5-methyl-4-isoxazolemethylamine | 139458-29-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-methyl-4-isoxazolemethylamine
• 英文别名: (5-Methylisoxazol-4-yl)methanamine；(5-methyl-1,2-oxazol-4-yl)methanamine
• CAS: 139458-29-0
• 化学式: C₅H₈N₂O
• 分子量: 112.131
• InChiKey: ZRIIZUYEXSYUNH-UHFFFAOYSA-N

物化性质

• 沸点：
  225.0±25.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methyl-4-isoxazolemethylamine 、 5-甲基-3-羟基环己-2-烯酮 以 乙醇 、 乙酸乙酯 为溶剂， 反应 6.0h， 以73%的产率得到3-[(5-methylisoxazol-4-yl)methylamino]-5-methylcyclohex-2-enone
  参考文献：
  名称：

  Enaminones 12. An explanation of anticonvulsant activity and toxicity per Linus Pauling’s clathrate hypothesis

  摘要：

  The x-ray crystal structure of 3-((5-methylisoxazol-3-yl)amino)-5-methylcyclohex-2-enone (12b) and 3((5-methylisoxazolyl-3-yl)amino)-5,5-dimethylcyclohex-2-enone (12c) were determined and correlated to their anticonvulsant activity in mice and rats. A hypothesis for the toxicity of the analogs are advanced. In addition, a series of 5-methyl-N-(3-oxocyclohex-1-enyl)-isoxazole-3-carboxamides were synthesized and evaluated for anticonvulsant activity. These compounds were compared to the activity of the corresponding amino and aminomethyl enaminones. Additional investigation involved the synthesis and evaluation of a trifluoromethyl analog of the active isoxazole tert-butyl 4-(5-methisoxazol-3-yl-amino)-6-methyl-2-oxo-cyclohex-3-ene carboxylate (4f). Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2012.02.003

文献信息

• Synthesis and biological evaluation of novel (4 or 5-aryl)pyrazolyl-indoles as inhibitors of interleukin-2 inducible T-cell kinase (ITK)
  作者：Avdhoot D. Velankar、Gianluca Quintini、Arati Prabhu、Alexander Weber、Gundula Hunaeus、Britta Voland、Monika Wuest、Christian Orjeda、Dipak Harel、Shaji Varghese

  DOI：10.1016/j.bmc.2010.04.056

  日期：2010.6.15

  Interleukin-2 inducible T-cell kinase (ITK) is one of five kinases that belong to the Tec kinase family that plays an important role in T-cell and mast cell signaling. Various reports point to a role of ITK in the treatment of allergic asthma. For example, it was shown that mice lacking ITK have reduced airway hyperresponsiveness, inflammation and tracheal responses in an allergic asthma model. In

  白介素2诱导型T细胞激酶（ITK）是属于Tec激酶家族的五种激酶之一，在T细胞和肥大细胞信号传导中起着重要作用。各种报道指出ITK在过敏性哮喘的治疗中的作用。例如，已表明缺乏ITK的小鼠在过敏性哮喘模型中具有降低的气道高反应性，炎症和气管反应。在本文中，我们披露了基于（4或5-芳基）吡唑基-吲哚骨架的新型ITK抑制剂，该抑制剂也被发现对ITK的选择性优于其他激酶，例如IRK，CDK2，GSK3ß和PKA。