5-(2,3-dimethoxyphenyl)-2-phenyl-1H-imidazole | 1396162-71-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(2,3-dimethoxyphenyl)-2-phenyl-1H-imidazole
• CAS: 1396162-71-2
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: ABOYVNUIOBNTPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 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：
  47.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(2,3-dimethoxyphenyl)-2-phenyl-1H-imidazole 在 盐酸 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 生成 5-(2,3-dimethoxyphenyl)-2-phenyl-1H-imidazole;hydrochloride
  参考文献：
  名称：

  Identification and characterization of diarylimidazoles as hybrid inhibitors of butyrylcholinesterase and amyloid beta fibril formation

  摘要：

  In this contribution, a chemical collection of aromatic compounds was screened for inhibition on butyrylcholinesterase (BChE)'s hydrolase activity using Ellman's reaction. A set of diarylimidazoles was identified as highly selective inhibitors of BChE hydrolase activity and amyloid beta (A beta) fibril formation. New derivatives were synthesized resulting in several additional hits, from which the most active was 6c, 4-(3-ethylthiophenyl)-2-(3-thieny1)-1H-imidazole, an uncompetitive inhibitor of BChE hydrolase activity (IC50 BChE = 0.10 mu M; K-i = 0.073 +/- 0.011 mu M) acting also on Ap fibril formation (IC50 = 5.8 mu M). With the aid of structure-activity relationship (SAR) studies, chemical motifs influencing the BChE inhibitory activity of these imidazoles were proposed. These bifunctional inhibitors represent good tools in basic studies of BChE and/or promising lead molecules for AD therapy. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2011.11.004
• 作为产物：
  描述：

  2,3-二甲氧基苯硼酸 在 盐酸 、 四(三苯基膦)钯 、 水 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 甲苯 为溶剂， 反应 32.0h， 生成 5-(2,3-dimethoxyphenyl)-2-phenyl-1H-imidazole
  参考文献：
  名称：

  Identification and characterization of diarylimidazoles as hybrid inhibitors of butyrylcholinesterase and amyloid beta fibril formation

  摘要：

  In this contribution, a chemical collection of aromatic compounds was screened for inhibition on butyrylcholinesterase (BChE)'s hydrolase activity using Ellman's reaction. A set of diarylimidazoles was identified as highly selective inhibitors of BChE hydrolase activity and amyloid beta (A beta) fibril formation. New derivatives were synthesized resulting in several additional hits, from which the most active was 6c, 4-(3-ethylthiophenyl)-2-(3-thieny1)-1H-imidazole, an uncompetitive inhibitor of BChE hydrolase activity (IC50 BChE = 0.10 mu M; K-i = 0.073 +/- 0.011 mu M) acting also on Ap fibril formation (IC50 = 5.8 mu M). With the aid of structure-activity relationship (SAR) studies, chemical motifs influencing the BChE inhibitory activity of these imidazoles were proposed. These bifunctional inhibitors represent good tools in basic studies of BChE and/or promising lead molecules for AD therapy. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2011.11.004