(2S,4R)-4-(2-Cyano-ethoxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester | 865353-18-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,4R)-4-(2-Cyano-ethoxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester
• CAS: 865353-18-0
• 化学式: C₁₆H₁₈N₂O₅
• 分子量: 318.329
• InChiKey: IMCMTLXDCVLCCD-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  99.86
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,4R)-4-(2-Cyano-ethoxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 、 potassium carbonate 、 cobalt(II) chloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 生成
  参考文献：
  名称：

  Cell Penetrating Agents Based on a Polyproline Helix Scaffold

  摘要：

  Cell penetrating agents were designed and synthesized that introduce cationic and hydrophobic moieties along the backbone of a polyproline helix (PPII) in an amphiphilic manner. The CD profile has the features that are expected for a PPII helix, demonstrating that the addition of these groups had little effect on the backbone structure. Dramatic increases in uptake were found with MCF-7 cells when up to six guanidinium groups were positioned on the polyproline helix, whereas only modest increases in cellular uptake were observed with the amine-containing polyproline compounds as compared to their flexible counterparts. Amphiphilicity played a key role in the enhanced cell translocation, as scrambled versions of the designed agents, with hydrophobic and cationic groups on all faces of the helix, were only as effective as their flexible peptide counterparts. Interestingly, the most potent agent, P11LRR, demonstrated almost an order of magnitude more efficient cellular uptake as compared to that of the well-studied Tat peptide, with minimal cytotoxicity.

  DOI：

  10.1021/ja052377g
• 作为产物：
  描述：

  丙烯腈 、 Cbz-L-羟脯氨酸 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 以80%的产率得到(2S,4R)-4-(2-Cyano-ethoxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester
  参考文献：
  名称：

  通过阳离子两亲性聚脯氨酸螺旋的N末端修饰靶向细胞内病原细菌。

  摘要：

  细胞内病原体可以在哺乳动物细胞中繁衍，并且是许多抗微生物剂不可及的。在这里，我们提出了一种简便的方法，可通过修饰N端的疏水部分来增强阳离子两亲性聚脯氨酸螺旋（CAPHs）的细胞渗透和抗菌性能。这些改变的CAPHs在巨噬细胞内显示出优异的细胞渗透性，在某些情况下，细胞毒性最小。此外，一种CAPH，Pentyl-P14对多种病原菌表现出优异的抗菌活性，并促进巨噬细胞内细胞内志贺氏菌的清除。

  DOI：

  10.1021/acs.joc.0c00871