8-Iodo-6-methyl-3-(phenethylsulfanylmethyl)imidazo[1,2-a]pyridine | 955942-07-1

• 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-Iodo-6-methyl-3-(phenethylsulfanylmethyl)imidazo[1,2-a]pyridine
• 英文别名: 8-iodo-6-methyl-3-(2-phenylethylsulfanylmethyl)imidazo[1,2-a]pyridine
• CAS: 955942-07-1
• 化学式: C₁₇H₁₇IN₂S
• 分子量: 408.306
• InChiKey: ACTVUNQBPXQVIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  42.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-Iodo-6-methyl-3-(phenethylsulfanylmethyl)imidazo[1,2-a]pyridine 、 4-羟基苯硫酚 在 copper(l) iodide 、 potassium carbonate 、 乙二醇 作用下， 以 异丙醇 为溶剂， 反应 48.0h， 以21%的产率得到8-(4-hydroxyphenylthio)-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
• 作为产物：
  描述：

  2-苯乙硫醇 、 3-hydroxymethyl-8-iodo-6-methylimidazo[1,2-a]pyridine 在 溶剂黄146 作用下， 以78%的产率得到8-Iodo-6-methyl-3-(phenethylsulfanylmethyl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

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

  摘要：

  The synthesis of original imidazo[1,2-a]pyridines bearing a phenethylthiomethyl side chain at the 3 position and a (hetero)aryl substituent on the 6 or 8 position, and their antiviral activities are reported. From the synthesized compounds, the 6-halogeno and 6-phenylimidazo[1,2-a]pyridine derivatives 4c-d and 5b were the most potent against human cytomegalovirus (CMV) and/ or varicella-zoster virus (VZV), whereas several other congeners (i.e., 5e, 5g, 5i, 5l, 5n, 5p, 5q, and 5t), while less potent, were equally or more selective in their inhibitory activity against both 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) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2007.03.061

文献信息

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

  DOI：10.1016/j.bmc.2007.03.061

  日期：2007.11

  The synthesis of original imidazo[1,2-a]pyridines bearing a phenethylthiomethyl side chain at the 3 position and a (hetero)aryl substituent on the 6 or 8 position, and their antiviral activities are reported. From the synthesized compounds, the 6-halogeno and 6-phenylimidazo[1,2-a]pyridine derivatives 4c-d and 5b were the most potent against human cytomegalovirus (CMV) and/ or varicella-zoster virus (VZV), whereas several other congeners (i.e., 5e, 5g, 5i, 5l, 5n, 5p, 5q, and 5t), while less potent, were equally or more selective in their inhibitory activity against both 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) 2007 Published by Elsevier Ltd.
• 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.