(S)-2-(4-chlorophenyl)-2-(pyridin-3-yl)-1-[4-[5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]ethanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (S)-2-(4-chlorophenyl)-2-(pyridin-3-yl)-1-[4-[5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]ethanone
• 化学式: C₂₃H₂₀ClF₃N₄O
• 分子量: 460.886
• InChiKey: QODANUKDEHILIF-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  49.33
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-氟吡啶 在 potassium tert-butylate 、 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 、 sodium hydroxide 作用下， 以 N-甲基吡咯烷酮 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 110.0 ℃ 、10.0 MPa 条件下， 反应 3.0h， 生成 (R)-2-(4-chlorophenyl)-2-(pyridin-3-yl)-1-[4-[5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]ethanone 、 (S)-2-(4-chlorophenyl)-2-(pyridin-3-yl)-1-[4-[5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]ethanone
  参考文献：
  名称：

  Two Analogues of Fenarimol Show Curative Activity in an Experimental Model of Chagas Disease

  摘要：

  Chagas disease, caused by the protozoan parasite Trypanosoma cruzi (T. cruzi), is an increasing threat to global health. Available medicines were introduced over 40 years ago, have undesirable side effects, and give equivocal results of cure in the chronic stage of the disease. We report the development of two compounds, 6 and (S)-7, with PCR-confirmed curative activity in a mouse model of established T. cruzi infection after once daily oral dosing for 20 days at 20 mg/kg 6 and 10 mg/kg (S)-7. Compounds 6 and (S)-7 have potent in vitro activity, are noncytotoxic, show no adverse effects in vivo following repeat dosing, are prepared by a short synthetic route, and have druglike properties suitable for preclinical development.

  DOI：

  10.1021/jm401610c

文献信息

• Two Analogues of Fenarimol Show Curative Activity in an Experimental Model of Chagas Disease
  作者：Martine Keenan、Jason H. Chaplin、Paul W. Alexander、Michael J. Abbott、Wayne M. Best、Andrea Khong、Adriana Botero、Catherine Perez、Scott Cornwall、R. Andrew Thompson、Karen L. White、David M. Shackleford、Maria Koltun、Francis C. K. Chiu、Julia Morizzi、Eileen Ryan、Michael Campbell、Thomas W. von Geldern、Ivan Scandale、Eric Chatelain、Susan A. Charman

  DOI：10.1021/jm401610c

  日期：2013.12.27

  Chagas disease, caused by the protozoan parasite Trypanosoma cruzi (T. cruzi), is an increasing threat to global health. Available medicines were introduced over 40 years ago, have undesirable side effects, and give equivocal results of cure in the chronic stage of the disease. We report the development of two compounds, 6 and (S)-7, with PCR-confirmed curative activity in a mouse model of established T. cruzi infection after once daily oral dosing for 20 days at 20 mg/kg 6 and 10 mg/kg (S)-7. Compounds 6 and (S)-7 have potent in vitro activity, are noncytotoxic, show no adverse effects in vivo following repeat dosing, are prepared by a short synthetic route, and have druglike properties suitable for preclinical development.