N-δ-bromopentanoyl amantadine | 54059-82-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-δ-bromopentanoyl amantadine
• 英文别名: N-(1-adamantyl)-5-bromopentanamide
• CAS: 54059-82-4
• 化学式: C₁₅H₂₄BrNO
• 分子量: 314.266
• InChiKey: WTSBTVXPWNRBNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.933
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-δ-bromopentanoyl amantadine 在 溶剂黄146 、 硫脲 作用下， 以 乙醇 为溶剂， 反应 52.0h， 生成 N-adamantyl-3-(pyridin-2-yldisulfanyl)pentanamide
  参考文献：
  名称：

  介孔二氧化硅纳米粒子的药物封装和释放：表面官能团的影响

  摘要：

  介孔二氧化硅纳米颗粒（MSNP）已被广泛用作刺激药物传递的药物载体。本文中，采用了一种催化筛选技术来分析链长，末端基团和MSNP表面上二硫键连接的功能性配体的密度对载药量和谷胱甘肽触发的药物释放动力学的影响。具有中等长度（5个碳原子）和与β-环糊精环复合的庞大末端基团（环己基）的配体显示出最高的载药量和良好的释放动力学。另外，减少功能性配体的表面覆盖导致药物释放的增加。通过使用功能化MSNP在黑色素瘤细胞系（B16-F10）上进行的体外药物递送实验进一步支持了这一结论。

  DOI：

  10.1002/chem.201403551
• 作为产物：
  描述：

  5-溴戊酸 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 N-δ-bromopentanoyl amantadine
  参考文献：
  名称：

  β-Cyclodextrin Host−Guest Complexes Probed under Thermodynamic Equilibrium:  Thermodynamics and AFM Force Spectroscopy

  摘要：

  The rupture forces of individual host-guest complexes between beta-cycloclextrin (beta-CD) heptathioether monolayers on Au(111) and several surface-confined guests were measured in aqueous medium by single molecule force spectroscopy using an atomic force microscope. Anilyl, toluidyl, tert-butylphenyl, and adamantylthiols (0.2-1%) were immobilized in mixed monolayers with 2-mercaptoethanol on gold-coated AFM tips. For all guests and for all surface coverages, the force-displacement curves measured between the functionalized tips and monolayers of beta-CD exhibited single, as well as multiple, pull-off events. The histograms of the pull-off forces showed several maxima at equidistant forces, with force quanta characteristic for each guest of 39 +/- 15, 45 +/- 15, 89 +/- 15, and 102 +/- 15 pN, respectively. These force quanta were independent of the loading rate, indicating that, because of the fast complexation/ decomplexation kinetics, the rupture forces were probed under thermodynamic equilibrium. The force values followed the same trend as the free binding energy DeltaG(o) measured for model guest compounds in solution or on beta-CD monolayers, as determined by microcalorimetry and surface plasmon resonance measurements, respectively. A descriptive model was developed to correlate quantitatively the pull-off force values with the DeltaG(o) of the complexes, based on the evaluation of the energy potential landscape of tip-surface interaction.

  DOI：

  10.1021/ja0383569

文献信息

• Hybridization of amantadine with gardenamide A enhances NMDA antagonism and in vivo anti-PD effects
  作者：Wenda Zhu、Yiping Fan、Yanbing Li、Lizhi Peng、Yifang Li、Fengxia Yan、Jiaqiang Zhao、Lei Zhang、Hiroshi Kurihara、Rongrong He、Heru Chen

  DOI：10.1016/j.bioorg.2022.106223

  日期：2023.1
• Drug Encapsulation and Release by Mesoporous Silica Nanoparticles: The Effect of Surface Functional Groups
  作者：Si Yu Tan、Chung Yen Ang、Peizhou Li、Qi Ming Yap、Yanli Zhao

  DOI：10.1002/chem.201403551

  日期：2014.9.1

  Mesoporous silica nanoparticles (MSNPs) have been widely used as drug carriers for stimuli‐responsive drug delivery. Herein, a catalysis screening technique was adopted for analyzing the effects of chain length, terminal group, and density of disulfide‐appended functional ligands on the surface of MSNPs on drug‐loading capacity and glutathione‐triggered drug‐release kinetics. The ligand with an intermediate

  介孔二氧化硅纳米颗粒（MSNP）已被广泛用作刺激药物传递的药物载体。本文中，采用了一种催化筛选技术来分析链长，末端基团和MSNP表面上二硫键连接的功能性配体的密度对载药量和谷胱甘肽触发的药物释放动力学的影响。具有中等长度（5个碳原子）和与β-环糊精环复合的庞大末端基团（环己基）的配体显示出最高的载药量和良好的释放动力学。另外，减少功能性配体的表面覆盖导致药物释放的增加。通过使用功能化MSNP在黑色素瘤细胞系（B16-F10）上进行的体外药物递送实验进一步支持了这一结论。
• β-Cyclodextrin Host−Guest Complexes Probed under Thermodynamic Equilibrium:  Thermodynamics and AFM Force Spectroscopy
  作者：Tommaso Auletta、Menno R. de Jong、Alart Mulder、Frank C. J. M. van Veggel、Jurriaan Huskens、David N. Reinhoudt、Shan Zou、Szczepan Zapotoczny、Holger Schönherr、G. Julius Vancso、Laurens Kuipers

  DOI：10.1021/ja0383569

  日期：2004.2.1

  The rupture forces of individual host-guest complexes between beta-cycloclextrin (beta-CD) heptathioether monolayers on Au(111) and several surface-confined guests were measured in aqueous medium by single molecule force spectroscopy using an atomic force microscope. Anilyl, toluidyl, tert-butylphenyl, and adamantylthiols (0.2-1%) were immobilized in mixed monolayers with 2-mercaptoethanol on gold-coated AFM tips. For all guests and for all surface coverages, the force-displacement curves measured between the functionalized tips and monolayers of beta-CD exhibited single, as well as multiple, pull-off events. The histograms of the pull-off forces showed several maxima at equidistant forces, with force quanta characteristic for each guest of 39 +/- 15, 45 +/- 15, 89 +/- 15, and 102 +/- 15 pN, respectively. These force quanta were independent of the loading rate, indicating that, because of the fast complexation/ decomplexation kinetics, the rupture forces were probed under thermodynamic equilibrium. The force values followed the same trend as the free binding energy DeltaG(o) measured for model guest compounds in solution or on beta-CD monolayers, as determined by microcalorimetry and surface plasmon resonance measurements, respectively. A descriptive model was developed to correlate quantitatively the pull-off force values with the DeltaG(o) of the complexes, based on the evaluation of the energy potential landscape of tip-surface interaction.