Tert-butyl 2-[4-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-7-[2-(2-nitroimidazol-1-yl)ethyl]-1,4,7-triazonan-1-yl]acetate | 1372398-75-8

• 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: Tert-butyl 2-[4-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-7-[2-(2-nitroimidazol-1-yl)ethyl]-1,4,7-triazonan-1-yl]acetate
• CAS: 1372398-75-8
• 化学式: C₂₃H₄₀N₆O₆
• 分子量: 496.607
• InChiKey: VUKNEZUHCNKQCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Tert-butyl 2-[4-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-7-[2-(2-nitroimidazol-1-yl)ethyl]-1,4,7-triazonan-1-yl]acetate 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 15.0h， 以85%的产率得到2-[4-(Carboxymethyl)-7-[2-(2-nitroimidazol-1-yl)ethyl]-1,4,7-triazonan-1-yl]acetic acid
  参考文献：
  名称：

  Syntheses of 2-Nitroimidazole Derivatives Conjugated with 1,4,7-Triazacyclononane-N,N′-Diacetic Acid Labeled with F-18 Using an Aluminum Complex Method for Hypoxia Imaging

  摘要：

  Hypoxia imaging is important for diagnosis of ischemic diseases, and thus various F-18-labeled radiopharmaceuticals have been developed. However, F-18-labeling requires multistep procedures including azeotropic distillation, which is complicated and difficult to automate. Recently, F-18-labeling method using Al-F complex in aqueous solution was devised that offered a straightforward F-18-labeling procedure. We synthesized nitroimidazole derivatives conjugated with 1,4,7-triazacyclononane-1,4-diacetic acid (NODA) that can be labeled with F-18 using Al-F complex and examined their radiochemistries, in vitro and in vivo biological properties, and animal PET imaging characteristics. We found that the synthesized derivatives have excellent F-18-labeling efficiencies, high stabilities, specific uptakes in cultured hypoxic tumor cells, and high tumor to nontumor ratios in xenografted mice. Furthermore, the derivatives were labeled with F-18 in a straightforward manner within 15 min at high labeling efficiencies and radiochemical purities. In conclusion, F-18-labeled NODA-nitroimidazole conjugates were developed and proved to be promising hypoxia PET agents.

  DOI：

  10.1021/jm201611a
• 作为产物：
  描述：

  1-(2-溴乙基)-2-硝基-1H-咪唑 、 1,4,7-三氮杂环壬烷-1,4-二乙酸二叔丁酯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以63%的产率得到Tert-butyl 2-[4-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-7-[2-(2-nitroimidazol-1-yl)ethyl]-1,4,7-triazonan-1-yl]acetate
  参考文献：
  名称：

  Syntheses of 2-Nitroimidazole Derivatives Conjugated with 1,4,7-Triazacyclononane-N,N′-Diacetic Acid Labeled with F-18 Using an Aluminum Complex Method for Hypoxia Imaging

  摘要：

  Hypoxia imaging is important for diagnosis of ischemic diseases, and thus various F-18-labeled radiopharmaceuticals have been developed. However, F-18-labeling requires multistep procedures including azeotropic distillation, which is complicated and difficult to automate. Recently, F-18-labeling method using Al-F complex in aqueous solution was devised that offered a straightforward F-18-labeling procedure. We synthesized nitroimidazole derivatives conjugated with 1,4,7-triazacyclononane-1,4-diacetic acid (NODA) that can be labeled with F-18 using Al-F complex and examined their radiochemistries, in vitro and in vivo biological properties, and animal PET imaging characteristics. We found that the synthesized derivatives have excellent F-18-labeling efficiencies, high stabilities, specific uptakes in cultured hypoxic tumor cells, and high tumor to nontumor ratios in xenografted mice. Furthermore, the derivatives were labeled with F-18 in a straightforward manner within 15 min at high labeling efficiencies and radiochemical purities. In conclusion, F-18-labeled NODA-nitroimidazole conjugates were developed and proved to be promising hypoxia PET agents.

  DOI：

  10.1021/jm201611a