{(2S,4R)-1-[4,4-Bis-(3-methyl-thiophen-2-yl)-but-3-enyl]-4-hydroxy-pyrrolidin-2-yl}-acetic acid | 850741-11-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: {(2S,4R)-1-[4,4-Bis-(3-methyl-thiophen-2-yl)-but-3-enyl]-4-hydroxy-pyrrolidin-2-yl}-acetic acid
• 英文别名: 2-((2S,4R)-1-(4,4-bis(3-methylthiophen-2-yl)but-3-enyl)-4-hydroxypyrrolidin-2-yl)acetic acid；2-[(2S,4R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl]-4-hydroxypyrrolidin-2-yl]acetic acid
• CAS: 850741-11-6
• 化学式: C₂₀H₂₅NO₃S₂
• 分子量: 391.555
• InChiKey: LJBQPELFQMHCCO-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  {(2S,4R)-1-[4,4-Bis-(3-methyl-thiophen-2-yl)-but-3-enyl]-4-hydroxy-pyrrolidin-2-yl}-acetic acid 在 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 29.0h， 生成 {(2S,4S)-1-[4,4-Bis-(3-methyl-thiophen-2-yl)-but-3-enyl]-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 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 草酰氯 、 氢气 、 silver(I) acetate 、 potassium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 197.5h， 生成 {(2S,4R)-1-[4,4-Bis-(3-methyl-thiophen-2-yl)-but-3-enyl]-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