5-(4-chlorophenyl)-4-(4-methoxyphenyl)-2-(methylthio)-1H-imidazole | 1415020-23-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-chlorophenyl)-4-(4-methoxyphenyl)-2-(methylthio)-1H-imidazole
• 英文别名: 5-(4-chlorophenyl)-4-(4-methoxyphenyl)-2-methylsulfanyl-1H-imidazole
• CAS: 1415020-23-3
• 化学式: C₁₇H₁₅ClN₂OS
• 分子量: 330.838
• InChiKey: SSBRSSYIURUHLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-4-(4-methoxyphenyl)-2-(methylthio)-1H-imidazole 、 N,N-二甲基甲酰胺二甲基缩醛 以 甲苯 为溶剂， 反应 24.0h， 以25%的产率得到5-(4-chlorophenyl)-4-(4-methoxyphenyl)-1-methyl-2-(methylthio)-1H-imidazole
  参考文献：
  名称：

  Convenient and Regiospecific Method for Synthesis of 4,5-Diaryl-1-methyl-2-(methylthio)-1H-imidazole

  摘要：

  A convenient, high-yielding, regiospecific synthesis of 1H-imidazole-2-thiones ring has been developed. In addition, a series of 4,5-diaryl-1-methyl-2-(methylthio)-1H-imidazoles 8 were synthesized and characterized. The structure of regioisomers was confirmed through nuclear Overhauser effect spectroscopy and NMR spectroscopy. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.717670
• 作为产物：
  描述：

  2-(4-氯苯基)-2-羟基-1-(4-甲氧基苯基)乙酮 在 三乙胺 作用下， 以 甲醇 、 正丁醇 为溶剂， 反应 2.0h， 生成 5-(4-chlorophenyl)-4-(4-methoxyphenyl)-2-(methylthio)-1H-imidazole
  参考文献：
  名称：

  Convenient and Regiospecific Method for Synthesis of 4,5-Diaryl-1-methyl-2-(methylthio)-1H-imidazole

  摘要：

  A convenient, high-yielding, regiospecific synthesis of 1H-imidazole-2-thiones ring has been developed. In addition, a series of 4,5-diaryl-1-methyl-2-(methylthio)-1H-imidazoles 8 were synthesized and characterized. The structure of regioisomers was confirmed through nuclear Overhauser effect spectroscopy and NMR spectroscopy. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.717670

文献信息

• Synthesis and SAR study of 4,5-diaryl-1H-imidazole-2(3H)-thione derivatives, as potent 15-lipoxygenase inhibitors
  作者：Amir Assadieskandar、Mohsen Amini、Marjan Salehi、Hamid Sadeghian、Maliheh Alimardani、Amirhossein Sakhteman、Hamid Nadri、Abbas Shafiee

  DOI：10.1016/j.bmc.2012.09.050

  日期：2012.12

  A series of 4,5-diaryl-1H-imidazole-2(3H)-thione was synthesized and their inhibitory potency against soybean 15-lipoxygenase and free radical scavenging activities were determined. Compound 11 showed the best IC50 for 15-LOX inhibition (IC50 = 4.7 mu M) and free radical scavenging activity (IC50 = 14 mu M). Methylation of SH at C-2 position of imidazole has dramatically decreased the 15-LOX inhibition and radical scavenging activity as it can be observed in the inactive compound 14 (IC50 >250 mu M). Structure activity similarity (SAS) showed that the most important chemical modification in this series was methylation of SH group and Docking studies revealed a proper orientation for SH group towards Fe core of the 15-LOX active site. Therefore it was concluded that iron chelating could be a possible mechanism for enzyme inhibition in this series of compounds. (C) 2012 Elsevier Ltd. All rights reserved.