6-diethoxyphosphorylmethyl-3,9-ditosyl-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene | 308089-00-1

• 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: 6-diethoxyphosphorylmethyl-3,9-ditosyl-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene
• 英文别名: 6-(Diethoxyphosphorylmethyl)-3,9-bis-(4-methylphenyl)sulfonyl-3,6,9,15-tetrazabicyclo[9.3.1]pentadeca-1(15),11,13-triene
• CAS: 308089-00-1
• 化学式: C₃₀H₄₁N₄O₇PS₂
• 分子量: 664.784
• InChiKey: LMABBPDUXBIPLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  143
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  氯乙酸 、 6-diethoxyphosphorylmethyl-3,9-ditosyl-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene 在 硫酸 、 sodium hydroxide 作用下， 反应 24.17h， 以60%的产率得到3,9-bis(carboxymethyl)-6-dihydroxyphosphorylmethyl-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene
  参考文献：
  名称：

  [GdPCP2A(H₂O)₂]^-: A Paramagnetic Contrast Agent Designed for Improved Applications in Magnetic Resonance Imaging

  摘要：

  A novel ligand based on a pyridine-containing macrocycle bearing two acetic and one methylenephosphonic arms (PCP2A) has been synthesized. An efficient synthesis of PCP2A is based on the macrocyclization reaction between 2,6-bis(chloromethyl)pyridine and a 1,4,7-triazaheptane derivative bearing a methylenephosphonate group on N-4. The Gd(III) complex of PCP2A displays characteristic properties which make it a very promising contrast agent for improved applications in magnetic resonance imaging. In fact it shows (i) a very high stability constant (log K-GdPCP2A = 23.4) which should guarantee against the in vivo release of toxic free Gd(III) ions and free ligand molecules and (ii) a relaxivity that is about 2 times higher than the values reported for contrast agents currently used in the clinical practice. Its high relaxivity is the result of the presence of two water molecules in the inner coordination sphere and a significant contribution from water molecule(s) hydrogen bonded to the phosphonate group. Moreover, the inner sphere water molecules are involved in an exchange with the bulk water which is relatively fast. This property is important for the attainment of an even higher relaxivity once the molecular reorientation rate of the [GdPCP2A(H2O)(2)](-) moiety is lengthened by means of conjugation to a macromolecular substrate.

  DOI：

  10.1021/jm000983a
• 作为产物：
  描述：

  二乙基氨基甲烷膦酸酯 在 potassium carbonate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 22.0h， 生成 6-diethoxyphosphorylmethyl-3,9-ditosyl-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene
  参考文献：
  名称：

  [GdPCP2A(H₂O)₂]^-: A Paramagnetic Contrast Agent Designed for Improved Applications in Magnetic Resonance Imaging

  摘要：

  A novel ligand based on a pyridine-containing macrocycle bearing two acetic and one methylenephosphonic arms (PCP2A) has been synthesized. An efficient synthesis of PCP2A is based on the macrocyclization reaction between 2,6-bis(chloromethyl)pyridine and a 1,4,7-triazaheptane derivative bearing a methylenephosphonate group on N-4. The Gd(III) complex of PCP2A displays characteristic properties which make it a very promising contrast agent for improved applications in magnetic resonance imaging. In fact it shows (i) a very high stability constant (log K-GdPCP2A = 23.4) which should guarantee against the in vivo release of toxic free Gd(III) ions and free ligand molecules and (ii) a relaxivity that is about 2 times higher than the values reported for contrast agents currently used in the clinical practice. Its high relaxivity is the result of the presence of two water molecules in the inner coordination sphere and a significant contribution from water molecule(s) hydrogen bonded to the phosphonate group. Moreover, the inner sphere water molecules are involved in an exchange with the bulk water which is relatively fast. This property is important for the attainment of an even higher relaxivity once the molecular reorientation rate of the [GdPCP2A(H2O)(2)](-) moiety is lengthened by means of conjugation to a macromolecular substrate.

  DOI：

  10.1021/jm000983a

文献信息

• [GdPCP2A(H₂O)₂]^-: A Paramagnetic Contrast Agent Designed for Improved Applications in Magnetic Resonance Imaging
  作者：Silvio Aime、Mauro Botta、Luca Frullano、Simonetta Geninatti Crich、Giovanni Giovenzana、Roberto Pagliarin、Giovanni Palmisano、Federico Riccardi Sirtori、Massimo Sisti

  DOI：10.1021/jm000983a

  日期：2000.10.1

  A novel ligand based on a pyridine-containing macrocycle bearing two acetic and one methylenephosphonic arms (PCP2A) has been synthesized. An efficient synthesis of PCP2A is based on the macrocyclization reaction between 2,6-bis(chloromethyl)pyridine and a 1,4,7-triazaheptane derivative bearing a methylenephosphonate group on N-4. The Gd(III) complex of PCP2A displays characteristic properties which make it a very promising contrast agent for improved applications in magnetic resonance imaging. In fact it shows (i) a very high stability constant (log K-GdPCP2A = 23.4) which should guarantee against the in vivo release of toxic free Gd(III) ions and free ligand molecules and (ii) a relaxivity that is about 2 times higher than the values reported for contrast agents currently used in the clinical practice. Its high relaxivity is the result of the presence of two water molecules in the inner coordination sphere and a significant contribution from water molecule(s) hydrogen bonded to the phosphonate group. Moreover, the inner sphere water molecules are involved in an exchange with the bulk water which is relatively fast. This property is important for the attainment of an even higher relaxivity once the molecular reorientation rate of the [GdPCP2A(H2O)(2)](-) moiety is lengthened by means of conjugation to a macromolecular substrate.