1-[4-[(4-Chloro-2-fluorophenyl)-pyridin-3-ylmethyl]piperazin-1-yl]-2,2-dimethylpropan-1-one | 1430340-77-4

• 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: 1-[4-[(4-Chloro-2-fluorophenyl)-pyridin-3-ylmethyl]piperazin-1-yl]-2,2-dimethylpropan-1-one
• CAS: 1430340-77-4
• 化学式: C₂₁H₂₅ClFN₃O
• 分子量: 389.9
• InChiKey: PHURSCYDIHRUEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  36.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-[chloro(4-chloro-2-fluorophenyl)methyl]pyridine 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 potassium iodide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 120.0h， 生成 1-[4-[(4-Chloro-2-fluorophenyl)-pyridin-3-ylmethyl]piperazin-1-yl]-2,2-dimethylpropan-1-one
  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

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.