methyl (2S,4R)-4-benzyloxy-1-benzyloxycarbonylpyrrolidine-2-acetate | 850741-24-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (2S,4R)-4-benzyloxy-1-benzyloxycarbonylpyrrolidine-2-acetate
• 英文别名: benzyl (2S,4R)-2-(2-methoxy-2-oxoethyl)-4-phenylmethoxypyrrolidine-1-carboxylate
• CAS: 850741-24-1
• 化学式: C₂₂H₂₅NO₅
• 分子量: 383.444
• InChiKey: FLUVSYHFSDGORQ-VQTJNVASSA-N

物化性质

• 沸点：
  503.1±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2S,4R)-4-benzyloxy-1-benzyloxycarbonylpyrrolidine-2-acetate 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 氢气 、 potassium carbonate 、 potassium iodide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 198.0h， 生成 [(2S,4R)-1-(3-Carbazol-9-yl-propyl)-4-hydroxy-pyrrolidin-2-yl]-acetic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of new GABA-uptake inhibitors derived from proline and from pyrrolidine-2-acetic acid

  摘要：

  Several synthetic approaches to N-alkylated derivatives of 4-hydroxypyrrolidine-2-carboxylic acid and 4-hydroxypyrrolidine-2-acetic acid are described. The final compounds have been evaluated as potential inhibitors of the GABA transport proteins GAT-I and GAT-3. The biological assays used were based on bovine material or porcine brain. As compared to the corresponding 4-unsubstituted compounds, the 4-hydroxypyrrolidine-2-carboxylic acid and 4-hydroxypyrrolidine-2-acetic acid derivatives showed a significant decrease in the inhibitory potency at both GAT-1 and GAT-3 with only four compounds having reasonable affinity to GAT-1 (IC50: 5.1, 6.6 and 9.4 mu M) or GAT-3 (IC50:19.9 mu M), respectively. The biological data of the 4-hydroxypyrrolidine-2-acetic acid derivatives indicates that (2S)-configuration at the C-2 position for potent inhibition of GAT-1 and (4R)-configuration at the C-4 position for potent inhibition of GAT-3 may be crucial. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.11.004
• 作为产物：
  描述：

  (2S,4R)-4-(benzyloxy)-1-((benzyloxy)carbonyl)pyrrolidine-2-carboxylic acid 在 草酰氯 、 silver(I) acetate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 methyl (2S,4R)-4-benzyloxy-1-benzyloxycarbonylpyrrolidine-2-acetate
  参考文献：
  名称：

  Synthesis and biological evaluation of new GABA-uptake inhibitors derived from proline and from pyrrolidine-2-acetic acid

  摘要：

  Several synthetic approaches to N-alkylated derivatives of 4-hydroxypyrrolidine-2-carboxylic acid and 4-hydroxypyrrolidine-2-acetic acid are described. The final compounds have been evaluated as potential inhibitors of the GABA transport proteins GAT-I and GAT-3. The biological assays used were based on bovine material or porcine brain. As compared to the corresponding 4-unsubstituted compounds, the 4-hydroxypyrrolidine-2-carboxylic acid and 4-hydroxypyrrolidine-2-acetic acid derivatives showed a significant decrease in the inhibitory potency at both GAT-1 and GAT-3 with only four compounds having reasonable affinity to GAT-1 (IC50: 5.1, 6.6 and 9.4 mu M) or GAT-3 (IC50:19.9 mu M), respectively. The biological data of the 4-hydroxypyrrolidine-2-acetic acid derivatives indicates that (2S)-configuration at the C-2 position for potent inhibition of GAT-1 and (4R)-configuration at the C-4 position for potent inhibition of GAT-3 may be crucial. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.11.004

文献信息

• Synthesis and biological evaluation of new GABA-uptake inhibitors derived from proline and from pyrrolidine-2-acetic acid
  作者：Xueqing Zhao、Cornelia E. Hoesl、Georg C. Hoefner、Klaus T. Wanner

  DOI：10.1016/j.ejmech.2004.11.004

  日期：2005.3

  Several synthetic approaches to N-alkylated derivatives of 4-hydroxypyrrolidine-2-carboxylic acid and 4-hydroxypyrrolidine-2-acetic acid are described. The final compounds have been evaluated as potential inhibitors of the GABA transport proteins GAT-I and GAT-3. The biological assays used were based on bovine material or porcine brain. As compared to the corresponding 4-unsubstituted compounds, the 4-hydroxypyrrolidine-2-carboxylic acid and 4-hydroxypyrrolidine-2-acetic acid derivatives showed a significant decrease in the inhibitory potency at both GAT-1 and GAT-3 with only four compounds having reasonable affinity to GAT-1 (IC50: 5.1, 6.6 and 9.4 mu M) or GAT-3 (IC50:19.9 mu M), respectively. The biological data of the 4-hydroxypyrrolidine-2-acetic acid derivatives indicates that (2S)-configuration at the C-2 position for potent inhibition of GAT-1 and (4R)-configuration at the C-4 position for potent inhibition of GAT-3 may be crucial. (c) 2005 Elsevier SAS. All rights reserved.