4-[4-(Dimethylamino)phenyl]-5-(4-methoxyphenyl)-1,3-dihydroimidazole-2-thione | 1415020-21-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[4-(Dimethylamino)phenyl]-5-(4-methoxyphenyl)-1,3-dihydroimidazole-2-thione
• CAS: 1415020-21-1
• 化学式: C₁₈H₁₉N₃OS
• 分子量: 325.434
• InChiKey: ZOMYMLDBKJPGBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  68.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  硫氰酸铵 、 2-(4-(dimethylamino)phenyl)-2-hydroxy-1-(4-methoxyphenyl)-ethan-1-one 以 正丁醇 为溶剂， 以51%的产率得到4-[4-(Dimethylamino)phenyl]-5-(4-methoxyphenyl)-1,3-dihydroimidazole-2-thione
  参考文献：
  名称：

  Synthesis and SAR study of 4,5-diaryl-1H-imidazole-2(3H)-thione derivatives, as potent 15-lipoxygenase inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2012.09.050