3-(4-aminophenyl)-2-(bis-tertbutoxycarbonylmethylamino)propionic acid | 1619224-41-7

• 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: 3-(4-aminophenyl)-2-(bis-tertbutoxycarbonylmethylamino)propionic acid
• CAS: 1619224-41-7
• 化学式: C₂₁H₃₂N₂O₆
• 分子量: 408.495
• InChiKey: PMXDKYNXEJGNGP-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  119.16
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-(4-aminophenyl)-2-(bis-tertbutoxycarbonylmethylamino)propionic acid 在 potassium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 32.75h， 生成 2,2',2''-(10-(2-(4-(2-(bis(carboxymethyl)amino)-2-carboxyethyl)phenylamino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetic acid
  参考文献：
  名称：

  Design and synthesis of calcium responsive magnetic resonance imaging agent: Its relaxation and luminescence studies

  摘要：

  Calcium concentration modulation both inside and outside cell is of considerable interest for nervous system function in normal and pathological conditions. MRI has potential for very high spatial resolution at molecular/cellular level. Design, synthesis and evaluation of Gd-DO3A-AME-NPHE, a calcium responsive MRI contrast agent is presented. The probe is comprised of a Gd3+-DO3A core coupled to iminoacetate coordinating groups for calcium induced relaxivity switching. In the absence of Ca2+ ions, inner sphere water binding to the Gd-DO3A-AME-NPHE is restricted with longitudinal relaxivity, r(1) =4.37 mM(-1) s(-1) at 4.7 T. However, addition of Ca2+ triggers a marked enhancement in r(1) = 6.99 mM(-1) s(-1) at 4.7 T (60% increase). The construct is highly selective for Ca2+ over competitive metal ions at extracellular concentration. The r(1) is modulated by changes in the hydration number (0.2 to 1.05), which was confirmed by luminescence emission lifetimes of the analogous Eu3+ complex. T-1 phantom images establish the capability of complex of visualizing changes in [Ca2+] by MRI. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.046
• 作为产物：
  描述：

  2-(bis-2-tert-butoxycarbonylmethylamino)-3-(4-nitrophenyl)propanoic acid 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 以90%的产率得到3-(4-aminophenyl)-2-(bis-tertbutoxycarbonylmethylamino)propionic acid
  参考文献：
  名称：

  Design and synthesis of calcium responsive magnetic resonance imaging agent: Its relaxation and luminescence studies

  摘要：

  Calcium concentration modulation both inside and outside cell is of considerable interest for nervous system function in normal and pathological conditions. MRI has potential for very high spatial resolution at molecular/cellular level. Design, synthesis and evaluation of Gd-DO3A-AME-NPHE, a calcium responsive MRI contrast agent is presented. The probe is comprised of a Gd3+-DO3A core coupled to iminoacetate coordinating groups for calcium induced relaxivity switching. In the absence of Ca2+ ions, inner sphere water binding to the Gd-DO3A-AME-NPHE is restricted with longitudinal relaxivity, r(1) =4.37 mM(-1) s(-1) at 4.7 T. However, addition of Ca2+ triggers a marked enhancement in r(1) = 6.99 mM(-1) s(-1) at 4.7 T (60% increase). The construct is highly selective for Ca2+ over competitive metal ions at extracellular concentration. The r(1) is modulated by changes in the hydration number (0.2 to 1.05), which was confirmed by luminescence emission lifetimes of the analogous Eu3+ complex. T-1 phantom images establish the capability of complex of visualizing changes in [Ca2+] by MRI. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.046