(5S)-4-(tert-butoxy)-1-((3S)-1-(2-isobutyl-5-oxo-2,5-dihydro-1H-pyrrol-3-yl)pyrrolidin-3-yl)-5-methyl-1H-pyrrol-2(5H)-one | 1316848-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: (5S)-4-(tert-butoxy)-1-((3S)-1-(2-isobutyl-5-oxo-2,5-dihydro-1H-pyrrol-3-yl)pyrrolidin-3-yl)-5-methyl-1H-pyrrol-2(5H)-one
• 英文别名: (2S)-2-methyl-3-[(2-methylpropan-2-yl)oxy]-1-[(3S)-1-[(2S)-2-(2-methylpropyl)-5-oxo-1,2-dihydropyrrol-3-yl]pyrrolidin-3-yl]-2H-pyrrol-5-one
• CAS: 1316848-24-4
• 化学式: C₂₁H₃₃N₃O₃
• 分子量: 375.511
• InChiKey: WRONEIHTUKUXBU-JYJNAYRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  61.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S)-4-(tert-butoxy)-1-((3S)-1-(2-isobutyl-5-oxo-2,5-dihydro-1H-pyrrol-3-yl)pyrrolidin-3-yl)-5-methyl-1H-pyrrol-2(5H)-one 在 三氟乙酸 、 原甲酸三甲酯 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 17.0h， 生成 C₃₄H₅₁N₅O₅
  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：

  L-丙氨酸叔丁酯盐酸盐 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 sodium carbonate 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 氯仿 、 异丙醇 为溶剂， -78.0~75.0 ℃ 、101.33 kPa 条件下， 反应 20.17h， 生成 (5S)-4-(tert-butoxy)-1-((3S)-1-(2-isobutyl-5-oxo-2,5-dihydro-1H-pyrrol-3-yl)pyrrolidin-3-yl)-5-methyl-1H-pyrrol-2(5H)-one
  参考文献：
  名称：

  Pyrrolinone–Pyrrolidine Oligomers as Universal Peptidomimetics

  摘要：

  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.

  DOI：

  10.1021/ja2033734

文献信息

• 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.
• 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.