(S)-4-benzyl-3,6,9-tirs(carboxymethyl)-1,11-bis(methylamino)-3,6,9-triazaundeca-1,11-dione | 748781-94-4

• 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: (S)-4-benzyl-3,6,9-tirs(carboxymethyl)-1,11-bis(methylamino)-3,6,9-triazaundeca-1,11-dione
• 英文别名: 4-benzyl-3,6,9-tris(carboxymethyl)-1,11-bis(methylamino)-3,6,9-triazaundeca-1,11-dione
• CAS: 748781-94-4
• 化学式: C₂₃H₃₅N₅O₈
• 分子量: 509.56
• InChiKey: GYAWVQYSBRRKJS-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.75
• 重原子数：
  36.0
• 可旋转键数：
  18.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  179.82
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  gadolinium(III) chloride 、 (S)-4-benzyl-3,6,9-tirs(carboxymethyl)-1,11-bis(methylamino)-3,6,9-triazaundeca-1,11-dione 以 水 为溶剂， 生成 Gd-(S)-C₄Bz-DTPA-BMA
  参考文献：
  名称：

  New Bifunctional Contrast Agents: Bis‐Amide Derivatives of C ‐Substituted Gd‐DTPA

  摘要：

  AbstractIn order to expand upon and confirm previous observations on the positive and adverse roles played by the functionalization and substitution of the parent MRI contrast agent Gd‐DTPA, two new bi‐functionalized contrast agents namely Gd‐(S)‐EOB‐DTPA‐BMA and Gd‐(S)‐C4Bz‐DTPA‐BMA have been synthesized, purified, and characterized by multinuclear NMR studies. Water 1H nuclear magnetic relaxation dispersion profiles were recorded at several temperatures. τR was determined by 2H NMR on the diamagnetic lanthanum complex. τM, the water residence time, was obtained by 17O NMR measurements and the stability versus transmetallation by zinc was evaluated by proton relaxometry. The residence time of water molecules in the first coordination sphere of the Gd complexes has confirmed the antagonistic effects of amide functions and C‐4 substitution on the reduction of the water residence time, a critical parameter of relaxivity. This C‐4 position is thus particularly appropriate for the substitution required by the design of new contrast agents covalently bound to macromolecules or carrying specific vectors. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejic.200300457
• 作为产物：
  描述：

  (S)-4-benzyl-3,6,9-tris(carboxymethyl)-3,6,9-triazaundecanedioic acid 在 吡啶 、 乙酸酐 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 (S)-4-benzyl-3,6,9-tirs(carboxymethyl)-1,11-bis(methylamino)-3,6,9-triazaundeca-1,11-dione
  参考文献：
  名称：

  New Bifunctional Contrast Agents: Bis‐Amide Derivatives of C ‐Substituted Gd‐DTPA

  摘要：

  AbstractIn order to expand upon and confirm previous observations on the positive and adverse roles played by the functionalization and substitution of the parent MRI contrast agent Gd‐DTPA, two new bi‐functionalized contrast agents namely Gd‐(S)‐EOB‐DTPA‐BMA and Gd‐(S)‐C4Bz‐DTPA‐BMA have been synthesized, purified, and characterized by multinuclear NMR studies. Water 1H nuclear magnetic relaxation dispersion profiles were recorded at several temperatures. τR was determined by 2H NMR on the diamagnetic lanthanum complex. τM, the water residence time, was obtained by 17O NMR measurements and the stability versus transmetallation by zinc was evaluated by proton relaxometry. The residence time of water molecules in the first coordination sphere of the Gd complexes has confirmed the antagonistic effects of amide functions and C‐4 substitution on the reduction of the water residence time, a critical parameter of relaxivity. This C‐4 position is thus particularly appropriate for the substitution required by the design of new contrast agents covalently bound to macromolecules or carrying specific vectors. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejic.200300457