4-(4-Chlorophenyl)-5-(4-methylsulfanylphenyl)-1,3-dihydroimidazole-2-thione | 1415020-22-2

• 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-Chlorophenyl)-5-(4-methylsulfanylphenyl)-1,3-dihydroimidazole-2-thione
• 英文别名: 4-(4-chlorophenyl)-5-(4-methylsulfanylphenyl)-1,3-dihydroimidazole-2-thione
• CAS: 1415020-22-2
• 化学式: C₁₆H₁₃ClN₂S₂
• 分子量: 332.878
• InChiKey: VAXDWOGHSOVRRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-Chlorophenyl)-5-(4-methylsulfanylphenyl)-1,3-dihydroimidazole-2-thione 、 碘甲烷 在 sodium persulfate 作用下， 以 甲醇 、 四氢呋喃 、 水 为溶剂， 反应 18.0h， 以68%的产率得到4-(4-chlorophenyl)-2-methylsulfonyl-5-(4-methylsulfonylphenyl)-1H-imidazole
  参考文献：
  名称：

  Synthesis, cyclooxygenase inhibitory effects, and molecular modeling study of 4-aryl-5-(4-(methylsulfonyl)phenyl)-2-alkylthio and -2-alkylsulfonyl-1 H -imidazole derivatives

  摘要：

  A series of 4-aryl-5-(4-(methylsulfonyl)phenyl)-2-alkylthio and 2-alkylsulfonyl-1H-imidazole derivatives were synthesized. All compounds were tested in human blood assay to determine COX-1 and COX-2 inhibitory potency and selectivity. Among the synthesized compounds, 2-alkylthio series were more potent and selective than 2-sulfonylalkyl derivatives. In molecular modeling, interaction of 2-sulfonylalkyl moiety with Arg120 in COX-1 and an extra hydrogen bond with Tyr341 in COX-2 increased the residence time of ligands in the active site in 2-sulfonylalkyl and 2-alkylthio analogs, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.058
• 作为产物：
  描述：

  2-(4-chlorophenyl)-1-(4-methylsulfanylphenyl)ethanone 在 溴 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 正丁醇 为溶剂， 生成 4-(4-Chlorophenyl)-5-(4-methylsulfanylphenyl)-1,3-dihydroimidazole-2-thione
  参考文献：
  名称：

  Synthesis, cyclooxygenase inhibitory effects, and molecular modeling study of 4-aryl-5-(4-(methylsulfonyl)phenyl)-2-alkylthio and -2-alkylsulfonyl-1 H -imidazole derivatives

  摘要：

  A series of 4-aryl-5-(4-(methylsulfonyl)phenyl)-2-alkylthio and 2-alkylsulfonyl-1H-imidazole derivatives were synthesized. All compounds were tested in human blood assay to determine COX-1 and COX-2 inhibitory potency and selectivity. Among the synthesized compounds, 2-alkylthio series were more potent and selective than 2-sulfonylalkyl derivatives. In molecular modeling, interaction of 2-sulfonylalkyl moiety with Arg120 in COX-1 and an extra hydrogen bond with Tyr341 in COX-2 increased the residence time of ligands in the active site in 2-sulfonylalkyl and 2-alkylthio analogs, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.058

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.