tert-butyl 3-((2-ethoxy-2-oxoethyl)amino)piperidine-1-carboxylate | 1291543-77-5

• 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: tert-butyl 3-((2-ethoxy-2-oxoethyl)amino)piperidine-1-carboxylate
• 英文别名: Tert-butyl 3-[(2-ethoxy-2-oxoethyl)amino]piperidine-1-carboxylate
• CAS: 1291543-77-5
• 化学式: C₁₄H₂₆N₂O₄
• 分子量: 286.371
• InChiKey: QBMXYGAQLQDNPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-((2-ethoxy-2-oxoethyl)amino)piperidine-1-carboxylate 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.25h， 生成 (+)-ethyl 2-[(benzyloxycarbonyl)(1-(tert-butoxycarbonyl-L-leucinyl)-(S)-piperidin-3-yl)amino]acetate
  参考文献：
  名称：

  3-Aminopiperidine-Based Peptide Analogues as the First Selective Noncovalent Inhibitors of the Bacterial Cysteine Protease IdeS

  摘要：

  A series of eight peptides corresponding to the amino acid sequence of the hinge region of IgG and 17 newly synthesized peptide analogues containing a piperidine moiety as a replacement of a glycine residue were tested as potential inhibitors of the bacterial IgG degrading enzyme of Streptococcus pyogenes, IdeS. None of the peptides showed any inhibitory activity of IdeS, but several piperidine-based analogues were identified as inhibitors. Two different analysis methods were used: an SDS-PAGE based assay to detect IgG cleavage products and a surface plasmon resonance spectroscopy based assay to quantify the degree of inhibition. To investigate the selectivity of the inhibitors for IdeS, all compounds were screened against two other related cysteine proteases (SpeB and papain). The selectivity results show that larger analogues that are active inhibitors of IdeS are even more potent as inhibitors of papain, whereas smaller analogues that are active inhibitors of IdeS inhibit neither SpeB nor papain. Two compounds were identified that exhibit high selectivity against IdeS and will be used for further studies.

  DOI：

  10.1021/jm201517a
• 作为产物：
  描述：

  1-Boc-哌啶 在 lithium hydroxide monohydrate 、 iridium(lll) bis[2-(2,4-difluorophenyl)-5-methylpyridine-N,C₂₀]-4,40-di-tert-butyl-2,20-bipyridine hexafluorophosphate 、 四乙基对甲苯磺酸铵 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 20.0h， 生成 tert-butyl 3-((2-ethoxy-2-oxoethyl)amino)piperidine-1-carboxylate
  参考文献：
  名称：

  双环扭曲酰胺和苯胺的模块化合成

  摘要：

  由于氮孤对与相邻 π 系统的共轭扰动，桥接酰胺和苯胺显示出有趣的特性。基于环烯氨基甲酸酯的光催化加氢胺化和随后的环化，描述了一种包含扭曲酰胺或苯胺的二氮杂双环支架的收敛方法。合成的模块化性质允许改变“扭曲”程度，从而改变酰胺和苯胺的性质。

  DOI：

  10.1039/d3cc01470c

文献信息

• Design and synthesis of a fragment set based on twisted bicyclic lactams
  作者：Haitham Hassan、Stephen P. Marsden、Adam Nelson

  DOI：10.1016/j.bmc.2018.02.027

  日期：2018.7

  by flatter molecules, and their shape diversity does not reflect that of the fragments that are theoretically possible. The design and synthesis of a set of bridged fragments containing a bridgehead nitrogen is described. Many of these fragments contain twisted lactams whose modulated electronic properties may present unusual opportunities for interaction with target proteins. The demonstrated novelty

  当前的片段集倾向于由较平坦的分子控制，并且它们的形状多样性并不反映理论上可能的片段的多样性。描述了一组包含桥头氮的桥连片段的设计和合成。这些片段中许多都含有扭曲的内酰胺，其内在的电子特性调节可能会提供与靶蛋白相互作用的不寻常机会。这组22个片段的新颖性，三维性和分子特性可为基于片段的药物发现提供有价值且高度独特的起点。