7-iodo-1,3-dihydro-1-methyl-5-(4-chlorophenyl)-2H-1,4-benzodiazepin-2-one | 116725-45-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 7-iodo-1,3-dihydro-1-methyl-5-(4-chlorophenyl)-2H-1,4-benzodiazepin-2-one
• 英文别名: 5-(4-Chloro-phenyl)-7-iodo-1-methyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one；5-(4-chlorophenyl)-7-iodo-1-methyl-3H-1,4-benzodiazepin-2-one
• CAS: 116725-45-2
• 化学式: C₁₆H₁₂ClIN₂O
• 分子量: 410.642
• InChiKey: IBFFEPIOPMQPGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-iodo-1,3-dihydro-1-methyl-5-(4-chlorophenyl)-2H-1,4-benzodiazepin-2-one 在 硫酸氢铵 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 0.5h， 生成 5-(4-chlorophenyl)-7-(125I)iodanyl-1-methyl-3H-1,4-benzodiazepin-2-one
  参考文献：
  名称：

  Radioiodinated benzodiazepines: agents for mapping glial tumors

  摘要：

  Two isomeric iodinated analogues of the peripheral benzodiazepine binding site (PBS) ligand Ro5-4864 have been synthesized and labeled in high specific activity with iodine-125. Competitive binding assays conducted with the unlabeled analogues indicate high affinity for PBS. Tissue biodistribution studies in rats with these 125I-labeled ligands indicate high uptake of radioactivity in the adrenals, heart, and kidney--tissues known to have high concentrations of PBS. Preadministration of the potent PBS antagonist PK 11195 blocked in vivo uptake in adrenal tissue by over 75%, but to a lesser degree in other normal tissues. In vivo binding autoradiography in brain conducted in C6 glioma bearing rats showed dense, PBS-mediated accumulation of radioactivity in the tumor. Ligand 6 labeled with 123I may have potential for scintigraphic localization of intracranial glioma.

  DOI：

  10.1021/jm00119a005
• 作为产物：
  描述：

  5-iodo-2-amino-4'-chlorobenzophenone 在 sodium hydride 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 7-iodo-1,3-dihydro-1-methyl-5-(4-chlorophenyl)-2H-1,4-benzodiazepin-2-one
  参考文献：
  名称：

  Radioiodinated benzodiazepines: agents for mapping glial tumors

  摘要：

  Two isomeric iodinated analogues of the peripheral benzodiazepine binding site (PBS) ligand Ro5-4864 have been synthesized and labeled in high specific activity with iodine-125. Competitive binding assays conducted with the unlabeled analogues indicate high affinity for PBS. Tissue biodistribution studies in rats with these 125I-labeled ligands indicate high uptake of radioactivity in the adrenals, heart, and kidney--tissues known to have high concentrations of PBS. Preadministration of the potent PBS antagonist PK 11195 blocked in vivo uptake in adrenal tissue by over 75%, but to a lesser degree in other normal tissues. In vivo binding autoradiography in brain conducted in C6 glioma bearing rats showed dense, PBS-mediated accumulation of radioactivity in the tumor. Ligand 6 labeled with 123I may have potential for scintigraphic localization of intracranial glioma.

  DOI：

  10.1021/jm00119a005

文献信息

• VAN, DORT MARCIAN E.;CILIAX, BRIAN J.;GILDERSLEEVE, DAVID L.;SHERMAN, PHI+, J. MED. CHEM., 31,(1988) N 11, C. 2081-2086
  作者：VAN, DORT MARCIAN E.、CILIAX, BRIAN J.、GILDERSLEEVE, DAVID L.、SHERMAN, PHI+

  DOI：——

  日期：——
• Radioiodinated benzodiazepines: agents for mapping glial tumors
  作者：Marcian E. Van Dort、Brian J. Ciliax、David L. Gildersleeve、Philip S. Sherman、Karen C. Rosenspire、Anne B. Young、Larry Junck、Donald M. Wieland

  DOI：10.1021/jm00119a005

  日期：1988.11

  Two isomeric iodinated analogues of the peripheral benzodiazepine binding site (PBS) ligand Ro5-4864 have been synthesized and labeled in high specific activity with iodine-125. Competitive binding assays conducted with the unlabeled analogues indicate high affinity for PBS. Tissue biodistribution studies in rats with these 125I-labeled ligands indicate high uptake of radioactivity in the adrenals, heart, and kidney--tissues known to have high concentrations of PBS. Preadministration of the potent PBS antagonist PK 11195 blocked in vivo uptake in adrenal tissue by over 75%, but to a lesser degree in other normal tissues. In vivo binding autoradiography in brain conducted in C6 glioma bearing rats showed dense, PBS-mediated accumulation of radioactivity in the tumor. Ligand 6 labeled with 123I may have potential for scintigraphic localization of intracranial glioma.