12-(4-Bromobenzyloxy)-3,6,9-tris(2-nitrobenzenesulfonyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene | 227457-58-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 12-(4-Bromobenzyloxy)-3,6,9-tris(2-nitrobenzenesulfonyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene
• CAS: 227457-58-1
• 化学式: C₃₆H₃₂BrN₇O₁₃S₃
• 分子量: 946.791
• InChiKey: SGTFPHJRPSPYMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  60.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  263.68
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  12-(4-Bromobenzyloxy)-3,6,9-tris(2-nitrobenzenesulfonyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene 在 lithium hydroxide 、 水 、 巯基乙酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 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-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：

  邻硝基苯磺酰氯 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 8.0h， 生成 12-(4-Bromobenzyloxy)-3,6,9-tris(2-nitrobenzenesulfonyl)-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