pyrazin-2-yl(4-(trifluoromethyl)phenyl)methanone | 1430341-45-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pyrazin-2-yl(4-(trifluoromethyl)phenyl)methanone
• 英文别名: Pyrazin-2-yl-[4-(trifluoromethyl)phenyl]methanone
• CAS: 1430341-45-9
• 化学式: C₁₂H₇F₃N₂O
• mdl: MFCD17535836
• 分子量: 252.196
• InChiKey: NSJHTSNRZIXCJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  pyrazin-2-yl(4-(trifluoromethyl)phenyl)methanone 在 sodium tetrahydroborate 、 氯化亚砜 、 potassium carbonate 、 potassium iodide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 48.0h， 生成 2-[[4-(2-Methoxyphenyl)piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methyl]pyrazine
  参考文献：
  名称：

  Design, structure–activity relationship and in vivo efficacy of piperazine analogues of fenarimol as inhibitors of Trypanosoma cruzi

  摘要：

  A scaffold hopping exercise undertaken to expand the structural diversity of the fenarimol series of anti-Trypanosoma cruzi (T. cruzi) compounds led to preparation of simple 1-[phenyl(pyridin-3-yl)methyl]piperazinyl. analogues of fenarimol which were investigated for their ability to inhibit T. cruzi in vitro in a whole organism assay. A range of compounds bearing amide, sulfonamide, carbamate/carbonate and aryl moieties exhibited low nM activities and two analogues were further studied for in vivo efficacy in a mouse model of T. cruzi infection. One compound, the citrate salt of 37, was efficacious in a mouse model of acute T. cruzi infection after once daily oral dosing at 20, 50 and 100 mg/kg for 5 days. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.050
• 作为产物：
  描述：

  4'-三氟甲基苯乙酮 在 吡啶 、 ferrous(II) sulfate heptahydrate 、 selenium(IV) oxide 、 ammonium peroxydisulfate 、 甲酸 、 二甲基亚砜 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 pyrazin-2-yl(4-(trifluoromethyl)phenyl)methanone
  参考文献：
  名称：

  铁催化α-酮酸使N-杂芳烃微缩酰化

  摘要：

  已经开发出一种有效且温和的方案，用于含氮杂芳烃与α-酮酸的Minisci酰化反应。与常规的Minisci酰化条件不同，该化学过程是使用非贵金属Fe（II）代替昂贵的Ag（I）盐作为催化剂进行的。各种底物，包括脂族或芳族α-酮酸，以及各种N-杂芳烃，都证明与该方案兼容。放大实验也证明了该方法的实用性。

  DOI：

  10.1016/j.tet.2019.01.060

文献信息

• Design, structure–activity relationship and in vivo efficacy of piperazine analogues of fenarimol as inhibitors of Trypanosoma cruzi
  作者：Martine Keenan、Paul W. Alexander、Hugo Diao、Wayne M. Best、Andrea Khong、Maria Kerfoot、R. C. Andrew Thompson、Karen L. White、David M. Shackleford、Eileen Ryan、Alison D. Gregg、Susan A. Charman、Thomas W. von Geldern、Ivan Scandale、Eric Chatelain

  DOI：10.1016/j.bmc.2013.01.050

  日期：2013.4

  A scaffold hopping exercise undertaken to expand the structural diversity of the fenarimol series of anti-Trypanosoma cruzi (T. cruzi) compounds led to preparation of simple 1-[phenyl(pyridin-3-yl)methyl]piperazinyl. analogues of fenarimol which were investigated for their ability to inhibit T. cruzi in vitro in a whole organism assay. A range of compounds bearing amide, sulfonamide, carbamate/carbonate and aryl moieties exhibited low nM activities and two analogues were further studied for in vivo efficacy in a mouse model of T. cruzi infection. One compound, the citrate salt of 37, was efficacious in a mouse model of acute T. cruzi infection after once daily oral dosing at 20, 50 and 100 mg/kg for 5 days. (C) 2013 Elsevier Ltd. All rights reserved.
• Iron-catalyzed Minisci acylation of N-heteroarenes with α-keto acids
  作者：Xiu-Zhi Wang、Cheng-Chu Zeng

  DOI：10.1016/j.tet.2019.01.060

  日期：2019.3

  protocol has been developed for the Minisci acylation reactions of nitrogen-containing heteroarenes with α-keto acids. Distinct from the conventional Minisci acylation conditions, the chemistry was performed using non-noble metal Fe(II), instead of expensive Ag(I) salt, as catalyst. A wide range of substrates, including aliphatic or aromatic α-keto acids, as well as various N-heteroarenes, proved to

  已经开发出一种有效且温和的方案，用于含氮杂芳烃与α-酮酸的Minisci酰化反应。与常规的Minisci酰化条件不同，该化学过程是使用非贵金属Fe（II）代替昂贵的Ag（I）盐作为催化剂进行的。各种底物，包括脂族或芳族α-酮酸，以及各种N-杂芳烃，都证明与该方案兼容。放大实验也证明了该方法的实用性。