4-(4-(methylsulfonyl)phenyl)-5-phenyl-1,3-dihydro-2H-imidazole-2-thione | 1429184-66-6

• 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-(methylsulfonyl)phenyl)-5-phenyl-1,3-dihydro-2H-imidazole-2-thione
• CAS: 1429184-66-6
• 化学式: C₁₆H₁₄N₂O₂S₂
• 分子量: 330.431
• InChiKey: LSEJTAIECCOBLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  65.72
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(4-(methylsulfonyl)phenyl)-5-phenyl-1,3-dihydro-2H-imidazole-2-thione 、 碘甲烷 以 甲醇 为溶剂， 以78%的产率得到4-(4-chlorophenyl)-2-methylsulfanyl-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：

  乙酮,2-溴-1-[4-(甲硫基)苯基]-2-苯基- 在 sodium persulfate 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 18.0h， 生成 4-(4-(methylsulfonyl)phenyl)-5-phenyl-1,3-dihydro-2H-imidazole-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