N2-(tert-butoxycarbonyl)-N-(2-{[N2-(tert-butoxycarbonyl)-L-lysyl]amino}ethyl)-L-(tryptophanamide) | 1186090-19-6

• 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: N2-(tert-butoxycarbonyl)-N-(2-{[N2-(tert-butoxycarbonyl)-L-lysyl]amino}ethyl)-L-(tryptophanamide)
• 英文别名: tert-butyl N-[(2S)-6-amino-1-[2-[[(2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]ethylamino]-1-oxohexan-2-yl]carbamate
• CAS: 1186090-19-6
• 化学式: C₂₉H₄₆N₆O₆
• 分子量: 574.721
• InChiKey: RMOLSROWIUXOSH-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  41
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  177
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N2-(tert-butoxycarbonyl)-N-(2-{[N2-(tert-butoxycarbonyl)-L-lysyl]amino}ethyl)-L-(tryptophanamide) 、 萘普生 以 甲醇 为溶剂， 生成
  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-(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

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.