(5Z)-2-ethylsulfanyl-3-butyl-5-(4-phenylmethyloxybenzylidene)-3,5-dihydro-4H-imidazol-4-one | 1416577-12-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (5Z)-2-ethylsulfanyl-3-butyl-5-(4-phenylmethyloxybenzylidene)-3,5-dihydro-4H-imidazol-4-one
• 英文别名: (5Z)-3-butyl-2-ethylsulfanyl-5-[(4-phenylmethoxyphenyl)methylidene]imidazol-4-one
• CAS: 1416577-12-2
• 化学式: C₂₃H₂₆N₂O₂S
• 分子量: 394.538
• InChiKey: HVWCUYXWPCFIJO-PGMHBOJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-双(3-氨基丙基)哌嗪 、 (5Z)-2-ethylsulfanyl-3-butyl-5-(4-phenylmethyloxybenzylidene)-3,5-dihydro-4H-imidazol-4-one 反应 0.5h， 以16%的产率得到N,N'-bis[(5Z)-3-butyl-5-(4-benzyloxyphenyl)methylene-4-oxo-3,5-dihydro-4H-imidazol-2-yl]-1,4-bis(3-aminopropyl)piperazine
  参考文献：
  名称：

  Synthesis of N,N′-bis(5-arylidene-4-oxo-3,5-dihydro-4H-imidazol-2-yl)diamines bearing various linkers and biological evaluation as potential inhibitors of kinases

  摘要：

  The synthesis in 4 steps of new N,N'-bis(5-arylidene-4-oxo-3,5-dihydro-4H-imidazol-2-yl)diamines issued from various symmetric primary diamines as linkers was reported. The key step of our strategy has been the sulphur/nitrogen displacement of (5Z)-5-arylidene-2-ethylsulfanyl-3,5-dihydro-4H-imidazol-4-ones 6 with respectively ethylenediamine 7a, piperazine 7b and N,N'-bis(3-aminopropyl)piperazine 7c using solvent-free reaction conditions under microwave irradiation with retention of configuration. These compounds were tested for their kinase inhibitory potencies toward four kinases (GSK-3 alpha/beta, DYRK1A, CLK1 and CLK3). Crown Copyright (C) 2012 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.044
• 作为产物：
  描述：

  1-碘丁烷 、 (Z)-5-(4-(benzyloxy)benzylidene)-3-butyl-2-thioxoimidazolidin-4-one 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以78%的产率得到(5Z)-2-ethylsulfanyl-3-butyl-5-(4-phenylmethyloxybenzylidene)-3,5-dihydro-4H-imidazol-4-one
  参考文献：
  名称：

  Synthesis of N,N′-bis(5-arylidene-4-oxo-3,5-dihydro-4H-imidazol-2-yl)diamines bearing various linkers and biological evaluation as potential inhibitors of kinases

  摘要：

  The synthesis in 4 steps of new N,N'-bis(5-arylidene-4-oxo-3,5-dihydro-4H-imidazol-2-yl)diamines issued from various symmetric primary diamines as linkers was reported. The key step of our strategy has been the sulphur/nitrogen displacement of (5Z)-5-arylidene-2-ethylsulfanyl-3,5-dihydro-4H-imidazol-4-ones 6 with respectively ethylenediamine 7a, piperazine 7b and N,N'-bis(3-aminopropyl)piperazine 7c using solvent-free reaction conditions under microwave irradiation with retention of configuration. These compounds were tested for their kinase inhibitory potencies toward four kinases (GSK-3 alpha/beta, DYRK1A, CLK1 and CLK3). Crown Copyright (C) 2012 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.044