N-(2-{[N6-[(benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-L-lysyl]amino}ethyl)-N2-(tert-butoxycarbonyl)-L-tryptophanamide | 1186090-20-9

• 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: N-(2-{[N6-[(benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-L-lysyl]amino}ethyl)-N2-(tert-butoxycarbonyl)-L-tryptophanamide
• 英文别名: tert-butyl N-[(2S)-3-(1H-indol-3-yl)-1-[2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-(phenylmethoxycarbonylamino)hexanoyl]amino]ethylamino]-1-oxopropan-2-yl]carbamate
• CAS: 1186090-20-9
• 化学式: C₃₇H₅₂N₆O₈
• 分子量: 708.855
• InChiKey: MLBWEKGWZVBFRO-KYJUHHDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  51
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  189
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(2-{[N6-[(benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-L-lysyl]amino}ethyl)-N2-(tert-butoxycarbonyl)-L-tryptophanamide 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以70%的产率得到N2-(tert-butoxycarbonyl)-N-(2-{[N2-(tert-butoxycarbonyl)-L-lysyl]amino}ethyl)-L-(tryptophanamide)
  参考文献：
  名称：

  Fluorescence and mass spectrometry studies of the interaction between naproxen and synthetic pseudopeptidic models in organic media

  摘要：

  Time-resolved/steady-state fluorescence and mass spectrometry measurements have shown the preferential binding of a non-steroidal anti-inflammatory drug (NSAID) like naproxen 4 to a synthetic pseudopeptidic receptor built using Phe (9), i.e., bearing an aromatic ring, compared to another model synthesized using Lys (8), i.e., lacking such aromatic ring but with a basic binding site. The quenching of the emission of naproxen by models 8 and 9 has been measured in solvents of different nature and analyzed by means of the Stern-Volmer methodology. In non-polar solvent (dichloromethane) the fluorescence of 4 is quenched to a higher extent by 8 than by 9 but in polar medium (methanol) the opposite occurs. The result in methanol is compatible with the existence of pi-pi stacking interactions between the aromatic rings of naproxen and the aromatic ring of 9. In order to proof this model, mass spectrometry measurements have confirmed the higher stability of the complex formed by 4 and 9 over the related one formed with 8. The observed phenomenon could help to understand the importance of aromaticity in the interactions between NSAIDs and more complex biological macromolecules like misfolded proteins, involved in the development of Alzheimer's disease and other neuropathologies. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.031
• 作为产物：
  描述：

  N-Boc-N'-Cbz-L-赖氨酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N-(2-{[N6-[(benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-L-lysyl]amino}ethyl)-N2-(tert-butoxycarbonyl)-L-tryptophanamide
  参考文献：
  名称：

  对称仲烷二胺的有效单酰化和不对称二酰化烷二胺的合成。一种新的基于 L-脯氨酸的有机催化剂

  摘要：

  通过使用 PyBOP-HOBt 作为偶联剂，在室温下，在 DIEA 的存在下，开发了一种简单的程序，用于将几种未保护的链烷二胺与羧酸进行单酰化。伯链烷二胺的产率适中，直链或环状仲胺的产率从好到极好。为了说明这些单酰化产物的效用，合成了六种不对称的二酰化链烷二胺。此外，这些化合物之一被评估为不对称羟醛反应中的有机催化剂。

  DOI：

  10.24820/ark.5550190.p011.054

文献信息

• Fluorescence and mass spectrometry studies of the interaction between naproxen and synthetic pseudopeptidic models in organic media
  作者：M. Isabel Burguete、Ghinwa Fawaz、Francisco Galindo、M. Ángeles Izquierdo、Santiago V. Luis、Jean Martínez、Xavier J. Salom-Roig

  DOI：10.1016/j.tet.2009.07.031

  日期：2009.9

  Time-resolved/steady-state fluorescence and mass spectrometry measurements have shown the preferential binding of a non-steroidal anti-inflammatory drug (NSAID) like naproxen 4 to a synthetic pseudopeptidic receptor built using Phe (9), i.e., bearing an aromatic ring, compared to another model synthesized using Lys (8), i.e., lacking such aromatic ring but with a basic binding site. The quenching of the emission of naproxen by models 8 and 9 has been measured in solvents of different nature and analyzed by means of the Stern-Volmer methodology. In non-polar solvent (dichloromethane) the fluorescence of 4 is quenched to a higher extent by 8 than by 9 but in polar medium (methanol) the opposite occurs. The result in methanol is compatible with the existence of pi-pi stacking interactions between the aromatic rings of naproxen and the aromatic ring of 9. In order to proof this model, mass spectrometry measurements have confirmed the higher stability of the complex formed by 4 and 9 over the related one formed with 8. The observed phenomenon could help to understand the importance of aromaticity in the interactions between NSAIDs and more complex biological macromolecules like misfolded proteins, involved in the development of Alzheimer's disease and other neuropathologies. (C) 2009 Elsevier Ltd. All rights reserved.
• Efficient monoacylation of symmetrical secondary alkanediamines and synthesis of unsymmetrical diacylated alkanediamines. A new L-proline-based organocatalyst
  作者：Laure Moulat、Jean Martinez、Xavier J. Salom-Roig

  DOI：10.24820/ark.5550190.p011.054

  日期：——

  developed for the monoacylation of several unprotected alkanediamines with carboxylic acids by using PyBOP-HOBt as coupling agent in the presence of DIEA at room temperature. Yields were moderate with primary alkanediamines and good to excellent with linear or cyclic secondary ones. To illustrate the utility of these monoacylated products, six unsymmetrical diacylated alkanediamines were synthesized

  通过使用 PyBOP-HOBt 作为偶联剂，在室温下，在 DIEA 的存在下，开发了一种简单的程序，用于将几种未保护的链烷二胺与羧酸进行单酰化。伯链烷二胺的产率适中，直链或环状仲胺的产率从好到极好。为了说明这些单酰化产物的效用，合成了六种不对称的二酰化链烷二胺。此外，这些化合物之一被评估为不对称羟醛反应中的有机催化剂。