3β-(p-chlorophenyl)tropan-2β-carboxylic acid 2-(p-nitrophenyl)ethyl ester | 140695-33-6

• 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-(p-chlorophenyl)tropan-2β-carboxylic acid 2-(p-nitrophenyl)ethyl ester
• 英文别名: 2-(4-nitrophenyl)ethyl (1R,2S,3S,5S)-3-(4-chlorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• CAS: 140695-33-6
• 化学式: C₂₃H₂₅ClN₂O₄
• 分子量: 428.915
• InChiKey: NIAWVABUSUNUMW-CBPXPLCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  30
• 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：
  75.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3β-(p-chlorophenyl)tropan-2β-carboxylic acid 2-(p-nitrophenyl)ethyl ester 在 盐酸 、 nickel boride 、 一氯化碘 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 生成 3β-(p-chlorophenyl)tropan-2β-carboxylic acid 2-(3-iodo-4-aminophenyl)ethyl ester
  参考文献：
  名称：

  Probes for the cocaine receptor. Potentially irreversible ligands for the dopamine transporter

  摘要：

  Several potentially irreversible ligands (i.e., wash-resistant binding inhibitors) for the cocaine receptor site on the dopamine transporter, derived from (-)-cocaine or 3-beta-phenyltropan-2-beta-carboxylic acid methyl ester (WIN 35,065-2), were prepared and shown to produce wash-resistant inhibition of [H-3]-3-beta-(p-fluorophenyl)tropan-2-beta-carboxylic acid methyl ester ([H-3]WIN 35,428) binding. All the compounds prepared had the same absolute configuration as cocaine; they include analogues possessing chemically reactive groups such as the isothiocyanato and bromoacetamido as well as photoactive azido groups. The potentially irreversible ligands, as well as all the intermediates prepared in this study, were evaluated for their ability to inhibit the binding of [H-3]WIN 35,428 in coincubation experiments. Of the potentially irreversible ligands, 3-beta-(p-chlorophenyl)tropan-2-beta-carboxylic acid 2-[p-(bromoacetamido)phenyl]ethyl ester (6c) had the highest apparent potency. The potentially irreversible ligands were also preincubated, and inhibition of [H-3]WIN 35,428 binding was determined both before and after washing the ligand-exposed tissues. The most effective ligands in this regard were 3-beta-(3-iodo-4-azidophenyl)tropan-2-beta-carboxylic acid methyl ester (5) and 3-beta-(p-chlorophenyl)tropan-2-beta-carboxylic acid 2-(3-iodo-4-azidophenyl)ethyl ester (6d). The structure-activity relationships of these data are discussed.

  DOI：

  10.1021/jm00088a017
• 作为产物：
  描述：

  甲基(1R)-3-(4-氯苯基)-8-甲基-8-氮杂双环[3.2.1]辛烷-2-羧酸酯 在 吡啶 、 氯化亚砜 、 水 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 反应 78.0h， 生成 3β-(p-chlorophenyl)tropan-2β-carboxylic acid 2-(p-nitrophenyl)ethyl ester
  参考文献：
  名称：

  Probes for the cocaine receptor. Potentially irreversible ligands for the dopamine transporter

  摘要：

  Several potentially irreversible ligands (i.e., wash-resistant binding inhibitors) for the cocaine receptor site on the dopamine transporter, derived from (-)-cocaine or 3-beta-phenyltropan-2-beta-carboxylic acid methyl ester (WIN 35,065-2), were prepared and shown to produce wash-resistant inhibition of [H-3]-3-beta-(p-fluorophenyl)tropan-2-beta-carboxylic acid methyl ester ([H-3]WIN 35,428) binding. All the compounds prepared had the same absolute configuration as cocaine; they include analogues possessing chemically reactive groups such as the isothiocyanato and bromoacetamido as well as photoactive azido groups. The potentially irreversible ligands, as well as all the intermediates prepared in this study, were evaluated for their ability to inhibit the binding of [H-3]WIN 35,428 in coincubation experiments. Of the potentially irreversible ligands, 3-beta-(p-chlorophenyl)tropan-2-beta-carboxylic acid 2-[p-(bromoacetamido)phenyl]ethyl ester (6c) had the highest apparent potency. The potentially irreversible ligands were also preincubated, and inhibition of [H-3]WIN 35,428 binding was determined both before and after washing the ligand-exposed tissues. The most effective ligands in this regard were 3-beta-(3-iodo-4-azidophenyl)tropan-2-beta-carboxylic acid methyl ester (5) and 3-beta-(p-chlorophenyl)tropan-2-beta-carboxylic acid 2-(3-iodo-4-azidophenyl)ethyl ester (6d). The structure-activity relationships of these data are discussed.

  DOI：

  10.1021/jm00088a017

文献信息

• Probes for the cocaine receptor. Potentially irreversible ligands for the dopamine transporter
  作者：F. Ivy Carroll、Yigong Gao、Philip Abraham、Anita H. Lewin、Robert Lew、Amrat Patel、John W. Boja、Michael J. Kuhar

  DOI：10.1021/jm00088a017

  日期：1992.5

  Several potentially irreversible ligands (i.e., wash-resistant binding inhibitors) for the cocaine receptor site on the dopamine transporter, derived from (-)-cocaine or 3-beta-phenyltropan-2-beta-carboxylic acid methyl ester (WIN 35,065-2), were prepared and shown to produce wash-resistant inhibition of [H-3]-3-beta-(p-fluorophenyl)tropan-2-beta-carboxylic acid methyl ester ([H-3]WIN 35,428) binding. All the compounds prepared had the same absolute configuration as cocaine; they include analogues possessing chemically reactive groups such as the isothiocyanato and bromoacetamido as well as photoactive azido groups. The potentially irreversible ligands, as well as all the intermediates prepared in this study, were evaluated for their ability to inhibit the binding of [H-3]WIN 35,428 in coincubation experiments. Of the potentially irreversible ligands, 3-beta-(p-chlorophenyl)tropan-2-beta-carboxylic acid 2-[p-(bromoacetamido)phenyl]ethyl ester (6c) had the highest apparent potency. The potentially irreversible ligands were also preincubated, and inhibition of [H-3]WIN 35,428 binding was determined both before and after washing the ligand-exposed tissues. The most effective ligands in this regard were 3-beta-(3-iodo-4-azidophenyl)tropan-2-beta-carboxylic acid methyl ester (5) and 3-beta-(p-chlorophenyl)tropan-2-beta-carboxylic acid 2-(3-iodo-4-azidophenyl)ethyl ester (6d). The structure-activity relationships of these data are discussed.