[4-({[Bis-(diethoxy-phosphoryl)-methyl]-carbamoyl}-methyl)-7,10-bis-tert-butoxycarbonylmethyl-1,4,7,10-tetraaza-cyclododec-1-yl]-acetic acid tert-butyl ester | 872469-61-9

• 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: [4-({[Bis-(diethoxy-phosphoryl)-methyl]-carbamoyl}-methyl)-7,10-bis-tert-butoxycarbonylmethyl-1,4,7,10-tetraaza-cyclododec-1-yl]-acetic acid tert-butyl ester
• CAS: 872469-61-9
• 化学式: C₃₇H₇₃N₅O₁₃P₂
• 分子量: 857.96
• InChiKey: IIUOFUZLBGSARW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  57.0
• 可旋转键数：
  19.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  192.02
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  [4-({[Bis-(diethoxy-phosphoryl)-methyl]-carbamoyl}-methyl)-7,10-bis-tert-butoxycarbonylmethyl-1,4,7,10-tetraaza-cyclododec-1-yl]-acetic acid tert-butyl ester 在 氢溴酸 、 溶剂黄146 作用下， 反应 24.0h， 以39%的产率得到(4-{[(Bis-phosphono-methyl)-carbamoyl]-methyl}-7,10-bis-carboxymethyl-1,4,7,10-tetraaza-cyclododec-1-yl)-acetic acid
  参考文献：
  名称：

  A Bisphosphonate Monoamide Analogue of DOTA:  A Potential Agent for Bone Targeting

  摘要：

  A new macrocyclic DOTA-like ligand (BPAMD) for bone imaging and therapy containing a monoamide bis(phosphonic acid) bone-seeking group was designed and synthesized. Its lanthanide(ill) complexes were prepared and characterized by H-1 and P-31 INIMR spectroscopy. The Gd(III)-BPAMD complex was investigated in detail by H-1 and O-17 relaxometric studies to inspect parameters relevant for its potential application as an MRI contrast agent. Sorption experiments were conducted with Gd(Ill) and Tb(III) complexes using hydroxyapatite (HA) as a model of bone surface. Very effective uptake of the Gd-BPAMD complex by the HA surface was observed in NMR experiments. Radiochemical studies with the (Tb-160-BPAMD)-HA system proved the sorption to be remarkably fast and strong on one hand and fully reversible on the other hand. The strong (Gd-BPAMD)-HA interaction was also supported by H-1 NMRD measurements in the presence of a hydroxyapatite slurry, which showed an increase of the rotational correlation time upon adsorption of the complex on the HA surface, resulting in a significant relaxivity enhancement. The amide-bis(phosphonate) moiety is the only factor responsible for the binding of the complex to HA.

  DOI：

  10.1021/ja054905u
• 作为产物：
  描述：

  tetraethyl (N,N-dibenzyl)aminomethyl-bis(phosphonate) 在 palladium on activated charcoal 氢气 、 sodium carbonate 、 potassium carbonate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 48.0h， 生成 [4-({[Bis-(diethoxy-phosphoryl)-methyl]-carbamoyl}-methyl)-7,10-bis-tert-butoxycarbonylmethyl-1,4,7,10-tetraaza-cyclododec-1-yl]-acetic acid tert-butyl ester
  参考文献：
  名称：

  A Bisphosphonate Monoamide Analogue of DOTA:  A Potential Agent for Bone Targeting

  摘要：

  A new macrocyclic DOTA-like ligand (BPAMD) for bone imaging and therapy containing a monoamide bis(phosphonic acid) bone-seeking group was designed and synthesized. Its lanthanide(ill) complexes were prepared and characterized by H-1 and P-31 INIMR spectroscopy. The Gd(III)-BPAMD complex was investigated in detail by H-1 and O-17 relaxometric studies to inspect parameters relevant for its potential application as an MRI contrast agent. Sorption experiments were conducted with Gd(Ill) and Tb(III) complexes using hydroxyapatite (HA) as a model of bone surface. Very effective uptake of the Gd-BPAMD complex by the HA surface was observed in NMR experiments. Radiochemical studies with the (Tb-160-BPAMD)-HA system proved the sorption to be remarkably fast and strong on one hand and fully reversible on the other hand. The strong (Gd-BPAMD)-HA interaction was also supported by H-1 NMRD measurements in the presence of a hydroxyapatite slurry, which showed an increase of the rotational correlation time upon adsorption of the complex on the HA surface, resulting in a significant relaxivity enhancement. The amide-bis(phosphonate) moiety is the only factor responsible for the binding of the complex to HA.

  DOI：

  10.1021/ja054905u