(S)-1-{2-[Tris-(4-methoxy-phenyl)-methoxy]-ethyl}-pyrrolidine-2-carbaldehyde | 909031-81-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (S)-1-{2-[Tris-(4-methoxy-phenyl)-methoxy]-ethyl}-pyrrolidine-2-carbaldehyde
• CAS: 909031-81-8
• 化学式: C₂₉H₃₃NO₅
• 分子量: 475.585
• InChiKey: XIVIWGFYJUQSQD-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  35.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  57.23
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-1-{2-[Tris-(4-methoxy-phenyl)-methoxy]-ethyl}-pyrrolidine-2-carbaldehyde 在 sodium hydroxide 、 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 24.0h， 生成 (Z)-3-((S)-1-{2-[Tris-(4-methoxy-phenyl)-methoxy]-ethyl}-pyrrolidin-2-yl)-acrylic acid
  参考文献：
  名称：

  New highly potent GABA uptake inhibitors selective for GAT-1 and GAT-3 derived from (R)- and (S)-proline and homologous pyrrolidine-2-alkanoic acids

  摘要：

  We synthesized proline and pyrrolidine-2-alkanoic acid derivatives in their enantiomerically pure form and evaluated them for their affinity to the GABA transport proteins GAT-1 and GAT-3. Among the compounds presented herein, (R)-pyrrolidine-2-acetic acid (R)-4d substituted with a 2- [tris(4-methoxyphenyl)methoxy] ethyl residue at the nitrogen atom showed the highest affinity at GAT-3 (IC50 = 3.1 mu M) comparable with the well-known GAT-3 blocker (S)-SNAP-5114. Compound (R)-4d displayed excellent subtype selectivity for GAT-3 (GAT-3:GAT-1 = 20:1). (S)-2-pyrrolidineacetic acid derivatives (S)-4b provided with a 4,4-diphenylbut-3-en-1-yl moiety and (S)-4c substituted with a 4,4-[di(3-methylthiophen-2-yl)]phenylbut-3-en-l-yl residue at the nitrogen atom exhibited IC50 values of 0.396 mu M and 0.343 mu M at the GAT-1 protein, respectively. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.01.019
• 作为产物：
  描述：

  methyl (S)-1-{2-[tris(4-methoxyphenyl)methoxy]ethyl}pyrrolidine-2-carboxylate 在 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 2.0h， 生成 (S)-1-{2-[Tris-(4-methoxy-phenyl)-methoxy]-ethyl}-pyrrolidine-2-carbaldehyde
  参考文献：
  名称：

  New highly potent GABA uptake inhibitors selective for GAT-1 and GAT-3 derived from (R)- and (S)-proline and homologous pyrrolidine-2-alkanoic acids

  摘要：

  We synthesized proline and pyrrolidine-2-alkanoic acid derivatives in their enantiomerically pure form and evaluated them for their affinity to the GABA transport proteins GAT-1 and GAT-3. Among the compounds presented herein, (R)-pyrrolidine-2-acetic acid (R)-4d substituted with a 2- [tris(4-methoxyphenyl)methoxy] ethyl residue at the nitrogen atom showed the highest affinity at GAT-3 (IC50 = 3.1 mu M) comparable with the well-known GAT-3 blocker (S)-SNAP-5114. Compound (R)-4d displayed excellent subtype selectivity for GAT-3 (GAT-3:GAT-1 = 20:1). (S)-2-pyrrolidineacetic acid derivatives (S)-4b provided with a 4,4-diphenylbut-3-en-1-yl moiety and (S)-4c substituted with a 4,4-[di(3-methylthiophen-2-yl)]phenylbut-3-en-l-yl residue at the nitrogen atom exhibited IC50 values of 0.396 mu M and 0.343 mu M at the GAT-1 protein, respectively. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.01.019