4-Methyl-1-(3-methyl-5-nitrophenyl)imidazole | 1421681-15-3

• 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-Methyl-1-(3-methyl-5-nitrophenyl)imidazole
• 英文别名: 4-methyl-1-(3-methyl-5-nitrophenyl)imidazole
• CAS: 1421681-15-3
• 化学式: C₁₁H₁₁N₃O₂
• 分子量: 217.227
• InChiKey: QUBXPECHMDBASW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Methyl-1-(3-methyl-5-nitrophenyl)imidazole 在 tin(II) chloride dihdyrate 作用下， 以 甲醇 为溶剂， 生成 3-methyl-5-(4-methylimidazol-1-yl)aniline
  参考文献：
  名称：

  Synthesis and biological evaluation of analogues of the kinase inhibitor nilotinib as Abl and Kit inhibitors

  摘要：

  The importance of the trifluoromethyl group in the polypharmacological profile of nilotinib was investigated. Molecular editing of nilotinib led to the design, synthesis and biological evaluation of analogues where the trifluoromethyl group was replaced by a proton, fluorine and a methyl group. While these analogues were less active than nilotinib toward Abl, their activity toward Kit was comparable, with the monofluorinated analogue being the most active. Docking of nilotinib and of analogues 2a-c to the binding pocket of Abl and of Kit showed that the lack of shape complementarity in Kit is compensated by the stabilizing effect from its juxtamembrane region. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.11.111
• 作为产物：
  描述：

  4-甲基咪唑 、 3-碘-5-硝基甲苯 在 copper(I) oxide 、 4,7-二甲氧基-1,10-菲咯啉 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 生成 4-Methyl-1-(3-methyl-5-nitrophenyl)imidazole
  参考文献：
  名称：

  Synthesis and biological evaluation of analogues of the kinase inhibitor nilotinib as Abl and Kit inhibitors

  摘要：

  The importance of the trifluoromethyl group in the polypharmacological profile of nilotinib was investigated. Molecular editing of nilotinib led to the design, synthesis and biological evaluation of analogues where the trifluoromethyl group was replaced by a proton, fluorine and a methyl group. While these analogues were less active than nilotinib toward Abl, their activity toward Kit was comparable, with the monofluorinated analogue being the most active. Docking of nilotinib and of analogues 2a-c to the binding pocket of Abl and of Kit showed that the lack of shape complementarity in Kit is compensated by the stabilizing effect from its juxtamembrane region. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.11.111

文献信息

• Synthesis and biological evaluation of analogues of the kinase inhibitor nilotinib as Abl and Kit inhibitors
  作者：Damien Y. Duveau、Xin Hu、Martin J. Walsh、Suneet Shukla、Amanda P. Skoumbourdis、Matthew B. Boxer、Suresh V. Ambudkar、Min Shen、Craig J. Thomas

  DOI：10.1016/j.bmcl.2012.11.111

  日期：2013.2

  The importance of the trifluoromethyl group in the polypharmacological profile of nilotinib was investigated. Molecular editing of nilotinib led to the design, synthesis and biological evaluation of analogues where the trifluoromethyl group was replaced by a proton, fluorine and a methyl group. While these analogues were less active than nilotinib toward Abl, their activity toward Kit was comparable, with the monofluorinated analogue being the most active. Docking of nilotinib and of analogues 2a-c to the binding pocket of Abl and of Kit showed that the lack of shape complementarity in Kit is compensated by the stabilizing effect from its juxtamembrane region. Published by Elsevier Ltd.