(S)-5-((1H-indol-3-yl)methyl)pyrrolidine-2,4-dione | 1313355-00-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-5-((1H-indol-3-yl)methyl)pyrrolidine-2,4-dione
• 英文别名: (5S)-5-(1H-indol-3-ylmethyl)pyrrolidine-2,4-dione
• CAS: 1313355-00-8
• 化学式: C₁₃H₁₂N₂O₂
• 分子量: 228.25
• InChiKey: PAUJCAUJPFOOFS-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  62
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  、 (S)-5-((1H-indol-3-yl)methyl)pyrrolidine-2,4-dione 在 palladium 10% on activated carbon 、 氢气 、 原甲酸三甲酯 作用下， 以 异丙醇 为溶剂， 反应 5.0h， 以52%的产率得到
  参考文献：
  名称：

  Expanding the Scope of Oligo-pyrrolinone–Pyrrolidines as Protein–Protein Interface Mimics

  摘要：

  Oligo-pyrrolinone-pyrrolidines (generic structure 1) have the potential to interfere with protein-protein interactions (PPIs), but to reduce this to practice it is necessary to be able to synthesize these structures with a variety of different side chains corresponding to genetically encoded proteins. This paper describes expansion of the synthetic scope of 1, the difficulties encountered in this process, particularly issues with epimerization and slow coupling rates, and methods to overcome them. Finally, spectroscopic and physicochemical properties as well as proteolytic stabilities of molecules in this series were measured; these data highlight the suitability of oligo-pyrrolinone-pyrrolidines for the development of pharmacological probes or pharmaceutical leads.

  DOI：

  10.1021/jo400323k
• 作为产物：
  描述：

  [2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-2-hydroxy-1-(1H-indol-3-ylmethyl)-ethyl]-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (S)-5-((1H-indol-3-yl)methyl)pyrrolidine-2,4-dione
  参考文献：
  名称：

  Expanding the Scope of Oligo-pyrrolinone–Pyrrolidines as Protein–Protein Interface Mimics

  摘要：

  Oligo-pyrrolinone-pyrrolidines (generic structure 1) have the potential to interfere with protein-protein interactions (PPIs), but to reduce this to practice it is necessary to be able to synthesize these structures with a variety of different side chains corresponding to genetically encoded proteins. This paper describes expansion of the synthetic scope of 1, the difficulties encountered in this process, particularly issues with epimerization and slow coupling rates, and methods to overcome them. Finally, spectroscopic and physicochemical properties as well as proteolytic stabilities of molecules in this series were measured; these data highlight the suitability of oligo-pyrrolinone-pyrrolidines for the development of pharmacological probes or pharmaceutical leads.

  DOI：

  10.1021/jo400323k

文献信息

• Bioactivity and Mode of Action of Bacterial Tetramic Acids
  作者：Martin Klapper、André Paschold、Shuaibing Zhang、Christiane Weigel、Hans-Martin Dahse、Sebastian Götze、Simona Pace、Stefanie König、Zhigang Rao、Lisa Reimer、Oliver Werz、Pierre Stallforth

  DOI：10.1021/acschembio.9b00388

  日期：2019.8.16

  antibacterial, antiproliferative, and cytotoxic activities. The length of the alkyl side chain and the nature of the amino acid residues within the tetramic acid moiety strongly affected activity, in particular against mycobacteria. The mode of action was shown to correlate with the ability of pyreudiones to act as protonophores. Removal of the acidic proton by methylation of pyreudione A resulted in

  微生物产生的3-酰基四酸显示出多种生物活性。吡啶二酮是从假单胞菌属细菌中分离出来的这类新成员。在这里，我们进行了结构-活性关系研究，并确定了它们的作用方式。开发了一种有效的仿生合成法来合成吡啶酮二酮。测试了吡啶酮及其合成类似物的杀螨，抑菌，抗增殖和细胞毒性活性。烷基侧链的长度和四氨基酸部分内氨基酸残基的性质强烈影响了活性，特别是抗分枝杆菌的活性。已显示作用方式与吡啶二酮充当质子体的能力相关。