α-fluoromethyl-2-methyl-5-nitroimidazole-1-ethanol | 194803-27-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: α-fluoromethyl-2-methyl-5-nitroimidazole-1-ethanol
• 英文别名: α-fluoromethyl-2-methyl-5-nitroimidazol-1-ethanol；α-fluoromethyl-2-methyl-5-nitroimidazol-1-ethanol；1-(3-fluoro-2-hydroxypropyl)-2-methyl-5-nitroimidazole；1-Fluoro-3-(2-methyl-5-nitroimidazol-1-yl)propan-2-ol
• CAS: 194803-27-5
• 化学式: C₇H₁₀FN₃O₃
• 分子量: 203.173
• InChiKey: GWGDYQMWUMDHEF-UHFFFAOYSA-N

物化性质

• 沸点：
  434.6±40.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  α-fluoromethyl-2-methyl-5-nitroimidazole-1-ethanol 生成 R-(+)-1-(3-fluoro-2-hydroxypropyl)-2-methyl-5-nitroimidazole
  参考文献：
  名称：

  Lipase-catalyzed resolution of both enantiomers of Ornidazole and some analogues

  摘要：

  The resolution of the enantiomers of the chemotherapeutic Ornidazole (Tiberal((R))) 1a was achieved by acetylation of the racemic compound with vinylacetate in the presence of lipase Amano PS (from Pseudomonas cepacia). The halogen analogues 4a-6a and the corresponding 4-nitro-derivatives 1b and 4b-6b were also synthesized and the enantiomers were separated by kinetic enzymatic resolution. The absolute configuration of two compounds was determined by X-ray crystallography. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00260-7
• 作为产物：
  描述：

  奥硝唑 在 sodium hydroxide 、 pyridinium polyhydrogenfluoride 作用下， 反应 12.25h， 生成 α-fluoromethyl-2-methyl-5-nitroimidazole-1-ethanol
  参考文献：
  名称：

  Lipase-catalyzed resolution of both enantiomers of Ornidazole and some analogues

  摘要：

  The resolution of the enantiomers of the chemotherapeutic Ornidazole (Tiberal((R))) 1a was achieved by acetylation of the racemic compound with vinylacetate in the presence of lipase Amano PS (from Pseudomonas cepacia). The halogen analogues 4a-6a and the corresponding 4-nitro-derivatives 1b and 4b-6b were also synthesized and the enantiomers were separated by kinetic enzymatic resolution. The absolute configuration of two compounds was determined by X-ray crystallography. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00260-7

文献信息

• Compounds And Methods For Selective Imaging And/Or Ablation
  申请人：Auckland Uniservices Limited

  公开号：US20150010474A1

  公开（公告）日：2015-01-08

  The invention relates generally to compounds and methods for imaging and/or selective ablation of nitroreductase-expressing cells and/or biological agents. More particularly, although not exclusively, the invention provides compounds that are selectively metabolised by bacterial nitroreductases and are substantially insensitive to metabolism under oxic or hypoxic conditions by human nitroreductase enzymes.

  本发明涉及化合物和方法，用于成像和/或选择性消融硝基还原酶表达的细胞和/或生物制剂。更具体地说，虽然不仅限于此，本发明提供的化合物被细菌硝基还原酶选择性代谢，且在人类硝基还原酶酶下氧化或缺氧条件下代谢相对不敏感。