3-bromo-5-(2-hydroxyethoxymethyl)pyridine | 166094-19-5

• 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
• 英文别名: 2-[(5-Bromopyridin-3-yl)methoxy]ethanol
• CAS: 166094-19-5
• 化学式: C₈H₁₀BrNO₂
• 分子量: 232.077
• InChiKey: NVSZEHBGHHANPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 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：
  42.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromo-5-(2-hydroxyethoxymethyl)pyridine 在 咪唑 、 正丁基锂 、 氨 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.08h， 生成 3-carbamoyl-5-(2-tert-butyldiphenylsilyloxyethoxymethyl)pyridine
  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
• 作为产物：
  描述：

  5-溴烟酸甲酯 在 盐酸 、 sodium tetrahydroborate 、 氯化亚砜 、 乙二醇 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 40.08h， 生成 3-bromo-5-(2-hydroxyethoxymethyl)pyridine
  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 Phosphonate Derivatives of Some Acyclic Pyridine-C-Nucleosides
  作者：Johan Van hemel、Eddy L. Esmans、Pieter E. Joos、Alex De Groot、Roger A. Dommisse、Jan M. Balzarini、Erik D. De Clercq

  DOI：10.1080/07328319808004329

  日期：1998.12

  The synthesis of phosphonomethoxy derivatives of some acyclic pyridine-C-nucleosides is described. Reaction of the acyclic nucleoside alkoxides with diethyl (tosyloxymethyl)phosphonate (5) led to the protected phosphonate derivatives. After eventual modification of the pyridine moiety, the ethyl protecting groups could be removed by treatment with bromotrimethylsilane. The phosphonates were evaluated against a series of tumor cell lines and a variety of viruses. Compared to the nucleoside analogues, they showed a slightly higher activity.