[18F]fluoromisonidazole

• 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: [18F]fluoromisonidazole
• 英文别名: (2R)-1-(18F)fluoranyl-3-(2-nitroimidazol-1-yl)propan-2-ol
• 化学式: C₆H₈FN₃O₃
• 分子量: 188.148
• InChiKey: HIIJZYSUEJYLMX-FQLBDKRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-硝基咪唑 、 [18F]epifluorohydrin 在 N,N-二异丙基乙胺 作用下， 以 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 0.25h， 生成 [18F]fluoromisonidazole
  参考文献：
  名称：

  A concise one-pot synthesis of [18F]fluoromisonidazole from (2R)-(−)-glycidyl tosylate

  摘要：

  A rapid, one-pot synthesis of [F-18]fluoromisonidazole (1H-1-(3-[F-18]fluoro-2-hydroxypropyl)-2-nitroimidazole) (1) starting from [F-18]fluoride and (2R)-(-)-glycidyl tosylate (2) is described. The total time required for the synthesis, the radiochemical yield, and purity of the titled compound are ca. 80 min, 20%, and >98%, respectively.

  DOI：

  10.1002/(sici)1099-1344(199608)38:8<771::aid-jlcr893>3.0.co;2-a

文献信息

• Co(salen)-mediated enantioselective radiofluorination of epoxides. Radiosynthesis of enantiomerically enriched [18F]F-MISO via kinetic resolution
  作者：Evgeny Revunov、Fedor Zhuravlev

  DOI：10.1016/j.jfluchem.2013.09.006

  日期：2013.12

  The first example of transition metal mediated enantioselective radiofluorination of epoxides is reported. The procedure utilizes gaseous [F-18]HF in a combination with (-)tetramisole and (R,R)-Co(salen), giving the corresponding (S,S)-F-18-fluorohydrines in 78-93% radiochemical yield (RCY) and 20-46% enantioselectivities (ee). The use of this methodology allowed for a single step radiosynthesis of [F-18]F-MISO, which took 1.5 h and after solid phase-based purification delivered [F-18]F-MISO in 81%/45% analytical/preparative RCY and 55% ee. (C) 2013 Elsevier B.V. All rights reserved.
• A concise one-pot synthesis of [18F]fluoromisonidazole from (2R)-(−)-glycidyl tosylate
  作者：Masao Tada、Ren Iwata、Hiroshi Sugiyama、Kazunori Sato、Kazuo Kubota、Roko Kubota、Hiromu Takahashi、Hiroshi Fukuda、Tatsuo Ido

  DOI：10.1002/(sici)1099-1344(199608)38:8<771::aid-jlcr893>3.0.co;2-a

  日期：1996.8

  A rapid, one-pot synthesis of [F-18]fluoromisonidazole (1H-1-(3-[F-18]fluoro-2-hydroxypropyl)-2-nitroimidazole) (1) starting from [F-18]fluoride and (2R)-(-)-glycidyl tosylate (2) is described. The total time required for the synthesis, the radiochemical yield, and purity of the titled compound are ca. 80 min, 20%, and >98%, respectively.