(E)-5-(2-nitroimidazolyl)-4-hydroxy-1-(tributylstannyl)pent-1-ene | 133933-38-7

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (E)-5-(2-nitroimidazolyl)-4-hydroxy-1-(tributylstannyl)pent-1-ene
• CAS: 133933-38-7
• 化学式: C₂₀H₃₇N₃O₃Sn
• 分子量: 486.242
• InChiKey: UFNFSRWSFYBPJA-HEDVWWMMSA-N

反应信息

• 作为反应物：
  描述：

  (E)-5-(2-nitroimidazolyl)-4-hydroxy-1-(tributylstannyl)pent-1-ene 在 双氧水 、 sodium acetate 、 溶剂黄146 、 sodium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以54.2%的产率得到(iodovinyl)misonidazole
  参考文献：
  名称：

  Synthesis of an (iodovinyl)misonidazole derivative for hypoxia imaging

  摘要：

  Nitroimidazoles undergo a bioreduction in viable hypoxic tissue, resulting in trapping within these tissues, as demonstrated by misonidazole. A radioiodinated analogue of misonidazole (IVM, (E)-5-(2-Nitroimidazolyl)-4-hydroxy-1-iodopent-1-ene, 3) has been synthesized by halodestannylation, for evaluation as an imaging agent for hypoxia. A key step in the synthetic sequence involves the use of the Lewis acid BF3.Et2O to promote the nucleophilic ring opening of glycidyl tosylate with (E)-1-lithio-2-(tributylstannyl)ethylene. Direct comparison of IVM versus F-MISO (2) another misonidazole type hypoxic cell marker, in several in vitro cell culture studies, indicates that IVM behaves in analogous fashion to F-MISO and has promise as a hypoxia imaging agent for SPECT.

  DOI：

  10.1021/jm00111a036