Methyl 5-[[(2-hydroxyethyl)thio]methyl]-3-pyridinecarboxylate | 179072-15-2

• 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: Methyl 5-[[(2-hydroxyethyl)thio]methyl]-3-pyridinecarboxylate
• 英文别名: methyl 5-(2-hydroxyethylsulfanylmethyl)pyridine-3-carboxylate
• CAS: 179072-15-2
• 化学式: C₁₀H₁₃NO₃S
• 分子量: 227.284
• InChiKey: AOSDCNMYLYCMRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  59.42
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Methyl 5-[[(2-hydroxyethyl)thio]methyl]-3-pyridinecarboxylate 在 劳森试剂 、 咪唑 、 氟化铵 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 8.0h， 生成 5-(2-hydroxyethylsulfanylmethyl)-N,N-dimethylpyridine-3-carbothioamide
  参考文献：
  名称：

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

  摘要：

  3-Bromo-5-(2-hydroxyethylthiomethyl)pyridine ((7) under bar) was synthesized by reaction of 3-bromo-5-chloromethylpyridine hydrochloride ((6) under bar) with the mono sodium salt of 2-mercaptoethanol. 3-Bromo-5-hydroxymethylpyridine (<(10)under bar>) was, after protection as a silyl ether, converted to the 3-carboxy analogue using BuLi and CO2. After deprotection with NH4F, the alcohol function was chlorinated using SOCl2. Finally, attachment of the acyclic chain and ammonolysis gave the acyclic nicotinamide nucleosides. Treatment of the latter compounds with Lawesson's reagent gave the thioamide analogues. All compounds were identified by NMR and DCI-MS. The acyclic pyridine C-nucleosides were evaluated against a series of tumor-cell lines and a variety of viruses. No marked biological activity was found.

  DOI：

  10.1080/07328319608007388
• 作为产物：
  描述：

  吡啶,3-溴-5-[[[(1,1-二甲基乙基)二苯基甲硅烷基]氧代]甲基]- 在 盐酸 、 氟化铵 、 正丁基锂 、 氯化亚砜 、 sodium 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 5.17h， 生成 Methyl 5-[[(2-hydroxyethyl)thio]methyl]-3-pyridinecarboxylate
  参考文献：
  名称：

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

  摘要：

  3-Bromo-5-(2-hydroxyethylthiomethyl)pyridine ((7) under bar) was synthesized by reaction of 3-bromo-5-chloromethylpyridine hydrochloride ((6) under bar) with the mono sodium salt of 2-mercaptoethanol. 3-Bromo-5-hydroxymethylpyridine (<(10)under bar>) was, after protection as a silyl ether, converted to the 3-carboxy analogue using BuLi and CO2. After deprotection with NH4F, the alcohol function was chlorinated using SOCl2. Finally, attachment of the acyclic chain and ammonolysis gave the acyclic nicotinamide nucleosides. Treatment of the latter compounds with Lawesson's reagent gave the thioamide analogues. All compounds were identified by NMR and DCI-MS. The acyclic pyridine C-nucleosides were evaluated against a series of tumor-cell lines and a variety of viruses. No marked biological activity was found.

  DOI：

  10.1080/07328319608007388

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.