(2R)-2-[(2S,5S)-2,5-di(phenethyl)tetrahydro-1H-pyrrol-1-yl]-2-phenylethanol | 1187437-32-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2R)-2-[(2S,5S)-2,5-di(phenethyl)tetrahydro-1H-pyrrol-1-yl]-2-phenylethanol
• 英文别名: (2R)-2-[(2S,5S)-2,5-bis(2-phenylethyl)pyrrolidin-1-yl]-2-phenylethanol;hydrochloride
• CAS: 1187437-32-6
• 化学式: C₂₈H₃₃NO*ClH
• 分子量: 436.037
• InChiKey: NQLGNSAPLRENAM-JAQKLANPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.24
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  23.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R)-2-[(2S,5S)-2,5-di(phenethyl)tetrahydro-1H-pyrrol-1-yl]-2-phenylethanol 在 Pearlman's catalist 、 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以73%的产率得到(2S,5S)-2,5-diphenethylpyrrolidine hydrochloride
  参考文献：
  名称：

  Pyrrolidine Analogues of Lobelane: Relationship of Affinity for the Dihydrotetrabenazine Binding Site with Function of the Vesicular Monoamine Transporter 2 (VMAT2)

  摘要：

  Ring size reduction of the central piperidine ring of lobelane yielded pyrrolidine analogues that showed marked inconsistencies in their ability to bind to the dihydrotetrabenazine (DTBZ) binding site on the vesicular mono-amine transporter-2 (VMAT2) and their ability to inhibit VMAT2 function. The structure-activity relationships indicate that structural modification within the pyrrolidine series resulted in analogues that interact with two different sites, i.e., the DTBZ binding site and all alternative site on VMAT2 to inhibit transporter function.

  DOI：

  10.1021/jm900770h
• 作为产物：
  描述：

  在 盐酸 作用下， 以 乙醚 为溶剂， 生成 (2R)-2-[(2S,5S)-2,5-di(phenethyl)tetrahydro-1H-pyrrol-1-yl]-2-phenylethanol 、 (2R)-2-[(2S,5R)-2,5-di(phenethyl)tetrahydro-1H-pyrrol-1-yl]-2-phenylethanol
  参考文献：
  名称：

  Pyrrolidine Analogues of Lobelane: Relationship of Affinity for the Dihydrotetrabenazine Binding Site with Function of the Vesicular Monoamine Transporter 2 (VMAT2)

  摘要：

  Ring size reduction of the central piperidine ring of lobelane yielded pyrrolidine analogues that showed marked inconsistencies in their ability to bind to the dihydrotetrabenazine (DTBZ) binding site on the vesicular mono-amine transporter-2 (VMAT2) and their ability to inhibit VMAT2 function. The structure-activity relationships indicate that structural modification within the pyrrolidine series resulted in analogues that interact with two different sites, i.e., the DTBZ binding site and all alternative site on VMAT2 to inhibit transporter function.

  DOI：

  10.1021/jm900770h

文献信息

• Pyrrolidine Analogues of Lobelane: Relationship of Affinity for the Dihydrotetrabenazine Binding Site with Function of the Vesicular Monoamine Transporter 2 (VMAT2)
  作者：Ashish P. Vartak、Justin R. Nickell、Jaturaporn Chagkutip、Linda P. Dwoskin、Peter A. Crooks

  DOI：10.1021/jm900770h

  日期：2009.12.10

  Ring size reduction of the central piperidine ring of lobelane yielded pyrrolidine analogues that showed marked inconsistencies in their ability to bind to the dihydrotetrabenazine (DTBZ) binding site on the vesicular mono-amine transporter-2 (VMAT2) and their ability to inhibit VMAT2 function. The structure-activity relationships indicate that structural modification within the pyrrolidine series resulted in analogues that interact with two different sites, i.e., the DTBZ binding site and all alternative site on VMAT2 to inhibit transporter function.