10-(2-Ethoxy-3,4-dioxo-1-cyclobutenyl)-1,4,7,10-tetraazacyclododecan-2,4,7-triacetic acid tris(tert-butyl ester) | 221289-33-4

• 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: 10-(2-Ethoxy-3,4-dioxo-1-cyclobutenyl)-1,4,7,10-tetraazacyclododecan-2,4,7-triacetic acid tris(tert-butyl ester)
• CAS: 221289-33-4
• 化学式: C₃₂H₅₄N₄O₉
• 分子量: 638.802
• InChiKey: FCDHGUVOAPQDOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  45.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  135.23
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  10-(2-Ethoxy-3,4-dioxo-1-cyclobutenyl)-1,4,7,10-tetraazacyclododecan-2,4,7-triacetic acid tris(tert-butyl ester) 在 三氟乙酸 作用下， 反应 18.0h， 以95%的产率得到10-(2-Ethoxy-3,4-dioxo-1-cyclobutenyl)-1,4,7,10-tetraazacyclododecan-2,4,7-triacetic acid
  参考文献：
  名称：

  Inulin as a Carrier for Contrast Agents in Magnetic Resonance Imaging

  摘要：

  Magnetic resonance angiography (MRA) has put forth an impetus for the development of macromolecular Gd-III complexes that have a prolonged lifetime in the vascular system. Herein, we report the synthesis and Gd-III complexation of a new sugar conjugate based on inulin and the DO3A ligand (DO3A = 1,4,7,10-tetraazacyclododecan1,4,7-triacetic acid). Two API-DO3ASQ conjugates (API = 0-(aminopropyl)inulin, SQ = squaric acid = 3,4-dihydroxy-3cyclobutene-1,2-dione) with different degrees of substitution (ds=0.7 and ds=1.5) were prepared from API by using the diethyl ester of squaric acid as a linking agent for the DO3A chelate. The efficacies of the resulting Gd-III compounds were evaluated by investigation of their water H-1 longitudinal- relaxation-rate enhancements at variable field (NMRD). A dramatic increase in relaxivity was observed in the more highly substituted conjugate (ds = 1.5); this prompted us to do a variable-temperature 170 study in order to further characterize the relaxation parameters involved in this system. [Gd(APIDO3ASQ)] shows promising properties for application as a contrast agent for MRI.

  DOI：

  10.1002/1521-3765(20010105)7:1<64::aid-chem64>3.0.co;2-s
• 作为产物：
  描述：

  方酸二乙酯 、 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 三乙胺 作用下， 以 乙醇 为溶剂， 反应 96.0h， 以96%的产率得到10-(2-Ethoxy-3,4-dioxo-1-cyclobutenyl)-1,4,7,10-tetraazacyclododecan-2,4,7-triacetic acid tris(tert-butyl ester)
  参考文献：
  名称：

  Inulin as a Carrier for Contrast Agents in Magnetic Resonance Imaging

  摘要：

  Magnetic resonance angiography (MRA) has put forth an impetus for the development of macromolecular Gd-III complexes that have a prolonged lifetime in the vascular system. Herein, we report the synthesis and Gd-III complexation of a new sugar conjugate based on inulin and the DO3A ligand (DO3A = 1,4,7,10-tetraazacyclododecan1,4,7-triacetic acid). Two API-DO3ASQ conjugates (API = 0-(aminopropyl)inulin, SQ = squaric acid = 3,4-dihydroxy-3cyclobutene-1,2-dione) with different degrees of substitution (ds=0.7 and ds=1.5) were prepared from API by using the diethyl ester of squaric acid as a linking agent for the DO3A chelate. The efficacies of the resulting Gd-III compounds were evaluated by investigation of their water H-1 longitudinal- relaxation-rate enhancements at variable field (NMRD). A dramatic increase in relaxivity was observed in the more highly substituted conjugate (ds = 1.5); this prompted us to do a variable-temperature 170 study in order to further characterize the relaxation parameters involved in this system. [Gd(APIDO3ASQ)] shows promising properties for application as a contrast agent for MRI.

  DOI：

  10.1002/1521-3765(20010105)7:1<64::aid-chem64>3.0.co;2-s

文献信息

• A macromolecular Gd(III) complex as pH-responsive relaxometric probe for MRI applications
  作者：Silvio Aime、Simonetta Geninatti Crich、Mauro Botta、Giovanni Giovenzana、Giovanni Palmisano、Massimo Sisti

  DOI：10.1039/a900499h

  日期：——

  The ability of the paramagnetic macromolecular complex (GdDO3ASQ)30-Orn114 to enhance the water proton relaxation rate has been found to be a function of pH; this behaviour is related to the structural changes occurring in the polypeptide upon protonation of the side-chain NH2 groups.

  顺磁性高分子复合物（GdDO3ASQ）30-Orn114增强水质子弛豫速率的能力被发现是pH值的函数；这种行为与多肽侧链NH2基团质子化时发生的结构变化有关。