2,2'-(iminodi-6,1-hexanediyl)bis-1H-isoindole-1,3(2H)-dione | 1201807-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2,2'-(iminodi-6,1-hexanediyl)bis-1H-isoindole-1,3(2H)-dione
• 英文别名: 2-[6-[6-(1,3-Dioxoisoindol-2-yl)hexylamino]hexyl]isoindole-1,3-dione
• CAS: 1201807-19-3
• 化学式: C₂₈H₃₃N₃O₄
• 分子量: 475.588
• InChiKey: RCCDYBUCIZBDAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  86.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  溴乙酸乙酯 、 2,2'-(iminodi-6,1-hexanediyl)bis-1H-isoindole-1,3(2H)-dione 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 以150 mg的产率得到N,N-bis[6-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)hexyl]glycine ethyl ester
  参考文献：
  名称：

  Biotin Derivatives Carrying Two Chelating DOTA Units. Synthesis, in Vitro Evaluation of Biotinidases Resistance, Avidin Binding, and Radiolabeling Tests

  摘要：

  The synthesis of four biotin derivatives carrying two DOTA moieties for each ligand (BisDOTA set) is reported, for increasing radiation/dose ratio and improving efficiency in the pretargeted avidin-biotin radioimmunotherapy. The biotin-containing scaffold of two BisDOTA was similar to the mono-DOTA derivative previously described. Then the scaffold was elongated by trifunctionalized spacers of different length and conjugated with one of the COOH groups of two DOTA. Two others were prepared starting from a on-resin lysine residue. The lysine alpha-NH2 was bonded to blotin, and then spacers were appended to the alpha-NH2 and conjugated with two DOTA molecules. One compound contairted a p-aminoberizoic acid spacer, which ensured higher head-to-tail distance and increased rigidity ofthe chain. These last two compounds had a very high ability to bond avidin and were labeled with Y-90 at high specific activity. All the compOLInds were resistant to the action of'scrurn biotinidases.

  DOI：

  10.1021/jm9014372
• 作为产物：
  描述：

  苯酐 、 双(六亚甲基)三胺 以 甲苯 为溶剂， 反应 8.0h， 生成 2,2'-(iminodi-6,1-hexanediyl)bis-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Biotin Derivatives Carrying Two Chelating DOTA Units. Synthesis, in Vitro Evaluation of Biotinidases Resistance, Avidin Binding, and Radiolabeling Tests

  摘要：

  The synthesis of four biotin derivatives carrying two DOTA moieties for each ligand (BisDOTA set) is reported, for increasing radiation/dose ratio and improving efficiency in the pretargeted avidin-biotin radioimmunotherapy. The biotin-containing scaffold of two BisDOTA was similar to the mono-DOTA derivative previously described. Then the scaffold was elongated by trifunctionalized spacers of different length and conjugated with one of the COOH groups of two DOTA. Two others were prepared starting from a on-resin lysine residue. The lysine alpha-NH2 was bonded to blotin, and then spacers were appended to the alpha-NH2 and conjugated with two DOTA molecules. One compound contairted a p-aminoberizoic acid spacer, which ensured higher head-to-tail distance and increased rigidity ofthe chain. These last two compounds had a very high ability to bond avidin and were labeled with Y-90 at high specific activity. All the compOLInds were resistant to the action of'scrurn biotinidases.

  DOI：

  10.1021/jm9014372

文献信息

• Biotin Derivatives Carrying Two Chelating DOTA Units. Synthesis, in Vitro Evaluation of Biotinidases Resistance, Avidin Binding, and Radiolabeling Tests
  作者：Alessandro Pratesi、Francesca Bucelli、Ilaria Mori、Marco Chinol、Antonio Verdoliva、Giovanni Paganelli、Vincenzo Rivieccio、Lucia Gariboldi、Mauro Ginanneschi

  DOI：10.1021/jm9014372

  日期：2010.1.14

  The synthesis of four biotin derivatives carrying two DOTA moieties for each ligand (BisDOTA set) is reported, for increasing radiation/dose ratio and improving efficiency in the pretargeted avidin-biotin radioimmunotherapy. The biotin-containing scaffold of two BisDOTA was similar to the mono-DOTA derivative previously described. Then the scaffold was elongated by trifunctionalized spacers of different length and conjugated with one of the COOH groups of two DOTA. Two others were prepared starting from a on-resin lysine residue. The lysine alpha-NH2 was bonded to blotin, and then spacers were appended to the alpha-NH2 and conjugated with two DOTA molecules. One compound contairted a p-aminoberizoic acid spacer, which ensured higher head-to-tail distance and increased rigidity ofthe chain. These last two compounds had a very high ability to bond avidin and were labeled with Y-90 at high specific activity. All the compOLInds were resistant to the action of'scrurn biotinidases.