diethylenetriamine-N-malonic acid | 1220057-33-9

• 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: diethylenetriamine-N-malonic acid
• 英文别名: 2-[2-(2-Aminoethylamino)ethylamino]propanedioic acid
• CAS: 1220057-33-9
• 化学式: C₇H₁₅N₃O₄
• 分子量: 205.214
• InChiKey: ZEVAIPGUTOEQGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.7
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  125
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  fac-[Re(CO)₃(H₂O)₃]OTf 、 diethylenetriamine-N-malonic acid 在 HCl 作用下， 以 水 为溶剂， 以42%的产率得到[fac-Re(CO)3(diethylenetriamine-N-malonate(1-)-NNO)]
  参考文献：
  名称：

  Coordination Modes of Multidentate Ligands infac-[Re(CO)₃(polyaminocarboxylate)] Analogues of^99mTc Radiopharmaceuticals. Dependence on Aqueous Solution Reaction Conditions

  摘要：

  We study Re analogues of Tc-99m renal agents to interpret previous results at the Tc-99m tracer level. The relative propensities of amine donors versus carboxylate oxygen donors of four L = polyaminocarboxylate ligands to coordinate in fac-[Re-1(CO)(3)L](n) complexes were assessed by examining the reaction of fac-[Re-1(CO)(3)(H2O)(3)](+) under conditions differing in acidity and temperature. All four L [N,N-bis-(2-aminoethyl)glycine (DTGH), N,N-ethylenediaminediacetic acid, diethylenetriamine-N-malonic acid, and diethylenetriamine-N-acetic acid] can coordinate as tridentate ligands while creating a dangling chain terminated in a carboxyl group. Dangling carboxyl groups facilitate renal clearance in fac-[(99)mTc(1)(CO)(3)L](n) agents. Under neutral conditions, the four ligands each gave two fac-[Re-1(CO)(3)L](n) products with HPLC traces correlating well with known traces of the fac-[Tc-99m(1)(CO)(3)L](n) mixtures. Such mixtures are common in renal agents because the needed dangling carboxyl group can compete for a coordination site. However, the HPLC separations needed to assess the biodistribution of a single tracer are impractical in a clinical setting. One goal in investigating this Re chemistry is to identify conditions for avoiding this problem of mixtures in preparations of fac-[Tc-99m(1)(CO)(3)L](n) renal tracers. After separation and isolation of the fac-[Re-1(CO)(3)L](n) products, NMR analysis of all products and single crystal X-ray crystallographic analysis of both DTGH products, as well as one product each from the other L, allowed us to establish coordination mode unambiguously. The product favored in acidic conditions has a dangling amine chain and more bound oxygen. The product favored in basic conditions has a dangling carboxyl chain and more bound nitrogen. At the elevated temperatures used for simulating tracer preparation, equilibration was facile (ca. 1 h or less), allowing selective formation of one product by utilizing acidic or basic conditions. The results of this fundamental study offer protocols and guidance useful for the design and preparation of fac-[Tc-99m(1)(CO)(3)L](n) agents consisting of a single tracer.

  DOI：

  10.1021/ic9017568

文献信息

• Coordination Modes of Multidentate Ligands in<i>fac</i>-[Re(CO)₃(polyaminocarboxylate)] Analogues of^99mTc Radiopharmaceuticals. Dependence on Aqueous Solution Reaction Conditions
  作者：Malgorzata Lipowska、Haiyang He、Xiaolong Xu、Andrew T. Taylor、Patricia A. Marzilli、Luigi G. Marzilli

  DOI：10.1021/ic9017568

  日期：2010.4.5

  We study Re analogues of Tc-99m renal agents to interpret previous results at the Tc-99m tracer level. The relative propensities of amine donors versus carboxylate oxygen donors of four L = polyaminocarboxylate ligands to coordinate in fac-[Re-1(CO)(3)L](n) complexes were assessed by examining the reaction of fac-[Re-1(CO)(3)(H2O)(3)](+) under conditions differing in acidity and temperature. All four L [N,N-bis-(2-aminoethyl)glycine (DTGH), N,N-ethylenediaminediacetic acid, diethylenetriamine-N-malonic acid, and diethylenetriamine-N-acetic acid] can coordinate as tridentate ligands while creating a dangling chain terminated in a carboxyl group. Dangling carboxyl groups facilitate renal clearance in fac-[(99)mTc(1)(CO)(3)L](n) agents. Under neutral conditions, the four ligands each gave two fac-[Re-1(CO)(3)L](n) products with HPLC traces correlating well with known traces of the fac-[Tc-99m(1)(CO)(3)L](n) mixtures. Such mixtures are common in renal agents because the needed dangling carboxyl group can compete for a coordination site. However, the HPLC separations needed to assess the biodistribution of a single tracer are impractical in a clinical setting. One goal in investigating this Re chemistry is to identify conditions for avoiding this problem of mixtures in preparations of fac-[Tc-99m(1)(CO)(3)L](n) renal tracers. After separation and isolation of the fac-[Re-1(CO)(3)L](n) products, NMR analysis of all products and single crystal X-ray crystallographic analysis of both DTGH products, as well as one product each from the other L, allowed us to establish coordination mode unambiguously. The product favored in acidic conditions has a dangling amine chain and more bound oxygen. The product favored in basic conditions has a dangling carboxyl chain and more bound nitrogen. At the elevated temperatures used for simulating tracer preparation, equilibration was facile (ca. 1 h or less), allowing selective formation of one product by utilizing acidic or basic conditions. The results of this fundamental study offer protocols and guidance useful for the design and preparation of fac-[Tc-99m(1)(CO)(3)L](n) agents consisting of a single tracer.