3-bromo-5-(2-hydroxyethoxymethyl)pyridine-1-oxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-bromo-5-(2-hydroxyethoxymethyl)pyridine-1-oxide
• 英文别名: 2-[(5-Bromo-1-oxidopyridin-1-ium-3-yl)methoxy]ethanol
• 化学式: C₈H₁₀BrNO₃
• 分子量: 248.076
• InChiKey: BYSOOOGCTMYONP-UHFFFAOYSA-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：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-溴-5-氯甲基吡啶盐酸盐 在 双氧水 、 乙二醇 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 反应 28.0h， 生成 3-bromo-5-(2-hydroxyethoxymethyl)pyridine-1-oxide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Some Acyclic Pyridine C-Nucleosides. Part One

  摘要：

  The reaction between 3-bromo-5-chloromethylpyridine hydrochloride (($) under bar 4) with the mono sodium salt of ethylene glycol was investigated. 3-Bromo-5-(2-hydroxyethoxymethyl) pyridine (($) under bar 5) was synthesized and converted to the 3-carboxy analogue using butyllithium and CO,. Subsequent treatment with diazomethane and ammonolysis gave the corresponding acyclic nicotinamide C-nucleosides. The latter compounds were converted into the thioamide analogues by reaction with Lawesson's reagent. The pyridine N-oxide derivatives were obtained by treatment with peracetic acid or hydrogen peroxide. Ah compounds were identified with the aid of H-1- and C-13-NMR and mass spectrometry. The acyclic pyridine C-nucleosides were evaluated against a number of viral strains and cancer cell lines but no significant biological activity was found.

  DOI：

  10.1080/15257779408013225

文献信息

• Synthesis and Biological Evaluation of Some Acyclic Pyridine C-Nucleosides. Part One
  作者：J. Van Hemel、E. L. Esmans、F. C. Alderweireldt、R. A. Dommisse、A. De Groot、J. Balzarini、E. De Clercq

  DOI：10.1080/15257779408013225

  日期：1994.12

  The reaction between 3-bromo-5-chloromethylpyridine hydrochloride (($) under bar 4) with the mono sodium salt of ethylene glycol was investigated. 3-Bromo-5-(2-hydroxyethoxymethyl) pyridine (($) under bar 5) was synthesized and converted to the 3-carboxy analogue using butyllithium and CO,. Subsequent treatment with diazomethane and ammonolysis gave the corresponding acyclic nicotinamide C-nucleosides. The latter compounds were converted into the thioamide analogues by reaction with Lawesson's reagent. The pyridine N-oxide derivatives were obtained by treatment with peracetic acid or hydrogen peroxide. Ah compounds were identified with the aid of H-1- and C-13-NMR and mass spectrometry. The acyclic pyridine C-nucleosides were evaluated against a number of viral strains and cancer cell lines but no significant biological activity was found.