diethyl 3-amino-3,3-diphosphonopropyl(acetamido)malonate

• 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: diethyl 3-amino-3,3-diphosphonopropyl(acetamido)malonate
• 英文别名: ethyl N~2~-acetyl-2-(ethoxycarbonyl)-5,5-diphosphonoornithinate；(4-acetamido-1-amino-5-ethoxy-4-ethoxycarbonyl-5-oxo-1-phosphonopentyl)phosphonic acid
• 化学式: C₁₂H₂₄N₂O₁₁P₂
• 分子量: 434.277
• InChiKey: IBDYWGVABJKGSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.9
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  223
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  diethyl 3-amino-3,3-diphosphonopropyl(acetamido)malonate 在 盐酸 、 水 作用下， 反应 10.0h， 以75%的产率得到2,5-diamino-5,5-diphosphonovaleric acid hydrochloride
  参考文献：
  名称：

  2,5-Diamino-5,5-diphosphonovaleric Acid as a Ligand for an Osteotropic 188Re Radiopharmaceutical

  摘要：

  A modified method for the preparation of 2,5-diamino-5,5-diphosphonovaleric acid (DADP5) has been developed in the search for new synthetically available organic ligands to produce Re-188 radiopharmaceuticals with an increased accumulation in the bone tissue. Interaction of the obtained acid with Re-188 was studied by radio-TLC. An optimal system for separating unbound Re-188 and labeled complex in a yield of at least 95% was found. The biological distribution of Re-188-DADP5 was studied based on direct radiometric data. The osteotropicity of Re-188-DADP5 and its increased accumulation in bone fracture sites, which represent oncological pathology models, was detected at a level comparable to known radiopharmaceuticals.

  DOI：

  10.1134/s1070363218090037
• 作为产物：
  描述：

  ethyl-2-carbethoxy-2-acetylamino-2-cyanobutanoate 在 三溴化磷 、 亚磷酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以56%的产率得到diethyl 3-amino-3,3-diphosphonopropyl(acetamido)malonate
  参考文献：
  名称：

  Phosphorus-Containing Aminocarboxylic Acids: XV. α,ω-Diamino-ω,ω-diphosphonoalkylcarboxylic Acids

  摘要：

  A general method for the synthesis of phosphonic aminocarboxylic acids combining aminodiphosphonic and amino acid functions in one molecule was developed. Amino acids of a new type are AP-acids analogs, which are ligands of glutamate receptors that determine the processes of information transmission and processing in the central nervous system, and can also be promising compounds as new components of radiopharmaceuticals.

  DOI：

  10.1134/s1070363218050341

文献信息

• 2,5-Diamino-5,5-diphosphonovaleric Acid as a Ligand for an Osteotropic 188Re Radiopharmaceutical
  作者：G. S. Tsebrikova、V. V. Ragulin、V. E. Baulin、K. E. German、A. O. Malysheva、O. E. Klement’eva、G. E. Kodina、A. A. Larenkov、E. A. Lyamtseva、N. A. Taratonenkova、M. V. Zhukova、A. Yu. Tsivadze

  DOI：10.1134/s1070363218090037

  日期：2018.9

  A modified method for the preparation of 2,5-diamino-5,5-diphosphonovaleric acid (DADP5) has been developed in the search for new synthetically available organic ligands to produce Re-188 radiopharmaceuticals with an increased accumulation in the bone tissue. Interaction of the obtained acid with Re-188 was studied by radio-TLC. An optimal system for separating unbound Re-188 and labeled complex in a yield of at least 95% was found. The biological distribution of Re-188-DADP5 was studied based on direct radiometric data. The osteotropicity of Re-188-DADP5 and its increased accumulation in bone fracture sites, which represent oncological pathology models, was detected at a level comparable to known radiopharmaceuticals.
• Phosphorus-Containing Aminocarboxylic Acids: XV. α,ω-Diamino-ω,ω-diphosphonoalkylcarboxylic Acids
  作者：V. V. Ragulin

  DOI：10.1134/s1070363218050341

  日期：2018.5

  A general method for the synthesis of phosphonic aminocarboxylic acids combining aminodiphosphonic and amino acid functions in one molecule was developed. Amino acids of a new type are AP-acids analogs, which are ligands of glutamate receptors that determine the processes of information transmission and processing in the central nervous system, and can also be promising compounds as new components of radiopharmaceuticals.