1-((R)-3-(4-(trifluoromethyl)phenoxy)-2-hydroxypropyl)-4-(4-chloro-3-(trifluoromethyl)phenyl)piperidin-4-ol | 1166991-34-9

• 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: 1-((R)-3-(4-(trifluoromethyl)phenoxy)-2-hydroxypropyl)-4-(4-chloro-3-(trifluoromethyl)phenyl)piperidin-4-ol
• 英文别名: 4-[4-chloro-3-(trifluoromethyl)phenyl]-1-[(2R)-2-hydroxy-3-[4-(trifluoromethyl)phenoxy]propyl]piperidin-4-ol
• CAS: 1166991-34-9
• 化学式: C₂₂H₂₂ClF₆NO₃
• 分子量: 497.865
• InChiKey: ITPKSFPOKCAQLA-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  52.9
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  (S)-2-((4-(三氟甲基)苯氧基)甲基)环氧乙烷 、 4-[4-氯-3-(三氟甲基)苯基]-4-哌啶醇 以 乙醇 为溶剂， 以0.21 g的产率得到1-((R)-3-(4-(trifluoromethyl)phenoxy)-2-hydroxypropyl)-4-(4-chloro-3-(trifluoromethyl)phenyl)piperidin-4-ol
  参考文献：
  名称：

  Discovery, synthesis, and biological evaluation of piperidinol analogs with anti-tuberculosis activity

  摘要：

  Direct anti-tuberculosis screening of commercially available compound libraries identified a novel piperidinol with interesting anti-tuberculosis activity and drug like characteristics. To generate a structure activity relationship about this hit a 22 member optimization library was generated using parallel synthesis. Products of this library 1-((R)-3-(4-chlorophenoxy)-2-hydroxypropyl)-4-(4-chloro-3-(trifluoromethyl) phenyl) piperidin-4-ol and 1-((S)-3-(4-(trifluoromethyl) phenoxy)-2-hydroxypropyl)-4-(4-chloro-3-( trifluoromethyl) phenyl) piperidin-4-ol demonstrated good anti-tuberculosis activity. Unfortunately, side effects were observed upon in vivo anti-tuberculosis testing of these compounds precluding their further advancement, which may be in part due to the secondary pharmacology associated with the aryl piperidinol core. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.005

文献信息

• Discovery, synthesis, and biological evaluation of piperidinol analogs with anti-tuberculosis activity
  作者：Dianqing Sun、Michael S. Scherman、Victoria Jones、Julian G. Hurdle、Lisa K. Woolhiser、Susan E. Knudson、Anne J. Lenaerts、Richard A. Slayden、Michael R. McNeil、Richard E. Lee

  DOI：10.1016/j.bmc.2009.04.005

  日期：2009.5

  Direct anti-tuberculosis screening of commercially available compound libraries identified a novel piperidinol with interesting anti-tuberculosis activity and drug like characteristics. To generate a structure activity relationship about this hit a 22 member optimization library was generated using parallel synthesis. Products of this library 1-((R)-3-(4-chlorophenoxy)-2-hydroxypropyl)-4-(4-chloro-3-(trifluoromethyl) phenyl) piperidin-4-ol and 1-((S)-3-(4-(trifluoromethyl) phenoxy)-2-hydroxypropyl)-4-(4-chloro-3-( trifluoromethyl) phenyl) piperidin-4-ol demonstrated good anti-tuberculosis activity. Unfortunately, side effects were observed upon in vivo anti-tuberculosis testing of these compounds precluding their further advancement, which may be in part due to the secondary pharmacology associated with the aryl piperidinol core. (C) 2009 Elsevier Ltd. All rights reserved.