diethyl 2-(3-(2-nitro-1H-imidazol-1-yl)-2-hydroxypropyl)malonate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: diethyl 2-(3-(2-nitro-1H-imidazol-1-yl)-2-hydroxypropyl)malonate
• 英文别名: Diethyl 2-[2-hydroxy-3-(2-nitroimidazol-1-yl)propyl]propanedioate
• 化学式: C₁₃H₁₉N₃O₇
• 分子量: 329.31
• InChiKey: DMDYTNUXAOGWGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  烯丙基丙二酸二乙酯 在 Proton Sponge 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 diethyl 2-(3-(2-nitro-1H-imidazol-1-yl)-2-hydroxypropyl)malonate
  参考文献：
  名称：

  The Synthesis and in vitro Evaluation of a 99mTechnetium-Nitroimidazole Complex Based on a Bis(amine-phenol) Ligand: Comparison to BMS-181321

  摘要：

  We have developed a (99m)Technetium complex for imaging of hypoxic tissue (BMS-181321). Recently, another nitroimidazole derivative, based upon a bis(amine-phenol) ligand, was described in the patent literature. To compare this compound to BMS-181321, we have synthesized the ligand, prepared its Tc-99m complex, and evaluated its performance in two in vitro assays of bioefficacy: membrane permeability and uptake in normoxic and anoxic cardiocytes. In attempting to reproduce the synthesis of the ligand described in the patent application, we found that one intermediate could not be made by the method described, and alternative routes were investigated. Complexation of the bis(amine-phenol) nitroimidazole with Tc-99m gave an apparent single complex; this appeared as a broad peak on HPLC analysis. Purification by a solid-phase method gave a complex with 95% radiochemical purity. This complex was not permeable to cultured bovine brain endothelial cells nor did it show preferential uptake in anoxic myocytes.

  DOI：

  10.1021/jm00050a012