[3-[4-[(4-nitrophenyl)methyl]piperazin-1-yl]propyl]aniline
• CAS: 815608-49-2
• 化学式: C₂₆H₂₈F₂N₄O₂
• 分子量: 466.531
• InChiKey: MDVJTRKNAINMQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-[4-(4-nitrobenzyl)-1-piperazinyl]propyl-N,N-bis(4-fluorophenyl)amine 在 palladium on activated charcoal 氢气 、 一氯化碘 、 溶剂黄146 、 sodium nitrite 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、275.79 kPa 条件下， 反应 4.5h， 生成 {3-[4-(4-Azido-3-iodo-benzyl)-piperazin-1-yl]-propyl}-bis-(4-fluoro-phenyl)-amine
  参考文献：
  名称：

  Novel Azido and Isothiocyanato Analogues of [3-(4-Phenylalkylpiperazin-1-yl)propyl]bis(4-fluorophenyl)amines as Potential Irreversible Ligands for the Dopamine Transporter

  摘要：

  Potential irreversible ligands were prepared, based on a series of 3-(1-piperazinyl)propyl-N,N-bis(4-fluorophenyl)amines, as molecular probes for the dopamine transporter (DAT). Both azido and isothiocyanato-substituted phenylalkyl analogues were synthesized and evaluated for displacement of [H-3]WIN 35 428 in rat caudate putamen tissue. All of the analogues showed moderate binding potencies at the DAT. The azido analogue, 16b, was radiolodinated and used to photolabel human DAT-transfected HEK 293 cell membranes. [I-125] 16b irreversibly labeled an similar to80 kDa band corresponding to the DAT detected by sodium dodecyl sulfate-polyacrylamide gel electrophoresis. This radioligand provides a novel addition to the growing arsenal of structurally diverse irreversible ligands that are being used to identify binding domains on the DAT Characterizing points of attachment of these irreversible probes to the DAT protein will ultimately help elucidate the three-dimensional arrangement of the transmembrane domains, identify individual binding sites of the DAT inhibitors, and direct future drug design.

  DOI：

  10.1021/jm049670w
• 作为产物：
  描述：

  对硝基溴化苄 、 4-fluoro-N-(4-fluorophenyl)-N-[3-(piperazin-1-yl)propyl]aniline 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以89%的产率得到3-[4-(4-nitrobenzyl)-1-piperazinyl]propyl-N,N-bis(4-fluorophenyl)amine
  参考文献：
  名称：

  Novel Azido and Isothiocyanato Analogues of [3-(4-Phenylalkylpiperazin-1-yl)propyl]bis(4-fluorophenyl)amines as Potential Irreversible Ligands for the Dopamine Transporter

  摘要：

  Potential irreversible ligands were prepared, based on a series of 3-(1-piperazinyl)propyl-N,N-bis(4-fluorophenyl)amines, as molecular probes for the dopamine transporter (DAT). Both azido and isothiocyanato-substituted phenylalkyl analogues were synthesized and evaluated for displacement of [H-3]WIN 35 428 in rat caudate putamen tissue. All of the analogues showed moderate binding potencies at the DAT. The azido analogue, 16b, was radiolodinated and used to photolabel human DAT-transfected HEK 293 cell membranes. [I-125] 16b irreversibly labeled an similar to80 kDa band corresponding to the DAT detected by sodium dodecyl sulfate-polyacrylamide gel electrophoresis. This radioligand provides a novel addition to the growing arsenal of structurally diverse irreversible ligands that are being used to identify binding domains on the DAT Characterizing points of attachment of these irreversible probes to the DAT protein will ultimately help elucidate the three-dimensional arrangement of the transmembrane domains, identify individual binding sites of the DAT inhibitors, and direct future drug design.

  DOI：

  10.1021/jm049670w

文献信息

• Novel Azido and Isothiocyanato Analogues of [3-(4-Phenylalkylpiperazin-1-yl)propyl]bis(4-fluorophenyl)amines as Potential Irreversible Ligands for the Dopamine Transporter
  作者：Jianjing Cao、John R. Lever、Theresa Kopajtic、Jonathan L. Katz、Anh T. Pham、Muhsinah L. Holmes、Joseph B. Justice、Amy Hauck Newman

  DOI：10.1021/jm049670w

  日期：2004.12.1

  Potential irreversible ligands were prepared, based on a series of 3-(1-piperazinyl)propyl-N,N-bis(4-fluorophenyl)amines, as molecular probes for the dopamine transporter (DAT). Both azido and isothiocyanato-substituted phenylalkyl analogues were synthesized and evaluated for displacement of [H-3]WIN 35 428 in rat caudate putamen tissue. All of the analogues showed moderate binding potencies at the DAT. The azido analogue, 16b, was radiolodinated and used to photolabel human DAT-transfected HEK 293 cell membranes. [I-125] 16b irreversibly labeled an similar to80 kDa band corresponding to the DAT detected by sodium dodecyl sulfate-polyacrylamide gel electrophoresis. This radioligand provides a novel addition to the growing arsenal of structurally diverse irreversible ligands that are being used to identify binding domains on the DAT Characterizing points of attachment of these irreversible probes to the DAT protein will ultimately help elucidate the three-dimensional arrangement of the transmembrane domains, identify individual binding sites of the DAT inhibitors, and direct future drug design.