8-cyano-6-methyl-3-phenethylthiomethylimidazo[1,2-a]pyridine | 1076691-35-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 8-cyano-6-methyl-3-phenethylthiomethylimidazo[1,2-a]pyridine
• 英文别名: 6-Methyl-3-(2-phenylethylsulfanylmethyl)imidazo[1,2-a]pyridine-8-carbonitrile
• CAS: 1076691-35-4
• 化学式: C₁₈H₁₇N₃S
• 分子量: 307.419
• InChiKey: IWKYBJJKNKOTKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  sodium cyanide 、 8-Iodo-6-methyl-3-(phenethylsulfanylmethyl)imidazo[1,2-a]pyridine 在 copper(l) iodide 、 N,N'-二甲基乙二胺 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以94%的产率得到8-cyano-6-methyl-3-phenethylthiomethylimidazo[1,2-a]pyridine
  参考文献：
  名称：

  Influence of 6- or 8-substitution on the antiviral activity of 3-arylalkylthiomethylimidazo[1,2-a]pyridine against human cytomegalovirus (CMV) and varicella-zoster virus (VZV): Part II

  摘要：

  The synthesis of original imidazo[1,2-a]pyridines bearing a thioether side chain at the 3 position and diversely substituted on the 6 or 8 position, and their antiviral activities are reported. From the synthesized compounds, the imidazo[1,2-a]pyridines bearing a 5 membered heterocycle (thiophene, furane or pyrrole) in the 6 position or a phenylthio group in the 6 or 8 position (14, 16, 21, 28, 45) were the most potent against human cytomegalovirus (CMV) and varicella-zoster virus (VZV), whereas several other congeners (i. e., 22, 29 and 39), while less potent, were more selective in their inhibitory activity against VZV and CMV. These compounds showed similar activity against thymidine kinase competent (TK+) and deficient (TK ) VZV strains, demonstrating a mechanism of action independent of the viral thymidine kinase. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.027

文献信息

• Influence of 6- or 8-substitution on the antiviral activity of 3-arylalkylthiomethylimidazo[1,2-a]pyridine against human cytomegalovirus (CMV) and varicella-zoster virus (VZV): Part II
  作者：Jean-Baptiste Véron、Hassan Allouchi、Cécile Enguehard-Gueiffier、Robert Snoeck、Graciela Andrei、Erik De Clercq、Alain Gueiffier

  DOI：10.1016/j.bmc.2008.09.027

  日期：2008.11

  The synthesis of original imidazo[1,2-a]pyridines bearing a thioether side chain at the 3 position and diversely substituted on the 6 or 8 position, and their antiviral activities are reported. From the synthesized compounds, the imidazo[1,2-a]pyridines bearing a 5 membered heterocycle (thiophene, furane or pyrrole) in the 6 position or a phenylthio group in the 6 or 8 position (14, 16, 21, 28, 45) were the most potent against human cytomegalovirus (CMV) and varicella-zoster virus (VZV), whereas several other congeners (i. e., 22, 29 and 39), while less potent, were more selective in their inhibitory activity against VZV and CMV. These compounds showed similar activity against thymidine kinase competent (TK+) and deficient (TK ) VZV strains, demonstrating a mechanism of action independent of the viral thymidine kinase. (C) 2008 Elsevier Ltd. All rights reserved.