2-Methyl-4-(3-nitro-phenylethynyl)-thiazole | 823199-07-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Methyl-4-(3-nitro-phenylethynyl)-thiazole
• 英文别名: 2-Methyl-4-[(3-nitrophenyl)ethynyl]-1,3-thiazole；2-methyl-4-[2-(3-nitrophenyl)ethynyl]-1,3-thiazole
• CAS: 823199-07-1
• 化学式: C₁₂H₈N₂O₂S
• 分子量: 244.274
• InChiKey: WRUXBWXDEVLYJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  87
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-碘-3-硝基苯 、 2-甲基-4-三甲基硅乙炔基噻唑 在 双三苯基磷二氯化钯 copper(l) iodide 、 四丁基氟化铵 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以76%的产率得到2-Methyl-4-(3-nitro-phenylethynyl)-thiazole
  参考文献：
  名称：

  Synthesis and receptor assay of aromatic–ethynyl–aromatic derivatives with potent mGluR5 antagonist activity

  摘要：

  Noncompetitive antagonists of the human metabotropic glutamate receptor subtype 5 (mGluR5) have been implicated as potential therapeutics for the treatment of a variety of nervous system disorders, including pain, anxiety, and drug addiction. To discover novel noncompetitive antagonists to the mGluR5, we initiated an SAR study around the known lead compounds MPEP and M-MPEP. Our results pointed out the critical role of the para position of the two aromatic rings, which leads to inactive products and permitted the discovery of potent mGluR5 antagonists (e.g., 16, 25, 28, 34 IC50 = 13.5, 11.9, 21, 15nM, respectively). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.042

文献信息

• Synthesis and receptor assay of aromatic–ethynyl–aromatic derivatives with potent mGluR5 antagonist activity
  作者：David Alagille、Ronald M. Baldwin、Bryan L. Roth、Jarda T. Wroblewski、Ewa Grajkowska、Gilles D. Tamagnan

  DOI：10.1016/j.bmc.2004.09.042

  日期：2005.1

  Noncompetitive antagonists of the human metabotropic glutamate receptor subtype 5 (mGluR5) have been implicated as potential therapeutics for the treatment of a variety of nervous system disorders, including pain, anxiety, and drug addiction. To discover novel noncompetitive antagonists to the mGluR5, we initiated an SAR study around the known lead compounds MPEP and M-MPEP. Our results pointed out the critical role of the para position of the two aromatic rings, which leads to inactive products and permitted the discovery of potent mGluR5 antagonists (e.g., 16, 25, 28, 34 IC50 = 13.5, 11.9, 21, 15nM, respectively). (C) 2004 Elsevier Ltd. All rights reserved.