12-(4-Bromobenzyloxy)-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene | 227457-59-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 12-(4-Bromobenzyloxy)-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene
• 英文别名: 12-[(4-Bromophenyl)methoxy]-3,6,9,15-tetrazabicyclo[9.3.1]pentadeca-1(15),11,13-triene
• CAS: 227457-59-2
• 化学式: C₁₈H₂₃BrN₄O
• 分子量: 391.311
• InChiKey: IQZAJVTUTLYVEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  58.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  potassium chloroacetate 、 12-(4-Bromobenzyloxy)-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene 在 水 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 12-(4-Bromobenzyloxy)-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene-3,6,9-triacetic acid
  参考文献：
  名称：

  Contrast Agents for Magnetic Resonance Imaging: A Novel Route to Enhanced Relaxivities Based on the Interaction of a GdIII Chelate with Poly-β-cyclodextrins

  摘要：

  This study proposes a novel route to improved contrast agents for magnetic resonance imaging (MRI) applications based on the formation of a non-covalent adduct between a paramagnetic complex and an exogeneous macromolecule. For this purpose a 12-membered pyridine-containing triacetate macrocyclic ligand with a p-bromo-benzyloxy substituent on the pyridine moiety was synthesized. The Gd-III complex containing this ligand shows a relaxivity of 8.25 mM(-1)s(-1) at 20 MHz and 25 degrees C The hydrophobic p-bromo-benzyloxy moiety promotes the interaction of the chelate with human serum albumin (HSA) (K-a = 4 x 10(2) M-1) and with beta-cyclodextrin (K-a = 8 x 10(2) M-1). Upon replacing beta-cyclodextrin with a poly-beta-cyclodextrin substrate (MW = ca. 6000 Da) a further relaxation enhancement is detected as a consequence of the increased molecular size of the resulting inclusion compound. In a typical experiment in blood serum, the observed relaxivity is 32 mM(-1) s(-1) (20 MHz, 25 degrees C) when the concentrations are as follows: Gd-III chelate 1 mM, poly-beta-cyclodextrin 10 mM, HSA 0.58 mM. Under these conditions the Gd-III chelate is mainly present as an inclusion compound with the poly-beta-CD. This finding suggests a potential use for such a Gd-III chelate/poly-beta-CD system in MR angiographic applications.

  DOI：

  10.1002/(sici)1521-3765(19990401)5:4<1253::aid-chem1253>3.0.co;2-i
• 作为产物：
  描述：

  3-羟基-2,6-双(羟甲基)吡啶盐酸盐 在 四氯化碳 、 lithium hydroxide 、 三丁基膦 、 potassium carbonate 、 巯基乙酸 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 21.0h， 生成 12-(4-Bromobenzyloxy)-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene
  参考文献：
  名称：

  Contrast Agents for Magnetic Resonance Imaging: A Novel Route to Enhanced Relaxivities Based on the Interaction of a GdIII Chelate with Poly-β-cyclodextrins

  摘要：

  This study proposes a novel route to improved contrast agents for magnetic resonance imaging (MRI) applications based on the formation of a non-covalent adduct between a paramagnetic complex and an exogeneous macromolecule. For this purpose a 12-membered pyridine-containing triacetate macrocyclic ligand with a p-bromo-benzyloxy substituent on the pyridine moiety was synthesized. The Gd-III complex containing this ligand shows a relaxivity of 8.25 mM(-1)s(-1) at 20 MHz and 25 degrees C The hydrophobic p-bromo-benzyloxy moiety promotes the interaction of the chelate with human serum albumin (HSA) (K-a = 4 x 10(2) M-1) and with beta-cyclodextrin (K-a = 8 x 10(2) M-1). Upon replacing beta-cyclodextrin with a poly-beta-cyclodextrin substrate (MW = ca. 6000 Da) a further relaxation enhancement is detected as a consequence of the increased molecular size of the resulting inclusion compound. In a typical experiment in blood serum, the observed relaxivity is 32 mM(-1) s(-1) (20 MHz, 25 degrees C) when the concentrations are as follows: Gd-III chelate 1 mM, poly-beta-cyclodextrin 10 mM, HSA 0.58 mM. Under these conditions the Gd-III chelate is mainly present as an inclusion compound with the poly-beta-CD. This finding suggests a potential use for such a Gd-III chelate/poly-beta-CD system in MR angiographic applications.

  DOI：

  10.1002/(sici)1521-3765(19990401)5:4<1253::aid-chem1253>3.0.co;2-i

文献信息

• Diethoxyphosphoryl as a Protecting-Activating Group in the Synthesis of Polyazacyclophanes
  作者：Andrea Chellini、Roberto Pagliarin、Giovanni B. Giovenzana、Giovanni Palmisano、Massimo Sisti

  DOI：10.1002/(sici)1522-2675(20000412)83:4<793::aid-hlca793>3.0.co;2-3

  日期：2000.4.12

  The fully diethoxyphosphoryl(Dep)-protected polyamines 1b-3b were prepared from the corresponding polyamines with 'diethyl phosphite' (= diethyl phosphonate) and CCl4 in a solid base/organic liquid two-phase system in the presence of Bu4NBr as phase-transfer catalyst. Subsequent phase-transfer-catalyzed alkylation of phosphoramidates 1b-3b with bis(chloromethyl)arenes 5-8 in the presence of Bu4N(HSO4) followed by deprotection gave good yields of polyazacyclophanes 9a-16a.