tetraethyl 3-chloroaminopropyl 1,1-bis(phosphonate) | 1006102-76-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: tetraethyl 3-chloroaminopropyl 1,1-bis(phosphonate)
• 英文别名: N-[3,3-bis(diethoxyphosphoryl)propyl]-2-chloroacetamide
• CAS: 1006102-76-6
• 化学式: C₁₃H₂₈ClNO₇P₂
• 分子量: 407.768
• InChiKey: LDEGYTBEOUPIRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tetraethyl 3-chloroaminopropyl 1,1-bis(phosphonate) 、 三-叔-丁基1,4,7,10-四氮杂环十二烷-1,4,7-三乙酸酯氢溴酸盐 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 96.0h， 生成 Tert-butyl 2-[4-[2-[3,3-bis(diethoxyphosphoryl)propylamino]-2-oxoethyl]-7,10-bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-1,4,7,10-tetrazacyclododec-1-yl]acetate
  参考文献：
  名称：

  Lanthanide(III) Complexes of Bis(phosphonate) Monoamide Analogues of DOTA: Bone-Seeking Agents for Imaging and Therapy

  摘要：

  Lanthanide complexes of DOTA derivatives 2a (BPAMD) and 2b (BPAPD), having a monoamide pendant arm with a bis(phosphonate) moiety, were comparatively tested for application in MRI, radiotherapy, and bone pain palliation. H-1, P-31, and O-17 NMR spectroscopy show that they are nine-coordinated, with one water molecule in the first coordination sphere of the Ln(III) ion. The bis(phosphonate) moieties are not coordinated to the lanthanide and predominantly mono- and diprotonated at physiological pH. The parameters governing the longitudinal relaxivities of the Gd complexes are similar to those of other monoamides of DOTA reported in the literature. Upon adsorption on hydroxyapatite, the relaxivities at 20 MHz and 25 degrees C of Gd-2a and Gd-2b were 22.1 and 11 s(-1) mM(-1), respectively. An in vivo gamma-ray imaging study showed that the Lu-177 complexes of 2a and 2b have a high affinity for bones, particularly for growth plates and teeth with a prolonged retention.

  DOI：

  10.1021/jm7012776
• 作为产物：
  描述：

  氯乙酰氯 、 tetraethyl 3-amino-propane-1,1-bisphosphonate 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以89%的产率得到tetraethyl 3-chloroaminopropyl 1,1-bis(phosphonate)
  参考文献：
  名称：

  Lanthanide(III) Complexes of Bis(phosphonate) Monoamide Analogues of DOTA: Bone-Seeking Agents for Imaging and Therapy

  摘要：

  Lanthanide complexes of DOTA derivatives 2a (BPAMD) and 2b (BPAPD), having a monoamide pendant arm with a bis(phosphonate) moiety, were comparatively tested for application in MRI, radiotherapy, and bone pain palliation. H-1, P-31, and O-17 NMR spectroscopy show that they are nine-coordinated, with one water molecule in the first coordination sphere of the Ln(III) ion. The bis(phosphonate) moieties are not coordinated to the lanthanide and predominantly mono- and diprotonated at physiological pH. The parameters governing the longitudinal relaxivities of the Gd complexes are similar to those of other monoamides of DOTA reported in the literature. Upon adsorption on hydroxyapatite, the relaxivities at 20 MHz and 25 degrees C of Gd-2a and Gd-2b were 22.1 and 11 s(-1) mM(-1), respectively. An in vivo gamma-ray imaging study showed that the Lu-177 complexes of 2a and 2b have a high affinity for bones, particularly for growth plates and teeth with a prolonged retention.

  DOI：

  10.1021/jm7012776

文献信息

• Lanthanide(III) Complexes of Bis(phosphonate) Monoamide Analogues of DOTA: Bone-Seeking Agents for Imaging and Therapy
  作者：Tomáš Vitha、Vojtěch Kubíček、Petr Hermann、Luce Vander Elst、Robert N. Muller、Zvonimir I. Kolar、Hubert T. Wolterbeek、Wouter A.P. Breeman、Ivan Lukeš、Joop A. Peters

  DOI：10.1021/jm7012776

  日期：2008.2.1

  Lanthanide complexes of DOTA derivatives 2a (BPAMD) and 2b (BPAPD), having a monoamide pendant arm with a bis(phosphonate) moiety, were comparatively tested for application in MRI, radiotherapy, and bone pain palliation. H-1, P-31, and O-17 NMR spectroscopy show that they are nine-coordinated, with one water molecule in the first coordination sphere of the Ln(III) ion. The bis(phosphonate) moieties are not coordinated to the lanthanide and predominantly mono- and diprotonated at physiological pH. The parameters governing the longitudinal relaxivities of the Gd complexes are similar to those of other monoamides of DOTA reported in the literature. Upon adsorption on hydroxyapatite, the relaxivities at 20 MHz and 25 degrees C of Gd-2a and Gd-2b were 22.1 and 11 s(-1) mM(-1), respectively. An in vivo gamma-ray imaging study showed that the Lu-177 complexes of 2a and 2b have a high affinity for bones, particularly for growth plates and teeth with a prolonged retention.