3-(4-(pyrrolidin-1-yl)piperidin-1-yl)-5-(trifluoromethyl)aniline | 1201593-04-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-(4-(pyrrolidin-1-yl)piperidin-1-yl)-5-(trifluoromethyl)aniline
• 英文别名: 3-(4-(Pyrrolidin-1-yl)piperidin-1-yl)-5-(trifluoromethyl)benzenamine；3-(4-pyrrolidin-1-ylpiperidin-1-yl)-5-(trifluoromethyl)aniline
• CAS: 1201593-04-5
• 化学式: C₁₆H₂₂F₃N₃
• 分子量: 313.366
• InChiKey: QPVBTKYCMSXJSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  32.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-氰基苯甲酸 、 3-(4-(pyrrolidin-1-yl)piperidin-1-yl)-5-(trifluoromethyl)aniline 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-cyano-N-(3-(4-(pyrrolidin-1-yl)piperidin-1-yl)-5-(trifluoromethyl)phenyl)benzamide
  参考文献：
  名称：

  Cell-based optimization of novel benzamides as potential antimalarial leads

  摘要：

  Screening our in-house compound collection using a cell based Plasmodium falciparum proliferation assay we discovered a known pan- kinase inhibitor scaffold as a hit. Further optimization of this series led us to a novel benzamide scaffold which was devoid of human kinase activity while retaining its antiplasmodial activity. The evolution of this compound series leading to optimized candidates with good cellular potency against multiple strains as well as decent in vivo profile is described in this Letter. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.050
• 作为产物：
  描述：

  tert-butyl N-[3-(4-pyrrolidin-1-ylpiperidin-1-yl)-5-(trifluoromethyl)phenyl]carbamate 在 三氟乙酸 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 以33%的产率得到3-(4-(pyrrolidin-1-yl)piperidin-1-yl)-5-(trifluoromethyl)aniline
  参考文献：
  名称：

  [EN] COMPOUNDS AND COMPOSITIONS USEFUL FOR THE TREATMENT OF MALARIA
  [FR] COMPOSÉS ET COMPOSITIONS UTILES POUR LE TRAITEMENT DE LA MALARIA

  摘要：

  公开号：

  WO2009152356A3

文献信息

• COMPOUNDS AND COMPOSITIONS USEFUL FOR THE TREATMENT OF MALARIA
  申请人：Chatterjee Arnab K.

  公开号：US20110144107A1

  公开（公告）日：2011-06-16

  The invention provides a class of compounds of formula I, pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent malaria.

  本发明提供了一类I式化合物，包括这些化合物的药物组合物和使用这些化合物治疗或预防疟疾的方法。
• [EN] COMPOUNDS AND COMPOSITIONS USEFUL FOR THE TREATMENT OF MALARIA<br/>[FR] COMPOSÉS ET COMPOSITIONS UTILES POUR LE TRAITEMENT DE LA MALARIA
  申请人：IRM LLC

  公开号：WO2009152356A3

  公开（公告）日：2010-02-25
• Cell-based optimization of novel benzamides as potential antimalarial leads
  作者：Tao Wu、Advait Nagle、Tomoyo Sakata、Kerstin Henson、Rachel Borboa、Zhong Chen、Kelli Kuhen、David Plouffe、Elizabeth Winzeler、Francisco Adrian、Tove Tuntland、Jonathan Chang、Susan Simerson、Steven Howard、Jared Ek、John Isbell、Xianming Deng、Nathanael S. Gray、David C. Tully、Arnab K. Chatterjee

  DOI：10.1016/j.bmcl.2009.10.050

  日期：2009.12

  Screening our in-house compound collection using a cell based Plasmodium falciparum proliferation assay we discovered a known pan- kinase inhibitor scaffold as a hit. Further optimization of this series led us to a novel benzamide scaffold which was devoid of human kinase activity while retaining its antiplasmodial activity. The evolution of this compound series leading to optimized candidates with good cellular potency against multiple strains as well as decent in vivo profile is described in this Letter. (C) 2009 Elsevier Ltd. All rights reserved.