1-(4-chlorophenyl)-2-(4-(methylsulfonyl)phenyl)-4,5,6,7-tetrahydro-1H-benzo[d]imidazole | 1326717-28-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-chlorophenyl)-2-(4-(methylsulfonyl)phenyl)-4,5,6,7-tetrahydro-1H-benzo[d]imidazole
• 英文别名: 1-(4-Chlorophenyl)-2-(4-methylsulfonylphenyl)-4,5,6,7-tetrahydrobenzimidazole
• CAS: 1326717-28-5
• 化学式: C₂₀H₁₉ClN₂O₂S
• 分子量: 386.902
• InChiKey: FATSHCYJTBOXKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 Oxone 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 1-(4-chlorophenyl)-2-(4-(methylsulfonyl)phenyl)-4,5,6,7-tetrahydro-1H-benzo[d]imidazole
  参考文献：
  名称：

  Design and synthesis of new 1,2-diaryl-4,5,6,7-tetrahydro-1H-benzo[d] imidazoles as selective cyclooxygenase (COX-2) inhibitors

  摘要：

  A new series of 1,2-diaryl-4,5,6,7-tetrahydro-1H-benzo[d]imidazoles, possessing a methylsulfonyl pharmacophore, were synthesized to evaluate their biological activities as selective cyclooxygenase-2 (COX-2) inhibitors. In vitro COX-1 and COX-2 isozyme inhibition studies were carried out to acquire structure-activity relationship data with respect to the point that molecular modeling studies showed that designed compounds bind in the primary binding site such that the SO2Me substituent at para-position of C-2 phenyl ring inserts into the 2A degrees pocket present in COX-2 enzyme. COX-1 and COX-2 inhibition studies showed that all compounds were selective inhibitors of the COX-2 isozyme with IC50 values in the highly potent 0.34-0.69 mu M range, and COX-2 selectivity indexes in the 52.3-163.8 range. 1-(4-Fluorophenyl)-2-(4-(methylsulfonyl)phenyl)-4,5,6,7-tetrahydro-1H-benzo[d] imidazole was identified as the most potent (IC50 = 0.34 mu M), and selective (SI = 163.8), COX-2 inhibitor among the synthesized compounds.

  DOI：

  10.1007/s00044-011-9709-y