3,5-bis-(dimethoxyphosphorylmethyl)benzoic acid diethoxyphosphorylmethylamide | 367927-29-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-bis-(dimethoxyphosphorylmethyl)benzoic acid diethoxyphosphorylmethylamide
• 英文别名: N-[[diethoxy(oxido)phosphaniumyl]methyl]-3,5-bis[[dimethoxy(oxido)phosphaniumyl]methyl]benzamide
• CAS: 367927-29-5
• 化学式: C₁₈H₃₂NO₁₀P₃
• 分子量: 515.374
• InChiKey: NJGWBKFMQURQOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  32
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  154
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,5-bis-(dimethoxyphosphorylmethyl)benzoic acid diethoxyphosphorylmethylamide 在 sodium hydride 、 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  RGD序列的第一个合成受体。

  摘要：

  [结构：见正文]优化的精氨酸受体单元与带有策略性放置的伯铵基团的半刚性接头的组合导致了第一个合成的RGD受体。它与游离RGD肽以及水中的cyclo（RGDfV）结合，缔合常数约为1000 M（-1）。RGD模拟物（例如苄am 6）未被识别，这使得新宿主成为对肽中的真实RGD序列具有选择性的新型受体的原型。

  DOI：

  10.1021/ol025976q
• 作为产物：
  描述：

  3,5-二甲基苯甲酸甲酯 在 偶氮二异丁腈 lithium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 四氯化碳 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 75.0h， 生成 3,5-bis-(dimethoxyphosphorylmethyl)benzoic acid diethoxyphosphorylmethylamide
  参考文献：
  名称：

  Optimization of a Synthetic Arginine Receptor. Systematic Tuning of Noncovalent Interactions

  摘要：

  The simple arginine binder I could be optimized by strengthening pi -cation as well as electrostatic interactions. Electron-donating or -withdrawing substituents in the 5-position provide experimental evidence for T-cation interactions, because binding energies increase by up to 0.6 kcal/mol due to a single benzene - guanidinium interaction. Even more effective is the introduction of a third phosphonate functionality at the correct distance, so that the guanidinium cation is recognized by optimal electrostatic and hydrogen bond interactions. Monte Carlo simulations and NOESY experiments confirm the expected complex geometries. The optimized host molecule 8 binds arginine half an order of magnitude more efficiently than the parent molecule.

  DOI：

  10.1021/jo0156161

文献信息

• Optimization of a Synthetic Arginine Receptor. Systematic Tuning of Noncovalent Interactions
  作者：Stephan Rensing、Markus Arendt、Andreas Springer、Thomas Grawe、Thomas Schrader

  DOI：10.1021/jo0156161

  日期：2001.8.1

  The simple arginine binder I could be optimized by strengthening pi -cation as well as electrostatic interactions. Electron-donating or -withdrawing substituents in the 5-position provide experimental evidence for T-cation interactions, because binding energies increase by up to 0.6 kcal/mol due to a single benzene - guanidinium interaction. Even more effective is the introduction of a third phosphonate functionality at the correct distance, so that the guanidinium cation is recognized by optimal electrostatic and hydrogen bond interactions. Monte Carlo simulations and NOESY experiments confirm the expected complex geometries. The optimized host molecule 8 binds arginine half an order of magnitude more efficiently than the parent molecule.
• The First Synthetic Receptor for the RGD Sequence
  作者：Stephan Rensing、Thomas Schrader

  DOI：10.1021/ol025976q

  日期：2002.6.1

  [structure: see text] The combination of an optimized arginine receptor unit with a semirigid linker carrying a strategically placed primary ammonium group leads to the first synthetic RGD receptor. It binds to the free RGD peptide as well as to cyclo(RGDfV) in water with association constants around 1000 M(-1). RGD mimetics such as benzamidine 6 are not recognized, rendering the new host a prototype

  [结构：见正文]优化的精氨酸受体单元与带有策略性放置的伯铵基团的半刚性接头的组合导致了第一个合成的RGD受体。它与游离RGD肽以及水中的cyclo（RGDfV）结合，缔合常数约为1000 M（-1）。RGD模拟物（例如苄am 6）未被识别，这使得新宿主成为对肽中的真实RGD序列具有选择性的新型受体的原型。