[6-氨基-2,4,5,7-四溴-9-(2-甲氧羰基苯基)氧杂蒽-3-亚基]氯化铵 | 208511-49-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: [6-氨基-2,4,5,7-四溴-9-(2-甲氧羰基苯基)氧杂蒽-3-亚基]氯化铵
• 英文名称: 2-(6-Amino-2,4,5,7-tetrabromo-3-imino-3H-xanthen-9-yl)-benzoic acid methyl ester; hydrochloride
• 英文别名: Methyl 2-(3-amino-2,4,5,7-tetrabromo-6-iminoxanthen-9-yl)benzoate;hydrochloride；methyl 2-(3-amino-2,4,5,7-tetrabromo-6-iminoxanthen-9-yl)benzoate;hydrochloride
• CAS: 208511-49-3
• 化学式: C₂₁H₁₂Br₄N₂O₃*ClH
• 分子量: 696.415
• InChiKey: GMCVSEFMPYGLOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  rhodamin 123 在 溴 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以56.45%的产率得到[6-氨基-2,4,5,7-四溴-9-(2-甲氧羰基苯基)氧杂蒽-3-亚基]氯化铵
  参考文献：
  名称：

  [¹²⁵I/¹²⁷I/¹³¹I]Iodorhodamine:  Synthesis, Cellular Localization, and Biodistribution in Athymic Mice Bearing Human Tumor Xenografts and Comparison with [^99mTc]Hexakis(2-methoxyisobutylisonitrile)

  摘要：

  The synthesis of halogenated rhodamine (Rh) derivatives was carried out by controlling the stoichiometry of the halogenating agents, bromine and iodine monochloride. In the no-carrier-added synthesis of radioiodinated rhodamine 123, direct labeling of rhodamine 123 (Rh 123) with (NaI)-I-125/(NaI)-I-131 required the presence of the oxidant peracetic acid. I-125/I-131-Rh 123 was synthesized in modest yields (40-45%). HPLC purification separated Rh 123 from its mono-and diiodo derivatives. Monohalogenation of Rh 123 did not alter the compound's ability to permeate viable cells and localize in mitochondria. I-125/I-131-Rh 123 was stable in serum in vitro but rapidly metabolized after intravenous injection into mice. Consequently, scintigraphy and biodistribution data reveal poor targeting of subcutaneously growing human tumor xenografts. The results are compared to those obtained following the administration of [Tc-98m]hexakis(2-methoxyisobutylisonitrile) which also did not image human tumor xenografts in nude mice.

  DOI：

  10.1021/jm970691i