(S)-5-(2-(methylthio)ethyl)pyrrolidine-2,4-dione | 74031-34-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-5-(2-(methylthio)ethyl)pyrrolidine-2,4-dione
• 英文别名: (S)-5-(2-methylsulfanyl-ethyl)-pyrrolidine-2,4-dione；(5S)-5-(2-methylsulfanylethyl)pyrrolidine-2,4-dione
• CAS: 74031-34-8
• 化学式: C₇H₁₁NO₂S
• 分子量: 173.236
• InChiKey: TYKAIMOQQYKFKA-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-5-(2-(methylthio)ethyl)pyrrolidine-2,4-dione 、 (3aS)-5c-((1R,2E,4E)-5-chlorocarbonyl-1,3-dimethyl-penta-2,4-dienyl)-2c,6t,9a-trimethyl-8-oxo-(9at)-octahydro-3ar,7c-epioxido-furo[3,2-b]oxocine-3c-carboxylic acid methyl ester 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (3aS)-5c-{(1R,2E,4E)-6-hydroxy-1,3-dimethyl-6-[(3E,5S)-5-(2-methylsulfanyl-ethyl)-2,4-dioxo-pyrrolidin-3-ylidene]-hexa-2,4-dienyl}-2c,6t,9a-trimethyl-8-oxo-(9at)-octahydro-3ar,7c-epioxido-furo[3,2-b]oxocine-3c-carboxylic acid methyl ester
  参考文献：
  名称：

  Nakagawa,S. et al., Heterocycles, 1979, vol. 13, p. 477 - 495

  摘要：

  DOI：
• 作为产物：
  描述：

  Boc-L-蛋氨酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 (S)-5-(2-(methylthio)ethyl)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

• Extended Piperidine–Piperidinone Protein Interface Mimics
  作者：Dongyue Xin、Arjun Raghuraman、Kevin Burgess

  DOI：10.1021/acs.joc.5b00300

  日期：2015.5.1

  dichroism (CD) study. Thus, an estimate of 36 Å for the N-to-C distance of a typical conformation of the penta(piperidinone–piperidine) was made. CD spectra of four progressively longer oligomers allowed assignment of elipticity changes around 300 nm that can be attributed to increased conformational ordering of the longer oligomers in solution.

  极简主义的结构H和I被设计为蛋白质界面模拟物。这些化学型的特性是：（i）比常规肽更高的刚性；（ii）较不易产生疏水聚集效应的手性和非平面杂环骨架；以及（iii）具有与天然氨基酸相对应的各种侧链的制备潜力酸。然而，在低聚（吡咯烷酮-哌啶）的H中间体中，易合成差向异构体。确定了这种差向异构的起源，然后研究集中在寡聚（哌啶酮-哌啶）化合物Ⅰ上。模拟我是通过迭代耦合准备的。一个五（哌啶酮-哌啶）以此方式制备。对该五聚体的一系列较低的同系物进行了结晶和研究（单晶X射线），并将其中的四个用于圆二色性（CD）研究。因此，对五（哌啶酮-哌啶）典型构象的N-C距离进行了估计，结果约为36Å。四种逐渐变长的低聚物的CD光谱允许分配约300 nm的椭圆率变化，这可归因于溶液中较长的低聚物的构象排列增加。
• Pyrrolinone–Pyrrolidine Oligomers as Universal Peptidomimetics
  作者：Arjun Raghuraman、Eunhwa Ko、Lisa M. Perez、Thomas R. Ioerger、Kevin Burgess

  DOI：10.1021/ja2033734

  日期：2011.8.17

  Peptidomimetics 1-3 were prepared from amino acid-derived tetramic acids 7 as the key starting materials. Calculations show that preferred conformations of 1 can align their side-chain vectors with amino acids in common secondary structures more effectively than conformations of 3. A good fit was found for a preferred conformation of 2 (an extended derivative of 1) with a sheet/beta-turn/sheet motif.
• PEPTIDOMIMETIC COMPOUNDS AND RELATED METHODS
  申请人：Burgess Kevin

  公开号：US20130288331A1

  公开（公告）日：2013-10-31

  Provided herein are compounds and methods of using same for the perturbation and/or inhibition of protein-protein interactions. Also provided herein is a data mining method useful for the identification of protein-protein interactions that may be inhibited by these compounds.
• Expanding the Scope of Oligo-pyrrolinone–Pyrrolidines as Protein–Protein Interface Mimics
  作者：Arjun Raghuraman、Dongyue Xin、Lisa M. Perez、Kevin Burgess

  DOI：10.1021/jo400323k

  日期：2013.5.17

  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.
• Nakagawa,S. et al., Heterocycles, 1979, vol. 13, p. 477 - 495
  作者：Nakagawa,S. et al.

  DOI：——

  日期：——