TREN-Gly-1-Me-3,2-HOPO | 518046-68-9

• 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: TREN-Gly-1-Me-3,2-HOPO
• 英文别名: N-[2-[2-[bis[2-[[2-[(3-hydroxy-1-methyl-2-oxopyridine-4-carbonyl)amino]acetyl]amino]ethyl]amino]ethylamino]-2-oxoethyl]-3-hydroxy-1-methyl-2-oxopyridine-4-carboxamide
• CAS: 518046-68-9
• 化学式: C₃₃H₄₂N₁₀O₁₂
• 分子量: 770.756
• InChiKey: ZQJOYFNTDUGCER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  55
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  300
• 氢给体数：
  9
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  gadolinium(III) chloride 、 TREN-Gly-1-Me-3,2-HOPO 在 氨 作用下， 以 水 为溶剂， 反应 2.0h， 以71%的产率得到
  参考文献：
  名称：

  WO2007/121453

  摘要：

  公开号：
• 作为产物：
  描述：

  TREN-Gly-1-Me-3,2-HOPO, benzyl protected 在 5%-palladium/activated carbon 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 6.0h， 以62%的产率得到TREN-Gly-1-Me-3,2-HOPO
  参考文献：
  名称：

  Hydroxypyridonate and hydroxypyrimidinone chelating agents

  摘要：

  本发明提供了羟基吡啶酮和羟基嘧啶酮螯合剂。还提供了这些剂的Gd(III)配合物，这些配合物可用作磁共振成像的造影增强剂。该发明还提供了制备本发明化合物的方法，以及在磁共振成像应用中使用这些化合物的方法。

  公开号：

  US20050008570A1

文献信息

• The Effect of Ligand Scaffold Size on the Stability of Tripodal Hydroxypyridonate Gadolinium Complexes
  作者：Brendon O'Sullivan、Dan M. J. Doble、Marlon K. Thompson、Carsten Siering、Jide Xu、Mauro Botta、Silvio Aime、Kenneth N. Raymond

  DOI：10.1021/ic0261575

  日期：2003.4.1

  The variation of the size of the capping scaffold which connects the hydroxylpyridonate (HOPO) binding units in a series of tripodal chelators for gadolinium (Gd) complexes has been investigated. A new analogue of TREN-1-Me-3,2-HOPO (1) (TREN = tri(ethylamine)amine) was synthesized: TREN-Gly-1-Me-3,2-HOPO (2) features a glycine spacer between the TREN cap and HOPO binding unit. TRPN-1-Me-3,2-HOPO (3) has a propylene-bridged cap, as compared to the ethylene bridges within the TREN cap of the parent complex, Thermodynamic equilibrium constants for the acid-base properties of 2 and the Gd3+, complexation strength of 2 and 3 were measured and are compared with that of the parent ligand. The most basic ligand is 2 while 3 is the most acidic, Both 2 and 3 form Gd3+ complexes of similar stability (pGd = 16.7 and 15.6, respectively) and are less stable than the parent complex Gd-1 (pGd = 19.2). Two of the three complexes are more stable than the bis(methylamide)diethylenetriamine pentaacetate complex Gd(DTPA-BMA) (pGd = 157) while the other is of comparable stability. Enlargement of the ligand scaffold decreases the stability of the Gd3+ complexes and indicates that the TREN scaffold is superior to the TRPN and TREN-Gly scaffolds. The proton relaxivity of Gd-2 is 6.6 mM(-1) s(-1) (20 MHz, 25 degreesC, pH 7.3), somewhat lower than the parent Gd-1 but higher than that of the MRI contrast agents in clinical practice, The pH-independent relaxivity of Gd-2 is uncharacteristic of this family of complexes and is discussed.