2-氨基-4-((三甲基甲硅烷基)乙炔基)嘧啶 | 1214264-40-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2-氨基-4-((三甲基甲硅烷基)乙炔基)嘧啶
• 英文名称: 4-((trimethylsilyl)ethynyl)pyrimidin-2-amine
• 英文别名: 2-amino-4-((trimethylsilyl)ethynyl)pyrimidine；2-Amino-4-(trimethylsilylethynyl)pyrimidine；4-(2-trimethylsilylethynyl)pyrimidin-2-amine
• CAS: 1214264-40-0
• 化学式: C₉H₁₃N₃Si
• 分子量: 191.308
• InChiKey: MPAKPCMZMBHQHS-UHFFFAOYSA-N

物化性质

• 熔点：
  117 °C
• 沸点：
  305.5±48.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氨基-4-((三甲基甲硅烷基)乙炔基)嘧啶 在 copper(ll) sulfate pentahydrate 、 四丁基氟化铵 、 sodium ascorbate 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 72.5h， 生成 diethyl (2-(4-(2-(4-fluorophenyl)-3-(2-(methylthio)pyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-yl)-1H-1,2,3-triazol-1-yl)ethyl)phosphonate
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 4-fluorophenyl-imidazole p38α MAPK, CK1δ and JAK2 kinase inhibitors

  摘要：

  The synthesis and structure-activity relationships of novel 4-(4 '-fluorophenyl)imidazoles as selective p38 alpha MAPK, CK1 delta and JAK2 inhibitors with improved water solubility are described. Microwave-assisted multicomponent reactions afforded 4-fluorophenyl-2,5-disubstituted imidazoles. Carboxylate and phosphonate groups were introduced via 'click' reactions. The kinase selectivity was influenced by the heteroaryl group at imidazole C-5 and the position of a carboxylic acid or tetrazole at imidazole C-2. For example, pyrimidines 15 and 34 inhibited p38 alpha MAPK with IC50 = 250 nM and 96 nM, respectively. Pyridine 3 gave CK1 delta inhibition with IC50 = 89 nM and pyridin-2-one 31 gave JAK2 inhibition with IC50 = 62 nM. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.080
• 作为产物：
  描述：

  2-氨基-4-氯嘧啶 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到2-氨基-4-((三甲基甲硅烷基)乙炔基)嘧啶
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 4-fluorophenyl-imidazole p38α MAPK, CK1δ and JAK2 kinase inhibitors

  摘要：

  The synthesis and structure-activity relationships of novel 4-(4 '-fluorophenyl)imidazoles as selective p38 alpha MAPK, CK1 delta and JAK2 inhibitors with improved water solubility are described. Microwave-assisted multicomponent reactions afforded 4-fluorophenyl-2,5-disubstituted imidazoles. Carboxylate and phosphonate groups were introduced via 'click' reactions. The kinase selectivity was influenced by the heteroaryl group at imidazole C-5 and the position of a carboxylic acid or tetrazole at imidazole C-2. For example, pyrimidines 15 and 34 inhibited p38 alpha MAPK with IC50 = 250 nM and 96 nM, respectively. Pyridine 3 gave CK1 delta inhibition with IC50 = 89 nM and pyridin-2-one 31 gave JAK2 inhibition with IC50 = 62 nM. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.080

文献信息

• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSES CHIMIQUES
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2005016914A1

  公开（公告）日：2005-02-24

  The present invention discloses pyrimidine derivatives, compositions and medicaments containing the same, as well as processes for the preparation and use of such compounds, compositions and medicaments. Such pyrimidine derivatives are useful in the treatment of diseases associated with inappropriate ErbB family kinase.

  本发明公开了嘧啶衍生物，含有该嘧啶衍生物的组合物和药物，以及制备和使用这些化合物、组合物和药物的方法。这些嘧啶衍生物在治疗与不适当的ErbB家族激酶相关的疾病中很有用。
• One-pot synthesis of meridianins and meridianin analogues via indolization of nitrosoarenes
  作者：Francesco Tibiletti、Marco Simonetti、Kenneth M. Nicholas、Giovanni Palmisano、Matteo Parravicini、Federico Imbesi、Stefano Tollari、Andrea Penoni

  DOI：10.1016/j.tet.2009.12.020

  日期：2010.2

  Meridianins, marine alkaloids known as kinase Inhibitors with an indole skeleton, and meridianin analogues were produced regioselectivity and in moderate to good yields by thermal annulation of nitrosoarenes with 2-amino-4-ethynylpyrimidine and 2-chloro-4-ethynylpyrimidine, respectively, through a novel and atom-economical indolization process (C) 2009 Elsevier Ltd All rights reserved