N-(4-nitrophenyl)propylenediamine-N',N'-diacetic acid | 775578-63-7

• 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: N-(4-nitrophenyl)propylenediamine-N',N'-diacetic acid
• 英文别名: p-N-(nitrophenyl)propylenediaminediacetic acid；2-[Carboxymethyl-[3-(4-nitroanilino)propyl]amino]acetic acid
• CAS: 775578-63-7
• 化学式: C₁₃H₁₇N₃O₆
• 分子量: 311.294
• InChiKey: LRJOORVMWBXFML-UHFFFAOYSA-N

物化性质

• 沸点：
  601.1±55.0 °C(Predicted)
• 密度：
  1.439±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  五羰基氯铼(I) 、 三乙胺 、 N-(4-nitrophenyl)propylenediamine-N',N'-diacetic acid 以 甲醇 为溶剂， 以93%的产率得到[Et3NH][Re(CO)3(p-N-(nitrophenyl)propylenediaminediaceticacid(-2H)]*H2O
  参考文献：
  名称：

  Ethylenediamine- and propylenediaminediacetic acid derivatives as ligands for the “fac-[M(CO)3]+” core (M=Re, 99mTc)

  摘要：

  The reaction of Re(CO)(5)Cl with o- or p-N-(nitrophenyl)ethylenediaminediacetic acid (H2L1, H2L2) and o- or p-N-(nitrophenyl)propylenediaminediacetic acid (H2L3, H2L4) in methanol leads to the formation of stable anionic [Et3NH][Re(CO)(3)(L)]-H2O complexes 1-4. These compounds have been characterized by means of IR, mass spectrometry, elemental analysis, NMR and conductimetry, as well as X-ray crystallography for 2 and 3. The [Re(CO)(3)](+) moiety is coordinated via the nitrogen of the iminodiacetic acid unit and two oxygens of monodentate carboxylate groups. In each case, the nitro group of the aromatic ring remains uncoordinated. The analogous technetium-99m complexes V and 3' were also prepared quantitatively by the reaction of H2L1 and H2L3, respectively, with the fac-[Tc-99m(CO)(3)(H2O)(3)](+) precursor in ethanol. The corresponding Re and Tc-99m compounds were shown to possess the same structure by means of HPLC studies. The high affinity of these ligands for the Tc(l) or Re(I) core, coupled with the easiness of their derivatization (by reduction of the nitro group in amino group), implies that the utilization of this ligand system to develop target-specific radiopharmaceuticals for diagnosis and therapy is promising. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2006.02.023
• 作为产物：
  描述：

  N-(p-nitrophenyl)-1,3-diaminopropane 在 sodium hydroxide 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 15.0h， 生成 N-(4-nitrophenyl)propylenediamine-N',N'-diacetic acid
  参考文献：
  名称：

  用于Re（I）有机金属化学的新型乙二胺或丙二胺二乙酸衍生物的设计与合成

  摘要：

  已经开发出一种新的合成新型方法，用于“ fac- [M（CO）3 ] + ”核心（M = 99m Tc，99 Tc或Re）的新型双功能螯合剂（BCA）。该策略包括方便地制备具有叔胺的这些三齿配体，所述叔胺带有两个羧酸官能团作为配位位点和一个芳香族氨基基团以偶联至生物载体。首次络合研究表明，这些化合物仅充当三齿配体（通过两种酸和叔胺官能团）。这些新配体的便捷合成及其对Re（I）的高亲和力使它们在生物医学应用中非常有前途。

  DOI：

  10.1016/j.tet.2003.11.058

文献信息

• Ethylenediamine- and propylenediaminediacetic acid derivatives as ligands for the “fac-[M(CO)3]+” core (M=Re, 99mTc)
  作者：Mustapha Allali、Sandra Cousinié、Marie Gressier、Christian Tessier、André L. Beauchamp、Yvon Coulais、Michèle Dartiguenave、Eric Benoist

  DOI：10.1016/j.ica.2006.02.023

  日期：2006.4

  The reaction of Re(CO)(5)Cl with o- or p-N-(nitrophenyl)ethylenediaminediacetic acid (H2L1, H2L2) and o- or p-N-(nitrophenyl)propylenediaminediacetic acid (H2L3, H2L4) in methanol leads to the formation of stable anionic [Et3NH][Re(CO)(3)(L)]-H2O complexes 1-4. These compounds have been characterized by means of IR, mass spectrometry, elemental analysis, NMR and conductimetry, as well as X-ray crystallography for 2 and 3. The [Re(CO)(3)](+) moiety is coordinated via the nitrogen of the iminodiacetic acid unit and two oxygens of monodentate carboxylate groups. In each case, the nitro group of the aromatic ring remains uncoordinated. The analogous technetium-99m complexes V and 3' were also prepared quantitatively by the reaction of H2L1 and H2L3, respectively, with the fac-[Tc-99m(CO)(3)(H2O)(3)](+) precursor in ethanol. The corresponding Re and Tc-99m compounds were shown to possess the same structure by means of HPLC studies. The high affinity of these ligands for the Tc(l) or Re(I) core, coupled with the easiness of their derivatization (by reduction of the nitro group in amino group), implies that the utilization of this ligand system to develop target-specific radiopharmaceuticals for diagnosis and therapy is promising. (c) 2006 Elsevier B.V. All rights reserved.
• Design and synthesis of new ethylenediamine or propylenediamine diacetic acid derivatives for Re(I) organometallic chemistry
  作者：Mustapha Allali、Eric Benoist、Nouzha Habbadi、Marie Gressier、Abdelaziz Souizi、Michèle Dartiguenave

  DOI：10.1016/j.tet.2003.11.058

  日期：2004.1

  First complexation study has shown that these compounds act exclusively as tridentate ligands (via the two acids and the tertiary amine functions). The convenient synthesis of these new ligands coupled with their high affinity for Re(I) make them quite promising for biomedical applications.

  已经开发出一种新的合成新型方法，用于“ fac- [M（CO）3 ] + ”核心（M = 99m Tc，99 Tc或Re）的新型双功能螯合剂（BCA）。该策略包括方便地制备具有叔胺的这些三齿配体，所述叔胺带有两个羧酸官能团作为配位位点和一个芳香族氨基基团以偶联至生物载体。首次络合研究表明，这些化合物仅充当三齿配体（通过两种酸和叔胺官能团）。这些新配体的便捷合成及其对Re（I）的高亲和力使它们在生物医学应用中非常有前途。