5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethylsulfanylmethyl]-thionicotinamide | 179072-18-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethylsulfanylmethyl]-thionicotinamide
• CAS: 179072-18-5
• 化学式: C₂₅H₃₀N₂OS₂Si
• 分子量: 466.743
• InChiKey: LFNNCOBKPUYGAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  48.14
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethylsulfanylmethyl]-thionicotinamide 在 氟化铵 作用下， 以 甲醇 为溶剂， 以76%的产率得到5-(2-Hydroxyethylsulfanylmethyl)pyridine-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 劳森试剂 、 咪唑 、 盐酸 、 氟化铵 、 正丁基锂 、 氯化亚砜 、 氨 、 sodium 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 13.17h， 生成 5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethylsulfanylmethyl]-thionicotinamide
  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